“One of the reasons we keep this tradition going is that we’ve learned that our kids, who range in age from 55 to 64, are such a treat to share destinations and experiences with,” Trish says. “And yet it’s a very different experience, even on a familiar ship, from our usual travel as a couple. On those trips, we’re more likely to seek out other guests and participate in more onboard activities. Here the focus is family.”

The biggest difference this time around? “I certainly put more work into the pre- and post-cruise planning,” she says.

The Harwoods are hardly alone in prioritizing trips with their adult kids and, down the road, a post-graduation trip with a grandchild, is already on the horizon. Multi-generational travel is having a moment: in the 2026 Virtuoso Luxe Report, the two strongest motivations to travel were spending time with immediate family and going on multigenerational trips.

It’s easy to see why cruising is such a natural fit for family travel, Trish adds. “Once you’ve identified your ship and itinerary, the heavy lifting is already handled. There’s no worrying about dinner reservations or where you’re going to stay, and the ship’s shore excursion department handles activities in port.”

This is the fifth trip the Harwoods have planned with one or both of their sons, and Trish has picked up plenty of wisdom along the way. Her first rule: “We’re talking vacations, not family reunions, which have different needs and protocols. These are trips with our adult children, not kids — and they’re our guests.”

Here are her top tips for planning a multi-generational cruise of your own:

Trip planning

• Start with a low-pressure suggestion: “We’re going to the Caribbean — would you be interested in joining as our guests?” Or “we’re thinking of visiting the Baltic; is this something you’d be interested in?”
• Be clear about financials from the start — who’s paying for what? Major expenses include airfare, the cruise itself, pre- and post-cruise transfers, and accommodations and meals on land.
• Air travel can be the trickiest piece, especially with limited seats and choices lately. I coordinate with the family and usually book everyone’s flights. But on one trip a couple couldn’t decide when to fly and it became frustrating. I finally said, “Here’s what our flights cost.  I’ll send that amount to your bank account and you decide how to get there and book it yourself. 
• Whichever approach you take, make sure everyone is treated equally. If one couple can’t join a trip, we make sure a similar trip is offered another time.
• Think carefully about timing. In our family, one couple is retired, and one still works — how much vacation time does the working couple have? If it’s limited, they might only join for part of the trip. Is the destination “good” (weather, crowds, etc.) during the window your kids can get away? If not, are you willing to adjust your own plans?

Setting expectations

• Talk through goals and expectations before you leave. What do you, as host, expect? What do your kids — or teenage grandkids — want from the trip? The couple still working will likely be exhausted just getting to the airport on day one, while the retired among you can’t wait to start sightseeing.
• This goes beyond schedules, too. On a trip to London, your teenage granddaughter might decide shorts, a tee shirt, and flip-flops are perfectly appropriate; you may see it differently. She might think hotel room service is the height of luxury, while you’re yearning for a good pub meal. Setting expectations on both sides upfront can save friction later.

On vacation together

• Let everyone keep their own daytime schedule and meet up for cocktails and dinner. Some like to sleep late, some want to sightsee early or sunbathe. Some like bike tours, others prefer museums, gardens or stately homes. It’s not a hard rule — on a small ship like Windstar, you’ll often end up at breakfast together, or a couple gets invited to dine with new friends — but daytime freedom gives everyone flexibility while keeping evenings as family time.
• Expect dining preferences to shift across generations. We’ve noticed the younger generation tends to prefer more casual restaurants, so we adjust accordingly.
• Stay easily reachable when you’re apart. A family WhatsApp thread keeps everyone in the loop — “A great table just opened up at Star Grill, anyone interested?” or “Just caught an Uber, back on board in 15 minutes” — so plans (like dinnertime) can shift in real time.
• As host, decide how much responsibility you’re taking on for everyone’s comfort. With just the two of us, it’s easy — if something goes sideways, Brooke and I sort it out together. With six people, even agreeing on a restaurant and getting a reservation can get complicated. And where two of us would normally grab a train, taxi, or Uber from airport to hotel, with six I add van transfers to the plan.
• A good example of our different interests is a review of the hundreds of photos we as a group posted on Google Photos during our three-week trip.  Some were cathedrals and architectural while others were botanical gardens; some were landscapes while others were monuments or battlefields.  All of us posted shots taken in fresh markets and of food!  In viewing them it quickly became apparent whose interest was reflected in our growing album — and it got so we could identify the photographer by the subject.

