Day 1: New York to St. Louis

We embarked early and headed to St. Louis. This was a straight forward drive with the only thing to note is that when we showed up in St. Louis all the good looking BBQ places were CLOSED. I think we finally showed up between 8-9 pm, and ultimately ended up getting food from the Burger King next to the parking lot of our hotel. So be warned, show up early to St. Louis, or eat Burger King.

Day 2: St. Louis to Denver (New Year’s Eve)

The weather was cold but clear and we were making good time. We hit Denver early enough that we could celebrate New Year’s Eve on the town. Even though we had an event picked out and everything, we ended up being super lazy and stayed in. We hit the liquor store across the parking lot of our hotel, got crappy champagne, good beer, and then ordered Dominos. Burger King, Dominos and booze, we are committed to a healthy lifestyle.

Day 3: Denver to Las Vegas

The next morning, we moved a little slower because we wanted to hit a restaurant we love in Denver called Snooze. They are a Denver staple, but also have a location in San Diego, which is where we first discovered them. We crushed a lavender pancake and a benedict, and then headed to Vegas.

Day 4 – 8: Las Vegas

Jill and I had very different experiences in Las Vegas. She basically had to work from morning to night the whole week at CES, while I worked remotely, and got a lot of climbing and video games in. The highlight was definitely climbing at Red Rocks and warranted a separate post, read my Red Rocks Climbing Trip Guide here.

I was pretty sad to leave Las Vegas. Red Rocks completely changed my perception on the city. The strip is often what gets talked about, but the amazing mountains surrounding it are the real feature. It’s desert nature at its best.

Day 9: Las Vegas to Reno

Vegas to Reno is a quick seven hours and the drive is pretty beautiful. This time we made plans and semi-stuck to them. We had dinner at this great French restaurant named Beaujolais Bistro. We planned on heading in and seeing a little bit of Reno’s version of the strip, but again wimped out and went to bed instead.

On the way to Reno is when the weather started to get whacky. There was a huge storm blowing across northern California coming from the coast, and Reno was slated to get some serious flooding from the Truckee river. Luckily for us, the Sierra Nevada mountain range was going to hold the storm off long enough for us to bail to Eugene.

Day 10: Reno to Eugene

This is also supposed to be an easy seven hour drive, but we got hammered with rain, and the Cascades were icey. In addition, while we were headed across the country, the forecast in the Willamette Valley, where Eugene is, turned bad. Eugene and the surrounding areas essentially froze. This slowed us down to a crawl during the approach to Eugene, but we made it safely.

Day 11 – 15: Eugene

Eugene is home. I grew up here and whenever I go back I try and chill as much as possible in my parent’s backyard and make sure to do a tour of the restaurant hits. A few of the Eugene classics I try to fit in are:

• Track Town Pizza
• Beerstein
• Cornucopia
• The beer holy trinity in the Whiteaker area
  • Ninkasi
  • Oakshire
  • Hop Valley
• Off The Waffle
• The David Minor Theatre
• Belly Taqueria
• Pizza Research Institute

And some of the new places (or Portland imports) that have popped up since I moved

• Izakaya
• The Barn Light Cafe and Bar
• Tailored Coffee Roasters
• Sizzle Pie
• Voodoo Doughnut

After some quality family time (and local food, beer, and wine, duh) it was time to make the trek back to New York. The roads were not looking good, and eastern Oregon was a frozen tundra with temps reaching as low as -4.

Day 16-19: Eugene to Boise to North Platte to Toledo to New York

The rest of the trip was a grind and was pretty high stress. I white knuckled the steering wheel across the country as we avoided ice, and the drive took much longer on the way back because of it, but we ultimately made it back home without issue.

I fully believe that every person that can, especially people living in the US, should do a cross-country drive at least once, but would recommend doing it in late spring / early summer or late summer / early fall. While it was amazing to see some incredible landscapes in snow, the driving was pretty awful and overshadowed the views.

