“Can I book this on points?”

Sometimes for IHG, Hyatt, Marriott, and Hilton, the answer is yes.

The better question, though, is whether you should.

One thing I’ve noticed after years of collecting points is that many people become so focused on avoiding cash that they stop thinking about value altogether. If a hotel stay costs 700,000 points instead of $7,000, it feels like a win because no money is leaving your bank account.

But points aren’t free. They have value well beyond a 1:100 ratio when used right.

And sometimes spending points is actually more painful than spending cash. Let me explain:

The Kona Village Example

Let’s say you’re looking at a five-night stay at Kona Village, A Rosewood Resort.

Depending on the season, that stay could easily cost $6,000-$8,000.

Since Rosewood doesn’t have a loyalty program and there’s no way to get status, the only realistic way to use points is through a credit card travel portal, where points essentially act as cash.

Many people see that and think they’ve found a loophole.

I see something different.

I see 700,000 points disappearing.

Why That Number Matters, and What We Save Our Points For

Whenever I look at a redemption, I ask myself what I had to do to earn those points. Seven hundred thousand transferable points is not a small amount.

For many families, that’s years of credit card spending. Once I started thinking about points that way, I became much more selective about how I used them. Because while I can always earn more money, rebuilding a massive points balance takes time.

Personally, I don’t get excited about redeeming hundreds of thousands of points for a hotel room. I get excited about experiences I would almost never pay cash for.

For our family, that usually means long-haul business class flights – here’s how I find and book them.

A few years ago, we used transferred points to fly to Flying Blue in business class as a family of three from San Francisco to Athens and back for a Greece island hopping trip. The flight was more than 12 hours long, and everyone had a lie-flat seat with a closing door, food whenever we wanted it, lounge access, and a MUCH easier time adjusting to sleep schedules.

Had we paid cash, the flights would have cost roughly $15,000-$21,000 total.

That’s the kind of redemption that gets my attention, because wouldn’t you rather get $21k of value vs. just $7000?

Plus, there’s another caveat you’re not considering when booking through points portals – the free nights you could get that are only available through travel agents.

What We Do Instead

Rather than spending hundreds of thousands of points on hotels, we typically pay cash and book through preferred partner programs. For Rosewood properties, that means Rosewood Elite, and quite often, Rosewood Elite agents have access to free nights that aren’t always publicly available.

Benefits typically include:

• 🌺 Daily breakfast for two (often $120+ daily value)
• 💰 $150+ property credit
• ⬆️ Room upgrade when available
• ⏰ Early check-in when available
• 🌅 Late checkout when available
• ⭐ VIP recognition

In many cases, those perks can add hundreds to thousands of dollars of value to a stay while allowing us to preserve our points balance for flights, while also giving us access to free nights.

Why Luxury Hotels Are Different

Maybe the simplest way to explain it is this:

I don’t use points to avoid spending money, I use points to access experiences I would never buy with money, which is a completely different mindset.

When I look at a luxury hotel, I don’t immediately ask how many points it costs, I ask whether that’s the best use of those points.

Most of the time, the answer is no.

Which is why you’ll usually find us transferring our points to airlines and paying cash for hotels instead.

If I want to stay at Kona Village, I can make that decision and pay for it. It’s expensive, but it’s attainable, but spending $20,000 on airfare for my family isn’t something I realistically do more than once every couple of years.

That’s why flights win almost every time. Points allow us to experience something we otherwise wouldn’t.

The answer is technically yes, but it’s probably not the redemption you want to make.

Unlike Hyatt, Marriott, Hilton, and IHG, Four Seasons doesn’t have a loyalty program, and there is no such thing as status unless you’re a seriously high roller, and most loyal guests never get an invite to that particular echelon.

There are no free night certificates, no award charts, and no way to transfer points directly into a Four Seasons account. The only way to use points for a Four Seasons stay is typically through a credit card travel portal, where your points function more like cash.

While that sounds appealing on the surface, the value is usually extremely poor compared to what those same points could do elsewhere.

Let me show you what I mean.

The Four Seasons Hualalai Example

Let’s use one of my favorite resorts in Hawaii as an example.

A five-night stay at Four Seasons Hualalai can easily cost around $6,500, depending on the season and room category. If you wanted to cover that stay entirely with points through a credit card portal, you’d likely need somewhere around 650,000 transferable points.

At first glance, a free $6,500 hotel stay sounds pretty great.

But here’s what I always ask myself: What else could those points do?

What 650,000 Points Could Buy Instead

This March, our family of 3 flew round trip from San Francisco to Singapore in business class using credit card points I’d transferred directly to Singapore Airlines. We actually never fly over 6 hours in coach, and I do it almost entirely on points – points I wouldn’t have if I used them for meager hotel redemptions (more on how that works here).

This wasn’t a quick domestic flight. This was a 16+ hour international flight in lie-flat seats, with lounge access, excellent food, and enough room to actually sleep.

Had we paid cash, those tickets would have cost somewhere in the neighborhood of $5,000 to $15,000 per person.

For a family of three, that’s roughly $15,000 to $45,000 worth of flights.

The same 650,000 points that could have covered a $6,500 Four Seasons stay instead got us across the world in a way we never would have paid for out of pocket.

So why offset hotel room costs for a value of $6500 when you can get $45k of value instead??

That’s why I always recommend using transferable points for flights rather than luxury hotels.

Why Points Are Usually Better for Flights

Most people can justify spending money on a hotel.

Maybe not every year, and maybe not at Four Seasons prices, but hotels are often the part of a trip people are willing to splurge on.

Business class flights are different.

Spending $5,000 to $7,000 per person on airfare is something most travelers would never do, no matter how nice the experience is.

That’s where points become incredibly powerful.

Instead of saving a few thousand dollars on a hotel, you can unlock an experience that would otherwise feel completely out of reach.

Whenever I’m deciding how to use transferable points, I ask myself one simple question:

Would I rather have something I could eventually pay for, or something I’d probably never buy with cash?

The answer is almost always flights.

What We Do Instead

Personally, I’d rather pay cash for a Four Seasons hotel and save my points for premium cabin flights.

That approach also allows us to take advantage of Four Seasons Preferred Partner benefits, which can add a surprising amount of value to a stay.

When clients book through us as a Four Seasons Preferred Partner, they typically receive:

• 🌺 Daily breakfast for two (often $120+ daily value)
• 💰 $100+ Resort credit
• ⬆️ Room upgrades when available (and we’ve gotten them plenty!)
• ⏰ Early check-in when available
• 🌅 Late checkout when available
• ⭐ VIP recognition throughout the stay

At many Four Seasons properties, breakfast alone can easily save hundreds of dollars over the course of a trip, and room upgrades can make an even bigger difference.