And last, but by no means least:

• Don’t hesitate to ask a fellow passenger to take photos of you as a group … otherwise someone is always left out (unless you like selfies).

Have you traveled as a multi-generational family? Care to share any tips? And if you’re planning a trip like this and have questions, leave them in the comments below (scroll way down!) and we’ll get you answers.

The post Multi-generational Cruising: How One Family Continues a Travel Tradition appeared first on Windstar Cruises Travel Blog.

Whether you’re planning your first trip to Italy — or considering a repeat visit — here are 15 of our favorite dishes to try, ranging from north to south and in between. Did we miss your own special dishes? Drop us a note in the comments. 

At a Glance: 15 Italian Dishes by Region

How to Read an Italian Menu: Antipasto, Primo, Secondo & More

Italians eat meals differently than Americans might be used to — restaurants offer several courses with much smaller servings. You can choose something from each course or select what looks best to you. Regardless of your method, an Italian menu will likely look like this: 

• Antipasto: Antipasto or antipasti are the appetizers. Here you’ll find salads, cheese plates and many local appetizers. 
• Primo: This menu section houses the pasta dishes or first courses. If you are going to Italy for pasta, remember this word, as Italian restaurants organize their dishes by course over category. 
• Secondo: The second-course section contains meats and seafood. These selections will include all types of meat, including regional dishes you can only find there. 
• Contorni: If you want a side, look to this section. You’ll find offerings similar to those in the antipasto section, like cheese platters, salads and more. 
• Dolci: After dinner, your waiter might give you an additional, smaller menu with a list of desserts. Enjoy options like cannoli, gelato and tiramisu. 
• Digestivo: Your dessert menu might also have a digestivo section with drinks that Italians use to help them digest. Here you’ll find espresso and liquors, including limoncello, grappa, amaro, cynar, amaretto and sambuca. They’ll often come in a shot glass, and the preferred drink will vary depending on the region. 
• Vino: Did you know that Italy has 20 different wine regions? Perhaps most famous is Tuscany, which is full of outstanding regional wine and many restaurants across the country will partner with local vineyards to bring you excellent house selections. And visits to other parts of the country, such as Sicily, the Veneto, Campania, Puglia, and Friuli-Venezia Giulia (among others)!

15 Traditional Italian Dishes and Drinks to Try

With Italy’s rich food culture, Italians eat everything from pasta to seafood to rich meat dishes. Each region has unique dishes for you to try, ensuring you always have something tasty to eat. The country has many famous foods, from prosciutto di parma and olive oil to lasagna and gelato. However, knowing what to look for on the menu can help you find the best Italian cuisine, especially if you are unfamiliar with the language. 

Italian Favorites You’ll Find Nationwide

1. Homemade Regional Pasta: Tagliatelle, Tortellini, Orecchiette, Gnocchi & Pici

In Italy, Christmas meals feature rich pastas./Shutterstock

A trip to Italy wouldn’t be complete without trying some fresh, homemade pasta. Many restaurants make their pasta in-house and offer famous regional dishes that you simply have to try there. Trying regional pasta is a great way to connect with that area’s culture while having the best food there is to offer. Some regional pasta includes: 

• Tagliatelle: These long, thick pasta strips originated in the Emilia-Romagna region, host to the city of Bologna. You can find them with truffle or bolognese sauce. This dish is a must if you see it on a western Italian menu. 
• Tortellini: Also hailing from Bologna and Emilia-Romagna, tortellini is another classic you must try. You can find them stuffed with cheese or meat and in various dishes, from bolognese sauces to soups. 
• Orecchiette: Translating to “little ears,” this round pasta hails from the Puglia region in southern Italy. Puglia restaurants typically serve it with broccoli, so look for this on the menu for an authentic pasta dish. 
• Gnocchi: While you can find gnocchi all over Italy, it’s a must if you’re visiting Rome. The Romans make these heavenly soft potato dumplings fresh on Thursdays and serve them in various ways to fit your tastes. 
• Pici: A staple of the Tuscany region and Florence, pici is similar to spaghetti but thicker. You can find it served with meat sauces and dishes, where it can soak up and complement the dish’s rich flavors. 