For my trip, surfing was an active rest day activity between climbing days (read my climbing trip guide here), which meant I was looking for moderate size waves, and I rented boards as opposed to bringing mine. I scoped two locations, the first was Surfer’s Beach because I heard it was a solid break and had some boulders on the beach that could be climbed, and Sandy Beach because it was also a great spot to lounge after a session.

If you want to read more about what I did for lodging and food you can read my Puerto Rico trip travel guide.

The Breaks

Surfer’s Beach | Map Link

Break Type: Reef, rock bottom

Skill Level: Intermediate and up

Where to rent a board: Surf Zone | Map Link

This shop is your classic surf shop. The board rentals are in the back. They have a solid selection and the boards are nice. The waves were overhead the day I went so they wouldn’t provide me a leash because of the risk of breaking it, so I had to buy my own.

I am not sure they do this every time you rent, but the guy that was working at the time took me to the Officer’s club’s balcony next door and showed me the break. He gave me a run down on the water, current, and what to watch out for. It was really cool of him to do that. Also, this is the closest shop to the break, so convenience is very high.

Parking and Amenities:

There is a free and pretty large parking lot right at the beach. There are no other amenities.

The Waves:

It was big the day I went out. The waves were consistently overhead. There wasn’t really a trick to paddling out, you just had to take it on the chin. I was pretty exhausted after I got passed the breakers and into the lineup.

I was on a shoulder mainly picking up rights, but the main break a-framed. It’s also important to note that this break can be tricky because there is a longshore current that takes you southwest towards a big grouping of rocks that are loaded with urchins. I was warned about this, and even then I still got pushed into the beginning part of the rock formation when I paddled in. I luckily didn’t get an urchin in the foot, but it was definitely sketchy.

Sandy Beach | Map Link

Break Type: Reef, rock bottom

Skill Level: Beginner and up (wave size permitting)

Where to rent a board: Mar Azul | Map Link

Mar Azul is small but they have a good board selection, all of which are nicely maintained. They will do a thorough ding check so be vigilant when transporting your rental. They’ll provide roof racks if you need them.

Parking and Amenities:

There is a very small amount of parking right at the beach, otherwise you need to find parking on the street. There is a little snack shack that has non-alcoholic cold drinks and chips and stuff. As we were leaving, we did notice that we had overlooked a bar at hotel nearby, huge miss.

The Waves:

The size was much more manageable this day. There is no secret to paddling out, just time it right between sets and push through. It’s a very straight forward break with no major dangers. The size was probably 3-5 feet, and it held it’s shape nicely. There was a longshore current this day too that took me west.

What piqued my interest most was the access to nearly all climbing styles. There is single and multi pitch sport, trad, bouldering, and deep water soloing, all on an island you can drive around in a day. While weather, energy, and time prevented me from bouldering and deep water soloing as planned, I was able to sport climb at three different crags and had an awesome time.

If you want to read more about what I did for lodging and food you can read my Puerto Rico trip travel guide.

The Plan

Originally, the idea was to sport climb at three separate crags across the island, do some fun bouldering during one of our surf days, and do some deep water soloing as well. Ultimately, the trip was simplified to just sport climbing.

What I climbed

I picked three crags spread out across the island. Each of which have digital mini-guides that you can buy online, I’ll link to each below. The guides were put together by a local company that has a physical climbing/outdoors store located in San Juan, and also offers guiding services.

https://www.aventurastierraadentro.net/

Area: Rosario / San Germán

Guide book

Parking: Free | Map Pin

This crag was challenging. It featured powerful climbs and stiff ratings, and not a lot of great warm-up options. It was also a little weird because it’s located on private land.

The mini-guide notes that it’s on private land and said they haven’t had any issues as of writing the guide, but I did get approached by a guy driving past where I was parked. He asked if he could “help me”, but he was really trying to probe what I was doing. I think it was obvious to him I had been climbing and he asked if anyone else was back there (there wasn’t). He did not seem stoked. With that said, I might check in with the mini-guide authors and get the landowner’s current vibe before making the trek.