Unlike points bookings through a travel portal, these benefits are designed specifically for Four Seasons guests and are only available through Four Seasons Preferred Partners, which I happen to be! Best of all, the booking is still made via the Four Seasons website, just with our agent login, and your booking and credit card charge will still come directly from the Four Seasons itself – no third party.

When It Might Make Sense to Use Points

If you have a massive stash of points, don’t travel internationally, rarely fly business class, or simply prefer hotel stays over flights, then using points through a credit card portal can absolutely make sense.

Points are only valuable if they help you travel in a way that makes you happy.

But if your goal is maximizing value, it’s hard to ignore the difference.

Would I rather spend 650,000 points on a $6,500 hotel stay?

Or use those same points to potentially unlock $15,000 to $20,000 worth of international business class flights?

For our family, the answer is easy.

My Take

I love Four Seasons hotels. They’re some of my favorite properties in the world, and I happily pay cash to stay at them and earn 3x points on my card of choice to buy more flights with.

What I don’t love is spending hundreds of thousands of transferable points on hotel rooms when those same points could unlock experiences that would otherwise be unattainable.

So while there technically is a way to book Four Seasons on points, I almost never recommend it.

Use your points for the flights, use cash for the hotel, then let a Preferred Partner advisor add the perks.

That’s the strategy we’ve used for years, and it’s one of the biggest reasons we’ve been able to stretch both our travel budget and our points so much further.

It’s because almost everything here is done exceptionally well. The grounds are beautiful, the restaurants are consistently excellent, and somehow the resort manages to feel both family-friendly and incredibly luxurious at the same time.

After multiple Four Seasons stays over the years, it’s still the resort I find myself comparing others to.

Why Book Four Seasons Hualalai With Us?

As a Four Seasons Preferred Partner, we can add complimentary perks to eligible stays at no additional cost to you. It’s still a direct FS booking, just done through the agent portal, and your booking and room charge will be entirely handled by Four Seasons, just with extra perks you wouldn’t have without an advisor.

Benefits typically include:

• 🌺 Daily breakfast for two ($120 daily value)
• 💰 $100+ Hotel credit
• ⬆️ Priority for room upgrades
• ⏰ Early check-in when available
• 🌅 Late checkout when available
• ⭐ VIP recognition throughout your stay

Because we work closely with luxury family travelers, we’re also happy to help you compare Hualalai with Kona Village, Mauna Lani, Fairmont Orchid, and other Big Island resorts to determine which one is the best fit for your trip.

What Makes Hualalai Special

There are plenty of beautiful resorts in Hawaii, but Hualalai has a way of making everything feel effortless.

The grounds are immaculate, service is attentive, and every detail seems carefully considered, yet nothing feels forced.

At some luxury resorts, you’ll have one amazing meal and one disappointing one. One staff member will be incredible and another forgettable. At Hualalai, the experience feels remarkably consistent from start to finish. That said, the absolute, hands down, best service I’ve ever experienced at a Four Seasons was at Four Seasons Maui, where not a single thing was out of place. There were a few minor hiccups at Hualalai, like luggage delivery taking a while, that made us feel it a bit more when the resort was at capacity vs. Maui.

It’s also one of the few resorts where I regularly hear people say they return year after year and stay nowhere else, and after spending time here, I understand why.

Why Families Love It

Even though Hualalai is often associated with luxury travelers and honeymooners, I think it’s one of the best family resorts in Hawaii.

The resort does an excellent job of creating experiences that appeal to children without making the property feel overwhelmingly kid-focused.

One of the biggest draws is the variety of pools. Instead of everyone gathering in one central location, guests spread out across multiple pool areas, each with its own atmosphere. There’s also a built in lagoon in the ocean as well to keep swimming easy and accessible.

Families naturally gravitate toward the King’s Pond and Sea Shell Pool areas, where there is plenty of space for kids to swim and play. I thought it was SO cool that the king’s pond was full of fish and an eagle ray. At 3, my son is a bit too young to snorkel, but my partner and I kept exclaiming to each other that we would have been in there all day long as 6-12 year olds.

The complimentary Kids For All Seasons program is available for children ages 5 to 12 and consistently receives rave reviews from families. Activities often incorporate Hawaiian culture, outdoor exploration, crafts, and games rather than relying on screens to keep kids entertained.

We also got a cute mini bathrobe, slippers, string backpack, stuffy, turtle toy, and a coupon personalized with our son’s name for a free shave ice. I love that there is enough to keep children happy without parents feeling like they’re staying at a theme park.

The Rooms

Accommodations at Hualalai are spread throughout two-story bungalow-style buildings that blend beautifully into the landscape.

The rooms have been refreshed over the years and feel bright, comfortable, and if you happen to be on the ground floor, you’ll have a lava rock outdoor shower that we loved. They have couches as well, so you can easily get that king room and use a pull out couch for your little one.

Many accommodations offer outdoor living space, and even entry-level room categories feel generous compared to what you’ll find at many other luxury resorts. That said, our ‘ocean view’ room had barely a sliver of an ocean view, so opt for the prime or above category if you want to be able to actually see it.

For larger families, there are suites and villas that provide significantly more space and privacy, and they tend to be the options right on the beach. Many have their own pools as well.

One thing I always recommend is paying close attention to room location. The resort is large enough that proximity to pools, restaurants, and the beach can make a meaningful difference depending on your travel style. For example, golf course view rooms are set pretty far back in the resort, so at least a partial ocean view will get you much closer to the pools, beach, and restaurant.

King’s Pond

If there’s one feature that has become synonymous with Hualalai, it’s King’s Pond.

This 1.8-million-gallon swimmable aquarium is built into natural lava rock and filled with thousands of tropical fish. Guests can snorkel directly in the pond and get an up-close look at marine life without ever leaving the resort.

I’ve never seen another feature quite like it.

For kids especially, it often becomes the highlight of the trip. There aren’t many places where you can wake up, walk down from your room, and snorkel alongside colorful fish before breakfast.

Even after multiple visits, it remains one of the most unique amenities I’ve encountered at any resort.

The Beach

The beach at Hualalai is beautiful, but I wouldn’t consider it the strongest beach on the island.

What makes it special is the setting rather than the size.

The crescent-shaped shoreline framed by black lava rock feels quintessentially Hawaiian, and it’s a wonderful place to watch the sunset. Depending on conditions, guests can swim, paddleboard, kayak, and snorkel directly from the beach.

That said, if your primary goal is spending all day on a wide sandy beach, I generally think Mauna Lani has the advantage.

The Food

The resort has several excellent restaurants, and based on the two we tried (Ulu and Beach Tree), the food was great, but expect to pay $50-$100 for a main. Kids at only these two restaurants eat free provided they are under 4, though you may have to remind the staff to comp them on the bill.

We loved that both of these restaurants are beachfront, so kids tend to play in the sand between bites.

Is Four Seasons Hualalai Worth It?