2. Authentic Gelato 

How is gelato different from ice cream? Food and Wine tells us this: “gelato has a lower milk fat content than ice cream, usually 4 to 9 percent, yielding a softer, denser texture and smaller ice crystals. That’s a result of the base, which typically includes less cream and more milk, as well as a slower churning process that introduces less air into the final product. The base generally does not include eggs, but it can. Gelaterias also keep their cases at a warmer temperature than most ice cream shops, which contributes to gelato’s silkier texture. Although there’s no legal standard for gelato in the U.S., the Italian government requires a milk fat content of at least 3 percent.” 

Some signs of a homemade gelateria include: 

• Colors: Authentic gelato places will have natural flavor colors over bright, colorful batches. Pay attention to flavors like mint and pistachio, which are often dyed to appear more appetizing. 
• Containers: Gelaterias that ship gelato in or store it will use big open containers. The gelato will often sit up high for travelers to see through the glass. A homemade batch will sit in a closed metal container to keep it fresh and protected. 

Finding a local gelateria can help you find some of Italy’s best food. If you want to eat like the Italians, try hazelnut or pistachio. Stracciatella is another classic Italian flavor with a vanilla base and small chocolate chips spread throughout. 

3. Cappuccino and Espresso 

While many cultures celebrate their premium coffee, nothing beats Italian cappuccinos and espressos. You’ll seem more like a local in Italy by knowing when to order which.

Cappuccino is a morning drink similar to Americans’ morning coffee. Italians brew them at the perfect temperature so that you can drink them immediately. On the other hand, espressos are a digestive drink that Italians have after dinner or in the evening. You’ll find them on many menus alongside desserts or other digestive drinks. 

Favorites You’ll Find in Northern Italy:

4. Ossobuco (Milan)

For another meat option, consider ossobuco. This dish comes from Milan and the Lombardy region in the north of Italy. Ossobuco is a bone-in veal shank slow-cooked in a meat broth with vegetables and white wine, resulting in a rich, tender, juicy meal. Many restaurants serve it with polenta or risotto.

Because of how long it takes to cook ossobuco, you might only rarely find it on menus. Be sure to treat yourself to the experience if you come across it, especially in Lombardy.

5. Risotto (Northern Italy)

Traditionally thought of as a rice dish produced in northern Italy, the combination of superb recipes and top-notch crops of rice are being explored by chefs from Palermo to Turin.

6. Pesto alla Genovese (Liguria)

Pesto, best known in the region of Liguria (home to Genoa and Portofino) is a favorite pasta sauce, using crushed fresh basil, garlic, pine nuts and Parmesan cheese. If you’re a purist, you use a mortar and pestle to carefully grind the ingredients so as not to bruise them.

Beyond pasta, pesto makes a great sandwich spread and a cocktail dip.

7. Polenta

Polenta is another historical peasant dish many restaurants continue to serve in Italy. While you can find it all over the country, it originated in northern parts of the country, including Milan, Turin and Venice. Polenta is a starch dish commonly made from finely ground corn that takes many forms, from mush to fried slices.

This Italian food is exclusively a side dish. You’ll commonly see it paired with rich meats with plenty of sauces. You’ll often find it during the colder months because of its popularity alongside warmer comfort food.

Favorites You’ll Find in Central Italy

8. Florentine Steak (Bistecca alla Fiorentina)

Florence is the home of many rich dishes and drinks, and Tuscany is a popular destination for visiting vineyards and tasting traditional dishes. Florentine steak is a thick t-bone cut fresh from cows raised in Tuscany. The Florentines favor a high cut with lots of muscle, giving the steak an excellent flavor. Pair it with a house red wine for an authentic Tuscan meal.

When ordering this steak, know that it’s only available very rare. Many restaurants prepare it by cooking it for a few minutes so the outside sears, leaving a soft, rare middle that melts in the mouth. While restaurants also often charge by the steak’s weight, its thickness makes it perfect for two people to share.