Hualalai is expensive. There is no getting around that.

But unlike some luxury resorts where you leave wondering what exactly you paid for, Hualalai generally delivers on the promise.

If you’re looking for the most peaceful resort on the island, I would probably steer you toward Kona Village.

If you’re looking for the best value for families, Mauna Lani is incredibly compelling.

If you’re looking for the resort that does almost everything exceptionally well, Four Seasons Hualalai remains the benchmark.

Part of that comes down to value. While Hawaii luxury resorts are never inexpensive, I think Mauna Lani delivers a lot for the price, particularly when compared to some of its neighbors. Between the family-friendly pools, swimmable beach, excellent snorkeling, spacious accommodations, and thoughtful service, it manages to check a lot of boxes without feeling overly formal or intimidating.

After our most recent stay, I was reminded why so many families return year after year. Here’s what to know and how to book for amenities like free room upgrades:

How to get VIP Auberge Perks Free of Charge

As an Auberge Preferred partner, we’re able to offer our clients additional perks at no extra cost when booking eligible stays (more about how it works here).

Benefits typically include:

• 🌺 Daily breakfast for two
• 💰 $100 resort credit
• ⬆️ Room upgrades when available
• ⏰ Early check-in when available
• 🌅 Late checkout when available

Because we specialize in luxury family travel, we’re also happy to help you decide between Mauna Lani, Kona Village, Four Seasons Hualalai, Fairmont Orchid, and other Big Island resorts to make sure you’re choosing the best fit for your family.

What Makes Mauna Lani Special

While many luxury resorts on the Big Island focus on exclusivity, Mauna Lani feels approachable.

The grounds are beautiful, the staff are warm and welcoming, and the atmosphere strikes a nice balance between luxury and relaxation. It’s the kind of place where you’ll see couples celebrating anniversaries, grandparents traveling with grandchildren, and families spending all day by the pool.

One of my favorite things about the property is its location along a protected bay. The water tends to be calmer than many other beaches on the Big Island, making it especially appealing for families with younger children.

If you’re lucky, you may even spot sea turtles resting directly on the sand. During our stay, we saw one resting on the sand and watched him from a respectful distance.

Why Families Love It

As someone who travels almost exclusively with a child these days, I pay close attention to whether a resort genuinely works for families or simply markets itself that way, and Mauna Lani absolutely delivers (as do these Hawaii resorts).

One of my favorite features is the children’s sandy-bottom pool area. Instead of a traditional splash pad or water playground, there’s a shallow sandy pool complete with adorable mini cabanas that feel perfectly sized for younger kids. It became one of my son’s favorite places on the property.

The main pool is large enough that it never feels crowded, and there are plenty of areas where families can spread out without feeling like they’re taking over the space.

The beach is another huge advantage. The calm water makes it easy for kids to swim, paddle, and snorkel, and there are enough activities nearby that families can easily spend an entire day without needing to leave the resort.

The Francis H. I’i Brown Club

If there’s one upgrade I think many families should seriously consider, it’s access to the Francis H. I’i Brown Club.

I’ve stayed in plenty of club-level accommodations over the years, and this is one of the best values I’ve encountered.

Club guests have access to a dedicated lounge and private breakfast area that feels much calmer than the main restaurant. Throughout the day, there are snacks available, along with a refrigerated drawer stocked with sandwiches and grab-and-go items whenever hunger strikes. For families, this can be incredibly convenient.

There is also a candy room, ice cream, drinks, afternoon snacks, and dedicated staff whose entire job is to make sure club guests have everything they need.

What impressed me most was how personalized the service felt. My son has food allergies, and the team consistently went out of their way to make allergy-friendly options for him so he never felt left out.

The club also comes with some surprisingly valuable perks outside the lounge itself.

Guests receive priority beach and pool seating, with the best locations reserved specifically for club members. Everything is handled through text, making the process incredibly easy.

There’s also complimentary access to a Mercedes through the resort’s Drive Program. Club guests can reserve a vehicle for up to three hours at a time, which is perfect for exploring nearby beaches, grabbing lunch outside the resort, or running errands without needing a rental car.

It’s one of those benefits that sounds small until you actually use it.

The Rooms and Residences

The standard rooms are beautifully designed and feel bright, modern, and spacious.

For families, however, I think the residences are where Mauna Lani really shines.

Compared to many luxury resorts in Hawaii, the multi-bedroom residences offer exceptional value. Families gain significantly more space, full kitchens, laundry facilities, multiple bedrooms, and private outdoor areas while often paying less than they would for multiple hotel rooms.

Some residences even include private pools, which can be everything when traveling with children or extended family and juggling nap times.

For grandparents traveling together with children and grandchildren, I often think these residences make more sense than booking multiple connecting rooms.

Is Mauna Lani Worth It?

If you’re looking for the most ultra-exclusive experience on the island, you may find yourself comparing Mauna Lani to Four Seasons Hualalai or Kona Village, and I think all of them are great in their own right.

What keeps bringing me back to Mauna Lani is that it delivers so much of what families actually need.

The beach is easy and swimmable. The snorkeling is excellent. The residences offer fantastic value. The staff are wonderful with children. The Francis Brown Club adds meaningful perks rather than gimmicks. And the overall atmosphere feels relaxed in a way that encourages everyone to settle in and enjoy themselves.

For families visiting the Big Island, especially those traveling with younger children, I think Mauna Lani remains one of the easiest luxury resorts to recommend.

This post was brought to you in collaboration with Mauna Lani, all opinions on our stay are my own.

After several days here with my family, what stood out most wasn’t a particular restaurant, activity, or room feature. It was how peaceful the entire resort felt. Even when occupancy is high, Kona Village never seems crowded, and that sense of space ended up being one of our favorite things about staying here, as crowds have been one of our biggest issues at other five star resorts in Hawaii.

Every hale here stands alone, and with only 150 of them, you’ll never be fighting for a beach or pool chair. Plus, it was so family friendly while still being refined and elegant. Here’s everything to know before you book Kona Village:

How to Book with Free Breakfast and Other Perks

As a Rosewood Elite partner, we can add complimentary perks to your stay at no additional cost, including:

• Upgrade on arrival, subject to availability.
• Daily breakfast credit of $120 per room.
• $150 USD Resort or Hotel credit to be utilized during stay.
• Early Check-In / Late Check-Out, subject to availability.
• Free nights that aren’t always publicly offered

Since we specialize in luxury family travel, we’re also happy to help you compare Kona Village to other Big Island resorts and determine which room category makes the most sense for your family.

A Brief History

The original Kona Village opened in the 1960s and became one of Hawaii’s most beloved resorts thanks to its laid-back atmosphere and traditional hale accommodations. After being severely damaged by the 2011 tsunami, the resort remained closed for more than a decade before reopening as a Rosewood property in 2023.

Thankfully, much of what made Kona Village special was preserved. Instead of hotel towers, guests still stay in standalone hales spread throughout the property, giving the resort a much more spacious feel than many luxury resorts in Hawaii.

What Makes Kona Village Special

While many luxury resorts on the Big Island are centered around a main building, Kona Village feels more like a small community spread across the coastline. The property covers 81 acres, and because everything is spread out, you never feel like you’re sharing the resort with hundreds of other guests.

There are fishponds, walking paths, beaches, lava fields, and palm groves woven throughout the property, and we found ourselves biking all around discovering hidden little beaches and new corners of the resort simply because it was such a beautiful place to wander. If you’re looking for a resort with a lively atmosphere and lots of action, Kona Village may feel too quiet. If you’re looking for a place where everyone can slow down a bit, it’s hard to beat.

Personally, I go to Hawaii to relax. It grinds my gears when there’s a queue at 7am to put a towel down on a lounger and the battle for space wages all day (and yes unfortunately this DOES happen at five star resorts – looking at you Four Seasons Maui, even though I genuinely loved everything else about you).

Plus, Kona is one of the driest parts of Hawaii, so the weather is more on your side!

Why Families Will Love It

One thing I appreciated about Kona Village is that it manages to feel luxurious without feeling like children are an afterthought. Families are everywhere, but the resort never feels chaotic.

Kids under four eat free throughout the resort, which can add up to significant savings over the course of a stay. There is also a kids club for children ages five and up, along with daily activities that go beyond the typical coloring pages and movie room setup you find at many resorts.

During our stay there were movie nights on the lawn, lei making, pond fishing, lawn games, and shave ice at the pool made with real fruit juice. What I liked most was that many of the activities encouraged kids to spend time outdoors and engage with Hawaiian culture rather than simply being entertained.

The size of the property is also a huge advantage for families. There are so many places to explore that my son was constantly finding something new to look at, whether it was the fishponds, tide pools, or simply riding around the resort. Since restaurants are beachfront and they have plenty of sand toys, he was able to play at dinnertime too while we waited for our food to arrive.

The Rooms

Like the original Kona Village, accommodations are housed in standalone hales rather than hotel buildings. This gives every room a sense of privacy that’s difficult to find at most resorts.

We loved being able to step outside and immediately feel immersed in the landscape rather than walking down a hallway and waiting for an elevator. The rooms themselves feel fresh and modern while still incorporating Hawaiian design elements, and the indoor-outdoor feel works especially well in this climate.

For larger families, Kona Village also offers several four-bedroom villas that come with dedicated butler service. These are among the most impressive family accommodations on the island and work particularly well for multigenerational trips.

Getting Around the Resort

One of the things that makes Kona Village unique is that many guests get around by bicycle. Since the property is so large, biking is often faster than walking, and it adds to the relaxed atmosphere of the resort.

Adult bikes are provided, and families don’t have to miss out. The resort also offers children’s bikes with training wheels as well as child seats that can be attached to adult bikes for younger kids. Riding around the property quickly became one of our favorite parts of the stay and made exploring feel like an activity in itself.

The Pools

The main pool strikes a nice balance between family-friendly and relaxing. We never felt like we were fighting for chairs or competing for space, which is something I can’t say about every luxury resort in Hawaii.

Poolside service was attentive without being intrusive, and the daily popsicles and biweekly shave ice was a huge hit with both kids and adults. Because the resort attracts a mix of families and couples, the atmosphere remains calm even during busy periods as there’s a dedicated adults only pool and multiple beaches.

The Beach and Snorkeling

While many Big Island beaches can be rough or difficult to access, the beach at Kona Village ended up being one of our favorite parts of the property.

The protected bay creates calm conditions much of the time, making it a great place for families to swim, paddle, or simply relax. We were also impressed by the snorkeling. The reef just offshore is full of marine life, and we spotted colorful fish almost immediately after entering the water.

Included in the daily resort fee is access to activities like a sunrise outrigger canoe paddle and paddleboards, kayaks, and snorkel equipment.

Is Kona Village Worth It?

For families looking for waterslides, nonstop activities, and a high-energy atmosphere, there are probably better choices on Maui or Kauai.

For families looking for space, excellent snorkeling, thoughtful kids programming, beautiful accommodations, and a resort that feels genuinely relaxing, Kona Village is one of the best we’ve experienced in Hawaii. What we’ll remember most isn’t any one activity or meal, but how easy it was to settle into the rhythm of the resort and simply enjoy being there together. Get in touch to book with complimentary VIP perks.

After being pickpocketed in Europe years ago, I pay more attention to these features than I otherwise would. What shocked me most about that experience was how unbelievably fast it happened. I always assumed I’d notice if someone was getting into my bag, especially since I travel so much and tend to be pretty aware of my surroundings, but it literally took place in a matter of seconds and I didn’t feel a thing.

Most theft abroad isn’t dramatic. It’s in crowded metros, airports, tourist sites, or someone brushing past you for half a second, and that’s all it takes.

Rachel Bloom bags are clearly designed with that kind of real-world travel in mind, but unlike most security-focused bags, they still look elevated and stylish enough that I actually want to use it! So is it worth the price tag? Here’s my full review:

TL;DR – I tested this bag out as part of a sponsored IG story and knew I had to write this review (which isn’t sponsored) because the bag is that good. It truly can’t be opened without YOUR fingerprint. Get it – the quality is great and it’s cute, too.

The Fingerprint Lock Is KEY

The feature Rachel Bloom is best known for is the fingerprint locking system, and THIS is what separates these bags from every other anti-theft bag I’ve seen.

Instead of relying on little clips or zipper locks, the main compartment stays locked until you unlock it with your fingerprint. If someone can’t physically open the bag, they can’t quickly slip a hand inside in a crowded place.

That’s also why this feature immediately made sense to me after my own experience being pickpocketed. The theft itself was so fast and subtle that a lock that can only be opened with your own hand would have made it impossible.

The bags can store multiple fingerprints as well, which is useful if you’re traveling with a partner or family member who may also need access. I chose to do a finger and thumb on both hands as well to make it easier for me to open it quickly.

They Don’t Scream “Tourist”

Most anti-theft bags immediately look overly utilitarian or tactical, which ironically can make you stand out even more while traveling. Rachel Bloom bags still look like luxury handbags first. The leather, hardware, and overall design feel polished and modern and like something I actually want to use daily.

I also appreciate that the collection includes different silhouettes depending on how you travel. There are totes, backpacks, crossbodies, belt bags, and mini backpacks, so it doesn’t feel like a one-size-fits-all approach.

I have the backpack, which works well since I travel with so much tech gear, but I’d be interested in getting the cross-body too for the days I’m out sightseeing and want my wallet and phone protected.

GPS Tracking Adds Another Layer of Security

One of the other standout features is the built-in GPS tracking through the Rachel Bloom app.