9. Ragù di Cinghiale — Wild Boar Ragù (Tuscany)

If you like meat sauces and lasagna but want to try something new, ragù di cinghiale is the way to go. This traditional Tuscan dish is easy to find in Florence and features a wild boar sauce. The animal is common in the region, ensuring a rich, fresh meal you can’t find anywhere else in Italy.

Because of its thickness, many restaurants in Florence pair the cinghiale sauce with pici or thicker flat pasta like pappardelle. The pasta and sauce can be heavenly when you find a place that offers house-made pasta. Order a house red wine to complete the experience.

10. Ribollita (Tuscan Bread Soup)

While many travelers go to Italy for pasta, the country has a wide variety of foods for you to enjoy while visiting. Ribollita is a Tuscan vegetable soup. It was historically a peasant meal, rich in local, in-season vegetables that the lower class could easily access. Today you can still find it full of recent harvests, making it common in the fall when Italian farmers are picking their crops.

Instead of meat, ribollita uses bread to thicken and flavor the soup. It’s savory and hearty, and many Italians choose it on chillier days to help them warm up.

When traveling in Tuscany and Florence, it’s common for restaurants to list ribollita as a first-course dish along with pasta courses.

11. Spaghetti alla Carbonara (Rome)

When in Rome, eat as the Romans do. The capital city is home to many famous Italian dishes, including carbonara. Typically served with spaghetti, carbonara is a sauce made from eggs, pecorino cheese, cured ham and black pepper. Many Roman restaurants serve it with fresh pasta as their house special.

If you want to find the best carbonara in Rome, ask the locals or go off the beaten path. Trastevere is a neighborhood in Rome famous for its restaurants and Italian cuisine, making it a great place to start if looking for a good carbonara. The brightly colored buildings and draping vines add ambiance to your meal when eating outside.

12. Truffles (Tartufi)

Truffles, a type of mushroom that grows in Tuscany, Umbria and Piedmont, are some of the best foods to eat in Italy. These regions often train dogs and pigs to sniff out truffles to use in traditional dishes.

Truffles have a unique smell that gives dishes a distinctive taste and draws avid food-lovers to them. You will often find them over pasta or in sauces, especially in the fall, when they are more common.

Favorites You’ll Find in Southern Italy & Sicily

13. Margherita Pizza (Naples)

If you find yourself in Naples, you must try traditional Margherita pizza. This Campania city considers itself the birthplace of the classic dish that became popular when Queen Margherita visited in 1889. This pizza has a simple tomato sauce topped with fresh mozzarella and basil leaves. Now Naples is famous for its various pizzas, including the Margherita.

When ordering pizza in Italy, be sure to translate any Italian ingredients beforehand. Pepperoni translates to peppers in Italian — expect to receive a pizza topped with green or red vegetables when ordering a pepperoni pizza.

14. Bottarga (Sicily)

Bottarga is a traditional Sicilian dish made from the roe of gray mullets, which Sicilians will salt, press and air dry for months to create a savory, smokey flavor.

Restaurants buy and serve their fish fresh for the best tastes you can find. You will often see bottarga shredded or sliced over pasta. Restaurants will often pair it with lemon juice or olive oil because of how the flavors mix.

15. Arancini and Supplì

While the thought of Italian food might conjure images of sipping wine at elegant outdoor restaurants each night, street food is popular and tasty in Italy. Arancini and supplì are two types of fried rice balls from different Italian regions. You can find these great to-go appetizers at market stalls, restaurants and bars.

Sicilian arancini have a distinct triangular shape, making them easy to hold and carry around. Most places will fill them with ragù sauce and cheese, though you might have the option to add vegetables like peas, mushrooms or eggplant.

Supplì are from Rome. They have an oblong pill shape and contain tomato sauce and mozzarella instead of ragù. The cheese usually melts, pulling apart when you split the supplì in the middle. Supplì are standard antipasto options in Roman pizzerias.

Frequently Asked Questions

What’s the difference between gelato and ice cream?

Gelato has less milk fat, less air churned in, and is served slightly warmer, giving it a denser, silkier texture than American ice cream.

Should I order a cappuccino or an espresso in Italy?

Cappuccino is a morning drink; espresso is what Italians order after a meal, in the evening, as a digestivo.