You can track your bag’s location, receive distance alerts if it gets too far away from you, and even remotely activate alarms or unlock the bag through the app. It’s basically integrating some of the functionality people already use AirTags for directly into the bag itself.

For frequent travelers, I can honestly see this being incredibly useful. Airports, lounges, trains, cafés, hotel lobbies — there are so many moments while traveling where bags temporarily leave your direct line of sight.

I also think this feature would be especially appealing for solo travelers who want a little extra peace of mind while navigating busy destinations.

Slash-Resistant Materials Are One of Those Features You Hope You Never Need

Before I started traveling extensively, I didn’t even realize slash-and-run theft was a thing in some destinations. Apparently it’s common enough that many anti-theft travel brands now reinforce their straps and bag linings with cut-resistant materials.

Rachel Bloom does this underneath the leather exterior so the bags still maintain a luxury look rather than looking bulky or technical.

It’s one of those invisible features that hopefully never matters, but if it does, it matters a lot.

Nice Organizational Features

The backpack has a sleeve to easily slide over a suitcase handle, and the straps are adjustable with a belt-style, classy, golden clasp.

Inside, there are plenty of pockets for organization, and a dedicated pocket just for the GPS tracker.

The Downsides

The biggest downside is definitely the price point, but when compared with most travel backpacks, it’s not actually all that much more. Plus, the materials and fingerprint reader are premium features.

You’re paying for premium leather, integrated technology, security features, and design rather than just basic storage.

I also think it depends on how often and where you travel. In Europe, it’s SO common to get pickpocketed, having something like this is huge. For people constantly moving through airports, cities, trains, and crowded tourist destinations, I can absolutely see the need.

There’s also the reality that smart bags require charging, and no tech product is completely perfect all the time. Bluetooth occasionally disconnects and you’ll need to periodically recharge the bag.

Final Thoughts

What I like most about Rachel Bloom is that they seem to understand that women don’t actually want to carry something that looks aggressively “safe.” We still want a beautiful bag that works with the rest of our wardrobe and doesn’t instantly label us as tourists.

The fingerprint lock, GPS tracking, slash-resistant construction, and app integration all feel thoughtfully designed around the kinds of situations that actually happen while traveling, especially in crowded destinations where theft tends to happen quietly and quickly.

After my own experience being pickpocketed without even realizing it until afterward, I definitely understand the appeal of having an extra layer of protection built into something you already carry every day.

*Some links in this post are affiliate links that support us at no extra cost to you when you purchase through them. We only recommend products we love and use ourselves. Your trust always comes first!

I’ve tested every single one on this list myself, in many cases, for a decade or more. These are the best travel backpacks out there for women:

• Best Luxury anti-theft: Rachel Bloom
• Most convenient pockets: Pakt Travel Backpack
• Smartest: Nordace Siena
• Sturdiest: Baggallini
• Best anti-theft: Pacsafe X Travel Safe
• Best for carry-on only travel: REI Co-op Ruckpack 40L
• Most stylish: Monos
• Best for outdoors: Deuter Aircontact 45+10
• Best waterproof: Exped Typhoon

1. Pakt Travel Backpack

I’ve been using the Pakt Travel Backpack for nearly four years now, yet it still looks like the day I got it. I initially received this backpack as part of a social media project, but it quickly became my ride or die carry on for all of my electronics.

The main reason is how easy it is to access the pockets, particularly for one’s laptop while in airport security. You can unzip the entire thing like a suitcase, or just unzip the top for quick access to the laptop sleeve. Security-wise, though the zippers don’t lock, the laptop is in the middle of the bag and would be hard to swipe. There are also hidden pockets going in just about every direction, and it makes organization for disorganized people (like me) simple. There’s an all-important waist strap, and thick backpack straps, which helps it stay comfortable despite how heavy mine always is.

It’s not the prettiest on this list, but it’s the one I reach for almost every time for how sturdy and easy it is to use. Read my full Pakt travel backpack review for more info.

2. Rachel Bloom

Rachel Bloom bags are some of the most stylish anti-theft travel bags I’ve come across, which is saying a lot because most security-focused bags tend to sacrifice aesthetics completely. This is the only bag I know of that requires your finger print to open!

The backpack styles in particular still feel polished and elevated rather than overly tactical, with clean leather designs that work just as well for a city trip as they do for the airport. Features like fingerprint locks, GPS tracking, slash-resistant materials, RFID protection, and app-based alerts are all built directly into the bags, AND they look so stylish, it could easily be an everyday bag. We love an option that doesn’t scream ‘tourist’.

After being pickpocketed in Europe years ago without even feeling it happen, I’ve become a lot more aware of how quickly theft can happen while traveling, especially in crowded cities, train stations, and airports. If you want a travel backpack with an extra layer of security that still looks chic enough for everyday use, these are definitely worth considering. Get it here.

Read my full Rachel Bloom review.

3. Baggallini

The Pakt is more what I would call a masculine looking bag, though it fits the female frame well. But if you’re looking for something a bit more stylish, Baggallini’s bags have a bunch of features and stand the test of time. Each ‘bagg’ has RFID blocking pockets, they’re made from lightweight nylon material, many of them, including this backpack, are expandable, and when I shared about bringing them on our winter Japan trip on my Instagram, I got so many DMs and comments from Baggallini lovers saying theirs had lasted for years. I’ve been using mine for about a year, and it’s great. It’s also reasonably priced at $130.

They don’t have as much structure as some of the other bags on this list, so if you’re looking for something to hold delicate items like electronics, it’s probably not ideal, but it would work well for a laptop or tablet and a single camera, among other important carry-on items. Read my full Baggallini review for more on all of their bags.

4. REI Co-op Ruckpack 40 Pack

I bought this bag back in 2012 when I was about to embark on my big solo trip to Thailand, which was the start of this entire blog. I traveled carry-on only with this backpack for over a year, and have used it extensively since, and not a single part of it has broken. This thing is truly a tank.

The only downside is my laptop would be in the water bladder sleeve in the inside of the bag, which meant I had to dig in order to get it out in security lines. Still, this backpack is over a decade old and still kicking! It doesn’t have all the pockets and features of the Pakt or the style of the Monos (later on this list) or Baggallini, but it got me through a full year of being a nomad without even flinching. It also works well for hiking shorter trails as a hiking backpack. At $169, I’m of the opinion that it’s a steal.

5. Nordace Seina

The Nordace Siena is a ‘smart backpack’ with the ability to charge your electronics with the built-in USB charger, along with a water-resistant exterior to keep your belongings dry in unpredictable weather.

The ergonomic design and padded straps make it super comfortable to wear for long periods, whether you’re hiking through the airport or strolling through city streets. And priced competitively (at $109), it’s a smart investment for those who need to stay charged and connected when they travel. It also looks super classy and comes in a wide range of colors from classic red or black to pink, aqua, and dark green. Read our full Nordace Siena review for more.