How is an Italian menu structured?

By course, not category — antipasto, primo, secondo, contorni, dolci, and digestivo, rather than starters/mains/dessert.

Read more about Italy

Whether it’s your first visit or you’re an expert, check out our recent blogs on crafting a magical Italian experience in the Mediterranean: 

• One traveler discovers why winter in Venice offers surprising perks. 
• In the village of Portofino, on the Italian Riviera, we share our favorite food and drink. 
• Emiko Davies is one of our favorite Italian culinary experts (she’s also considered top notch when it comes to Japanese cuisine); we love her blog on all things cuisine-related.
• What is it like to cruise a classic Mediterranean voyage in winter? We loved it. Here’s our story. 
• Curious how small ships get you into ports the big lines can’t? Here’s our guide.

The post 15 Must-Try Regional Food and Drink Specialties in Italy appeared first on Windstar Cruises Travel Blog.

The hardest part is usually agreeing on where to go. What if one friend wants beaches, another wants a city, and a third wants culture and cuisine? A cruise solves that problem before it starts. With multiple destinations built into a single itinerary, everyone in the group gets their version of the perfect trip, without the group chat debate over which single place makes the cut.

“At the end of the day you’re traveling to experience a new culture, a new country, and getting out of your comfort zone,” says Zulay Labra, who’s currently planning a Tahitian cruise on Star Breeze with friends she met on another Windstar voyage. “With friends, though, you’re traveling in a comfortable way. And taking a cruise comes without the anxiety of planning everything independently.”

We’ve picked a selection of cruise regions that really do offer something for everyone to enjoy, whether it’s culinary, active exploration, big city museums or local culture. Or all of them! And at the end of the day, remember this: It’s perfectly okay to go in different directions during the day, and then reconnect for cocktails and dinner to share experiences. 

Alaska and British Columbia

Alaska is an unforgettable destination for your friends with diverse . The state contains a wide range of natural landmarks, from glaciers and shorelines to breathtaking mountains and crowded cities. Alaska is famous for its natural beauty and wildlife, making it an excellent option for friends who love the outdoors. Possibilities include bear trekking, kayaking, hiking, and flightseeing. This region is also well known for its fantastic microbrews; in Ketchikan, in particular, both Baleen Brewing Co. and Bawden Street are worth visiting. 

Tokyo on a mostly around-Japan voyage

Another example of the best places to go on a trip with friends is Tokyo, Japan. Asia can be a multi-faceted trip for adventurers and it’s nice to have pals along to share discoveries. Tokyo is a fast-paced and beautiful city, known for its technology, historical sites and delicious food. It has a unique blend of modernity and tradition, with new skyscrapers resting next to ancient temples.

The busy streets of Tokyo have much to offer for travelers. From endless shopping opportunities to interactive museums, you and your friends can find activities that match your interests. You could visit the Sensoji Temple, the oldest religious site in Tokyo, or explore the Tokyo Skytree. Or, you could explore Akihabara, a neighborhood dedicated to manga and electronics. No matter how you spend your time, be sure to taste Tokyo’s extraordinary food, from sushi to tempura.

Because of Japanese cabotage restrictions that require around-Japan itineraries to call in at least one foreign port, most Windstar cruises visit the fantastic “Los Angeles of Korea” city of Busan. 

Circumnavigating Iceland

Iceland is a one-of-a-kind travel experience in which craggy natural scenery and cosmopolitan towns and cities. The country’s dramatic landscape features volcanoes, mountains, glaciers, hot springs and more. Its capital city, Reykjavik offers art and cultural experiences like the National Museum of Iceland and the National Gallery of Iceland. Akureyri, its second largest city, is home to the North Iceland Symphony Orchestra.

And yet, what both also offer to diverse groups of travelers is plenty of expedition-type exploring. 

What may surprise you about Iceland is how delightful are the ports that you may never have heard of. In Grundarfjordur  Snæfellsjokull National Park is magically full of regal glaciers, lava fields, waterfalls, caves, calderas, and basalt cliffs. In Seydisfjordur, spend a few hours chasing waterfalls and then attend Windstar’s exclusive Destination Discovery Event, Sagas & Songs at the Blue Church. Nested between mountains that are snowcapped even in summer and the sea, Isafjordur is a charming small town, perfect for just strolling and it’s also home to Dokkan brugghús, one of Iceland’s best breweries. 