I’ve also done a full comparison of Pacsafe vs. Nordace.

6. Pacsafe X Anti Theft 20 Backpack

Back when I first started traveling in 2012, I bought Pacsafe all the things. I was even a brand ambassador with them for a few years since I was so passionate about the products. When staying in hostels, there’s nothing that gave me better peace of mind than using their bag locker, and I loved that the zippers could all be hooked and hidden on the backpacks. The 20L anti theft backpack was the most useful for me as a carry-on, and features RFID blocking technology as well as anti-slash material, hidden pockets, and zipper hooks that make a quick pick-pocketing impossible. For those traveling in Europe, particularly in Spain or Italy, this is a must.

They also make many sizes, including a 55L backpack I still love and use, and crossbody bags with the same anti-theft technology.

7. Monos Metro Backpack

Easily the most stylish on this list, the Monos Metro Backpack and Duffel comes in a wide variety of colors, including bright yellow, sage green, and purple, in addition to the usual suspects like black and beige.

It features a minimalist exterior with clean lines and a durable water-resistant shell, perfect for both urban explorations and as a flight carry on.

Inside, you’ll find a surprisingly spacious main compartment with a padded laptop sleeve as well as detachable front pouch with a whole organization system. From a quick-access front pocket for your phone and wallet to interior pockets for smaller items like keys and chargers, everything has its utility.

It also pairs perfectly with Monos luggage, sliding onto the handle with ease. I love this combo for when I want to arrive looking chic.

8. Exped Typhoon

I switched to the Exped Typhoon for a while when I was doing more hiking and backpacking, especially if it was a day hike where I might experience rain (hello, Patagonia!), it also gave me more peace of mind when traveling on smaller boats in Indonesia where your bag is basically just resting on top of the deck getting splashed. If you truly want your stuff to be in a bag that’s not just ‘water resistant’ but fully waterproof when properly rolled and sealed, this is the one.

I would probably have used it forever, but I started to worry about my electronics getting jostled since there’s really no insulation or padding. It also lacks any kind of pockets or organization system, so I’d have to just stack things in there. That said, I really appreciated it truly kept things dry. It comes in many sizes as well from 15 to 30 liters.

9. Osprey Fairview 40 Women’s Travel Backpack:

Now, let’s talk about the Osprey Fairview 40 Women’s Travel Backpack. As a female traveler, finding a backpack that fits just right can be a challenge, but Osprey has nailed it with this one. It’s also front-load and looks a little more stylish than the REI.

The women-specific design means it contours to my body comfortably, even when fully loaded. It’s got all the features I need for long-term travel, including a stowaway harness and detachable daypack. And at a mid-range price point, it’s a solid investment for that lasts. We love their hiking backpack carrier as well now that we have a toddler.

10. Deuter Aircontact Core 45+10 Backpack:

If you’re planning an extended backpacking trip, the Deuter Aircontact Backpack is worth considering. With its generous capacity and adjustable suspension system, it’s designed to comfortably carry heavy loads for days on end.

The ventilated back panel keeps you cool and dry, even in hot and humid climates, while the integrated rain cover ensures your gear stays dry in wet weather. And while it’s on the higher end ($230) in terms of pricing, the durability and performance make it a worthwhile investment for serious travelers and hikers alike. I just might have to give our Deuter backpack carrier the edge over the Osprey!

My Favorite Travel Backpack

Right now, the bag I’m still loyal to is the Pakt. It’s been my main bag for over four years. It may be one of the pricier bags on this list, but there’s a reason it goes out of stock so often – people love how well this bag holds up and how intelligently it’s designed. After all the punishment I’ve put it through, it doesn’t show any signs of wear.

My second place is the Rachel Bloom. It’s not every day that you come across a backpack that’s this chic and can’t be opened without a fingerprint! It’s not able to handle ALL of my tech gear, but for trips where I don’t have all of my cameras and lenses with me, I love the look and peace of mind of this one.

*Some links in this post are affiliate links that support us at no extra cost to you when you purchase through them. We only recommend products we love and use ourselves. Your trust always comes first!

Tucked into the Sonoran Desert just outside Tucson, the setting alone is enough to reset your nervous system. The mountains glow pink at sunset, the air is dry and warm, and everything about the property feels intentionally quiet.

Miraval is part of the Hyatt portfolio, and it’s one of the places where Hyatt points can unlock an experience that would otherwise be quite expensive.

In my case, I booked the stay using a combination of Hyatt points and a Hyatt Privé rate — which ended up working out perfectly.

What Makes Miraval Different

Miraval isn’t a typical luxury resort where the goal is to lounge by the pool all day, though there are beautiful pools if that’s what you want.

Instead, the experience revolves around activities, wellness programming, and time spent outdoors.

Each day you can choose from dozens of options, like:

• Yoga and meditation classes
• Guided hikes in the desert
• Sound healing sessions
• Equine therapy experiences
• Fitness classes and workshops
• Culinary demonstrations

Some activities are included, while others require additional credits or fees. The schedule is packed enough that you could easily fill every hour of the day if you wanted to.

But you don’t have to.

One of the things I appreciated most about Miraval is that it doesn’t pressure you into being constantly productive about your wellness. Some guests are running from class to class. Others are reading by the pool all afternoon. Both approaches fit perfectly.

Rooms and the Upgrade I Received

Miraval accommodations are designed to be peaceful and understated rather than flashy.

When I booked my stay, I used a combination of Hyatt points and a Hyatt Privé rate, which is a partner program Hyatt offers through select travel advisors (if you’re interested in a Hyatt Prive, booking, get in touch as I’m an advisor).

Even though the stay involved points, the Privé booking still allowed the hotel to prioritize my reservation for upgrades, and I ended up receiving a really lovely room upgrade upon arrival.

That said, I wish I’d opted for a room with a mountain view. I went for the lowest category and I think an upgrade from a mountain view room to a suite would have been even more amazing.

The Setting: The Sonoran Desert at Its Best

The property sits in a beautiful stretch of the Sonoran Desert with the Santa Catalina Mountains rising behind it just outside of Tucson, right at the bottom of Arizona, meaning winters are mild and summers are HOT. I visited in February and though there was some desert rain, it didn’t bother me at all and added to the coziness of the experience.

This landscape has a very specific energy. It’s quiet, open, and full of subtle colors — soft greens from the cacti, deep rust tones in the rocks, and golden light that seems to last forever in the evenings.

Sunrise hikes quickly became one of my favorite parts of the stay. Watching the desert slowly wake up while the mountains catch the first light is one of those simple experiences that feels grounding.

The Food (Which Is Surprisingly Good)

One concern people sometimes have about wellness resorts is the food.

You imagine tiny portions of quinoa and kale.

Miraval does focus on nutritious, balanced meals, but the food here is varied and although the breakfast and lunch were fine – nothing out of this world – the dinners were truly delicious.

The approach is more about thoughtful ingredients and balanced cooking rather than strict dieting.

It never felt restrictive.

The Spa and Wellness Experiences

The Life in Balance Spa is one of the highlights of the property.

Like the rest of Miraval, it’s designed around calm spaces and desert views. There are indoor and outdoor relaxation areas, quiet pools, steam rooms, and a long list of treatments inspired by different wellness traditions.

If you plan to book treatments, it’s worth scheduling them in advance since they fill up quickly.

Even if you skip treatments, the spa facilities alone are worth spending time in as they’re open to anyone staying there. Each night before bed, I did at least an hour of sauna, steam, cold plunge, stargazing, hot tub, repeat.

Booking Miraval with Hyatt Points

Miraval is one of the Hyatt properties where using points can offer really strong value.

Award stays typically include:

• accommodations
• all meals
• select wellness activities
• access to the spa facilities

Given how much programming and dining is included, redeeming points here can feel much more valuable than using them at a typical city hotel.

In my case, pairing the points booking with a Hyatt Privé rate helped maximize the overall experience, especially when it came to the room upgrade.

Is Miraval Arizona Worth It?

If you’re looking for a traditional luxury resort with nightlife and beach clubs, this probably isn’t the right fit.

But if you want a place that genuinely helps you unplug — somewhere you can move your body, learn something new, spend time outside, and leave feeling reset — Miraval does that incredibly well.

It’s not about escaping life completely.

It’s more about stepping out of the noise long enough to remember what it feels like to be present.

And the Sonoran Desert turns out to be a pretty perfect place to do that. Get in touch to book.

Hyatt Privé is one of those things that sounds mysterious and slightly exclusive, which usually makes people assume it’s complicated or expensive. It’s neither. It’s simply Hyatt’s preferred partner program for select travel advisors, and it unlocks additional benefits at many of Hyatt’s top properties.

The most important part — and the thing almost nobody explains clearly — is this:

It is still a direct booking with Hyatt.

You’re not booking through a third-party site. You’re not giving up your points. You’re not losing elite benefits. When is it worth booking? Let’s dive in.

TL;DR: Here’s how to get access to these rates – Contact me, I’m a Hyatt Prive advisor, and I don’t charge any fees.

What Benefits Does Hyatt Privé Include?

Benefits vary slightly by property, but typically include:

• Daily full breakfast for two
• A $100+ property credit (often food & beverage or spa)
• Priority for room upgrades
• Early check-in when available
• Late check-out when available
• A welcome amenity

To put that into perspective, breakfast at many Park Hyatt or Andaz properties can easily cost $50–$70 per person per day. Over a three-night stay, that alone could be $300–$400 in value, before you even use the property credit.

And that’s without factoring in a potential upgrade.

How Does Hyatt Privé Work?

Hyatt Privé is an invitation-only partner program between Hyatt and select travel advisors. It applies to participating luxury brands within Hyatt’s portfolio, including:

• Park Hyatt
• Alila
• Andaz
• Miraval
• Grand Hyatt (select properties)
• Thompson (select properties)

You can simply reach out to an advisor who is part of the program, let them know the hotel and dates and room type, and see what the Prive rates are for your stay.

Sometimes the rate is the same as the best available rate, sometimes it’s slightly higher but still worth it, and sometimes it won’t make sense.

The process is, you’ll get the rates, give the agent your billing info, and they will make the booking via the Hyatt Prive advisor portal.

You still earn World of Hyatt points.
You still receive elite night credit.
Your reservation still appears in your Hyatt account.

The booking is held directly with the hotel.

The only difference is that you receive additional perks attached to your stay.

Is Hyatt Privé More Expensive?

It depends.

Hyatt Privé for some resorts will be the same best rate you’re seeing on the Hyatt website. For others, it may run higher but the perks may outweigh the extra cost (which is usually not more than a few percentage points more).

If you’re comparing flexible vs. flexible, the cost is the same. The difference is that Privé adds perks.

Most travelers booking luxury hotels are already choosing flexible rates for peace of mind. In that case, Privé is essentially added value at the same price.

Is This Really Still a Direct Booking?

Yes.

This is where confusion tends to happen.

When a Hyatt Privé reservation is made:

• It is confirmed directly with Hyatt
• It shows up in your World of Hyatt account
• You earn points
• You receive elite status benefits
• You can manage the booking through Hyatt

It is not an online travel agency booking.

You are not giving up control of your reservation.

You’re simply adding a partner layer to it.

Can I Combine with Hyatt Points?

Unfortunately, when booking with points, you’re not able to stack agent benefits on top.

However, if you’re only booking some nights on points and planning the rest with cash then, yes, you can book the stays separately then we can help you link them with the hotel. It’s best to book the same room type so you’re not having to switch partway through.

How to Book Hyatt Privé

If you’re considering a stay at a participating Hyatt property, the process is simple.

You share your dates and the hotel you’re considering. We confirm eligibility, verify the applicable perks for your stay, and provide the rate — which will match the standard flexible rate publicly available.

There’s no membership to join and no separate enrollment required.

Just the same booking, done a little smarter.

If you already have an existing booking, we may still be able to help.

Hyatt Privé isn’t a loophole or a hack. It’s simply a partner program most travelers don’t know about.

If you’re already booking luxury Hyatt properties, it’s worth checking whether your stay qualifies.

Because if you’re paying the same rate anyway, you might as well have breakfast covered.

I read forums and tried to get a sense of which was better before we went, but I couldn’t decide, so we spent three nights at each one this month.

If you’re choosing between them, here’s the stuff that actually affects your days, your meals, your kid’s mood, and whether you feel like you’re on a retreat or on a classic resort vacation.

The vibe: secluded and peaceful vs. classic resort energy

Montage Kapalua Bay (pictured above) felt almost like it was hiding. Part of that is the location — Kapalua feels quieter, more tucked away, and there aren’t big resorts stacked right next door. Add the fact that Montage is only around 70 residences, and it just naturally feels more peaceful. Less foot traffic, less noise, fewer “events,” more exhale.

Four Seasons Maui is more of that iconic Maui resort experience. You’re in Wailea, which is well-connected and walkable in that “resort-to-resort” way. There’s a little more buzz. Not spring break chaos — just more going on around you. If you like feeling like you’re in the center of things (without it being overwhelming), with easy access to shopping, golf, and a wealth of restaurants, Wailea delivers.

Beach: snorkeling paradise vs. gentle waves you can actually play in

This was the biggest functional difference for us.