St. Maarten/St. Martin and the Eastern Caribbean

Hankering for the Caribbean? St. Maarten, a departure port for many Windstar cruises, is part of a two-nation island. The Dutch St. Maarten is the spot for nightlife, casinos and an awesome zipline experience. The French St. Martin is better known for its culinary fusion that blends Creole and French techniques, its duty free shopping, and the lively bustle of Marigot, a market town. Both have plenty of beaches, all with different personalities and in both cases water-based sports, from kayaking to parasailing, are plentiful. And you can easily travel between the two as there’s no border control. 

Choose an itinerary that spends time in the British Virgin Islands and St. Barts for the perfect balance of sophisticated shopping and dining and just-chillin’-out. 

Costa Rica and the Panama Canal

Another tropical destination for your group of friends is Costa Rica. This gorgeous location has a diverse range of nature, from rainforests to volcanoes. If you have any animal lovers in your group, Costa Rica is full of exotic wildlife you can view up close. Watch a rare bird soar through the sky or spot a shark in the blue water.

You can rest on the beautiful beaches or sample the tasty local food offerings. Costa Rica also offers various wellness activities, like immersive body wraps or hydrotherapy. It’s an ideal place for refreshing and relaxing from work or other life stressors. And once you learn new relaxation techniques, you can integrate them into your lifestyle at home. 

Athens and the Greek Isles

Athens is a popular home port for around Greece voyages. Itineraries typically depart from Athens, so plan a pre- or post-cruise stay there before heading out to remote islands, picturesque villages and fabulous beaches. In Athens, you can immerse yourself in Greek culture and the elegant landscapes. Athens is one of the world’s oldest cities, displaying centuries of history and culture. Greece is an unforgettable vacation spot, with breathtaking landscapes and historical monuments. You and your companions can visit everything from historical temples to theatres, either on foot or on a bike. Athens has endless opportunities for dining, exploration and leisure, allowing your travel group to create an itinerary that matches your needs.

Italy’s Venice and the Adriatic Sea — in winter!

There’s a lot to love about an off-season (winter) Mediterranean voyage that travels between Venice and Rome by way of the Adriatic Sea. An Adriatic cruise that departs from (or arrives at) Venice is a classic destination for world travelers.  Plan to arrange for a few days in La Serenissima before heading out to Croatia, Kotor, and Italy’s Sicily and Sorrento. Advantages to an off-season voyage? Attractions and museums are open — and uncrowded. Dining reservations are easier to secure. And discounts abound from pre- or post-cruise hotels to the voyages themselves.

In Europe, visit London, Amsterdam and Bruges on Quick Getaways 

New for Windstar is a series of short European sailings that are a perfect way for busy pals to commit to a trip together. Quick Getaways: Belgium: A Sweet Getaway is a four night sailing that sails down London’s Thames and visits the Belgian cities of Bruges and Antwerp before returning to London.

Other options include the four night London-based St. Malo getaway to visit Mont St. Michel, truly a bucket list destination, and Seaside Charms and Dutch Waterways, a three night trip from London to Amsterdam by way of Bruges and Harlingen. Want an onboard overnight on the Thames? The five night Timeless Maritime Powerhouses sails from Amsterdam via Antwerp and Normandy’s Honfleur, before docking in central London. 

French Polynesia’s Tahiti, Bora Bora and Huahine

Tahiti is another one of the best places for travel, characterized by clear waters, thick forests, luxurious resorts and French cuisine. This remarkable island provides the ultimate relaxation experience, surrounded by warm sunshine and fresh fruit. It’s one of the best beach vacations for large groups.

One of the top ways to experience Tahiti is by cruise. You and your friends can ride through crystal-clear water to reach this paradise-like island. Once you’re there, explore the nearby waterfalls and gardens. Or, spend all day on the beach, with its pure white sands and clear blue waters.

The post Friends Who Travel Together, Stay Together: Where to Go Next appeared first on Windstar Cruises Travel Blog.