Montage / Kapalua Bay is an amazing snorkeling beach. It’s calm, clear, there are lots of turtles, and it’s the kind of water that makes you want to grab a mask and stay out there. But it’s not really the beach I’d pick if the goal is chasing waves or boogie boarding. It’s more “float, snorkel, spot turtles” than “run, jump, ride.” It was perfect for us as we took turns snorkeling and playing in the gentle waves with our toddler. We also saw tons of whale spouts – dozens per day – and had gorgeous views of Lanai and Molokai in the distance, and a full-on sunset view.

Four Seasons / Wailea had crystal clear water and slightly bigger waves — still gentle, but enough to make it fun. Our three-year-old was old enough to go past the small break with us, and it felt like the perfect setup for boogie boarding as kids get a bit bigger. We saw turtles here too, though far fewer, and whales in the distance, but the main draw was simply how good the water felt for actual play. You can catch the sunset from the beach, though it’s a bit angled.

Food: cook-at-home flexibility vs. lots of choices and zero effort (but more cost)

This is perhaps the biggest difference between the two resorts, along with the amount of space you get at the Montage vs. Four Seasons:

Montage is set up for people who are happy cooking sometimes. Every residence has a full kitchen (ours even had a wine fridge, real oven, full fridge, etc.), and honestly that’s part of the point. The tradeoff is that onsite dinner options are limited — think one main dinner restaurant plus in-room dining. It’s not a “pick between four restaurants tonight” kind of resort.

Four Seasons is the opposite experience: more restaurant choices (they have four onsite restaurants), and you can’t cook unless even if you want to as they don’t have kitchens or residences. Being based in Wailea makes it easy to switch things up — you’re near other resorts, so you can wander for a different meal or vibe without it becoming a whole mission.

They have an incredible breakfast buffet, though. Just make sure you book through a Four Seasons Preferred Provider so that it’s included in your stay ($120 daily value!).

Booking with us: perks at no extra cost

If you’re booking either of these, it’s worth doing it with the extra perks through a luxury travel advisor — especially because it doesn’t raise your rate and, at least in our case, we don’t charge any fees.

Montage Kapalua Bay (Virtuoso perks)

• Priority for a room upgrade on arrival, when available
• Daily $45 breakfast credit for two per bedroom
• $150 resort or spa credit per stay
• Early check-in and/or late check-out, when available
• Preferences communicated to the hotel ahead of arrival

Contact us or browse here (desktop only to pull rates).

Four Seasons Resort Maui at Wailea (Four Seasons Preferred Partner perks)

• Daily breakfast for two per bedroom ($120 daily value + kids under 5 eat free)
• $100+ Resort credit per stay (amount varies by season)
• Priority for room upgrades, when available
• Early check-in and/or late check-out, when available
• Preferences shared directly with the resort before arrival

Contact us to book.

Rooms and layouts: bigger group friendly vs. classic suite convenience

Montage is a dream for bigger groups because it’s all residences, and they go up to multi-bedroom villas (up to four bedrooms). You get real separation, multiple bedrooms, in-unit laundry, full kitchens, multiple dining areas, grills, in our case 4 bathrooms for our 3-bedroom residence, big lanais… the whole “everyone can be together without being on top of each other” thing.

Four Seasons still worked great for us as a family because of our suite setup — we had an executive suite with a closing door and a pull-out couch, which made evenings and early bedtimes way easier. But this is a room that normally goes for $3500/night, which would be more affordable if booking Montage, and with more space. If you’re traveling with another family, grandparents, or a full crew and want everyone under one roof, Montage has the advantage.

Pools: quiet corners vs. classic resort comfort

Both resorts have surprisingly similar waterslides in terms of size — small, approachable, and perfect for younger kids rather than thrill-seeking teens. The difference is really in how the pool experience feels once you’re there.

At Montage Kapalua Bay, the pool is honestly one of the best we’ve seen anywhere. It was recently revamped, and it shows. The layout is layered and expansive, with multiple levels, tucked-away sections, and little nooks that make it easy to feel like you’ve carved out your own space. Even when other families were around, it rarely felt crowded. You could settle into one corner and almost forget there was anyone else there.

The Four Seasons Maui pool experience feels more traditional – but not in a bad way. It’s polished, social, and very comfortable. One thing we really appreciated was that there are cabanas available that you don’t have to pay extra for, which isn’t always the case at resorts at this level – though they will fill up with people arriving at 7am to snag a spot. While we never made it in time for the prime locations, we were always able to find something. It made it easier to post up for the afternoon without feeling like you had to strategize or commit to a spend. The service was very attentive, which is what FS is known for.

If you love finding a quiet pocket and staying put for hours, Montage’s pool wins. If you like a classic resort pool setup with easy comfort and thoughtful touches like included cabanas, Four Seasons does it really well.

Service: both great, but Four Seasons does that Four Seasons thing

The service at both was excellent. You’ll truly want for nothing at either spot.

Montage felt warm and calm and attentive — and the twice-daily housekeeping in a full residence was honestly kind of wild (they even did the dishes we left in the sink). They even brought a full cake for my partner’s birthday, and left such thoughtful touches in the room for our toddler as well. They’re partnered with UPPAbaby, so they have strollers and cribs onsite of the highest quality.

And Four Seasons is legendary for a reason. It had that signature smoothness where everything is immaculate, everything runs on time, and you’re never thinking about logistics because someone already handled it. Housekeeping knew our names. Valet was genuinely helpful when we were figuring out where to go for the day. It’s what Four Seasons is known for across properties — that quiet competence that makes you feel like you can actually relax.

Also: Four Seasons has a free photo service that I wish more resorts did. It’s a quick ~10-minute session where a photographer takes photos using your phone, so you get them immediately without a gallery, waiting, or awkward upsell.

So… which one wins?

It depends on what kind of trip you’re trying to have. Here’s how I’d call it.

Pick Montage Kapalua Bay (full review here) if you want:

• Maximum peace and quiet
• A secluded part of Maui without big resorts right next door
• A snorkeling-first beach (turtles, calm water)
• A place that works beautifully for bigger groups (multi-bedroom residences)
• The option to cook and spread out like you actually live there

While this is very much a 5-star luxury resort, the value/amount of space you get for your money at Montage will be higher. For the price of an executive suite at the Four Seasons, you can get a 2-3-bedroom villa at the Montage with a full kitchen and beautiful view.

Contact us or browse here (desktop only to pull rates).

Pick Four Seasons Maui at Wailea (full review here) if you want:

• A beach where you can play in gentle waves (and boogie board as kids get bigger)
• More restaurant choices and zero desire to cook
• The convenience of Wailea (walkable resort area, near golf courses, easy to hop around)
• A location that’s closer to the airport
• That signature Four Seasons service — names remembered, everything seamless — plus the free sunset photo session on your phone

Contact us to book.

If I had to sum it up in one line: Montage is the calm, residential reset. Four Seasons is the classic Maui resort vacation with legendary service and easier food variety.