This area’s grading starts pretty tough. The lowest grade climb that isn’t a 2nd pitch climb or above is a short, but stiff, 5.9 on 45 degree wall.

Wall: Vertical Jamming

I went up a two pitch route named Los Balcones de Miyagui (Pitch 1: 5.10a, Pitch 2: 5.9). I had trouble with this route at the start, pretty sure I flash pumped, or adrenaline dumped.

The beginning wasn’t easy and the gear felt sketchy to start (three pitons and a fixed nut), then it was bolts the rest of the way up. I felt confident I could climb the route, and the gear held when I tested it, but being the first climb of the trip in an unfamiliar area I think I psyched myself out and made it harder on myself then it actually was.

I ultimately had a great time, and finished the first pitch, but was too pumped part way into the second pitch and didn’t finish it.

Wall: The Gym

All the routes are pretty short here but very muscley and on a 45 degree wall. I tried the easiest route on this wall and got worked. It’s called Piel de Serpiente (5.9). I know I could do this on a fresh attempt, pretty sure I didn’t let myself recover enough from the previous climb, and also managed to z-clip twice which never helps get you to the top.

I would definitely like to come back to this crag now that I know what I am up against. I noticed a bunch of boulders around the area and will probably spend more time warming up on those, or figure out some sort of traverse on The Gym.

Area: Las Tetas

Guide Book

Parking: Free (need a padlock code listed in the guide book) | Map Pin

I hit Las Tetas after climbing at Rosario/San Germán. I really liked this crag and wished I could have climbed much more here. The climbing session was limited to one 80 foot route that paid off with a stunner of a view.

The route was called Flake City (5.9). It’s a long climb with more or less obvious holds, and fun movement. It was a bit windy that day which made it a bit of an ass-clencher higher up, but overall was a great climb. It is a perfect warm-up route.

I would probably spend a full day here. There is a decent volume of climbs that seem more fairly graded than Rosario, and some awesome looking multi-pitch potential.

Area: Nuevo Bayamón

Guide Book

Parking: $3 | Map Pin

Nuevo Bayamón is the most easily accessible and has the greatest volumes of climbs. It is also located closest to San Juan (~25 minutes from Old San Juan) in the Julio Enrique Monagas National Park.

Wall: Sector 2: La Escalera

This was the last day of climbing so I went for volume of climbs. The grades felt accurate here. This area was nice and shady, but it was also probably the most humid of all the areas. I onsighted four routes:

• Paz 5.8
• Amor 5.9
• La Cueva del Alacrán 5.8
• Yan Gabriel 5.9

I only got a half-day in here and really wanted to try a route called The Shark Attack (5.10d), but ran out of time. It has a strong overhang finish and is known to have sharp holds like shark teeth hence the name.

Overall the stoke stayed at 100 the whole trip. I would go back in an instant, and highly recommend you do as well.

What I missed

Bouldering didn’t happen because I was dead-ass tired from climbing the day before, and then surfing the day of. I read about some fun rock formations at Surfer’s Beach, which also has a great surf break and is aptly named. I didn’t find any grading or guides for these boulders.

Surfer’s Beach map pin.

I really wanted to try to deep water solo the arch near Cuevo Del Indio. The route is known as Marejada Feliz (Happy Surge). Since I was there in February it was still stormy and the waters were rough, which meant not great for taking a fall so I passed on it.

Cuevo Del Indio map pin.

My wife and I chose to stay for the majority of our time near Rincón on the west side of the island. This choice was mainly for access to surf breaks, but we were pleasantly surprised with the chiller vibe away from San Juan. And as an added bonus, the driving we had to do allowed us to see much more of the island than we probably would have had we stayed in San Juan the whole trip.

Getting Around

As I just mentioned, we drove, a lot. Renting a car was super easy and we did so at the airport. Taxis are an option in San Juan, and Uber is there now. I also read about riding the bus, but for our needs we either walked or drove.

Parking

Parking was a bit tricky sometimes, especially in Old San Juan. If you are driving into Old San Juan try and hit the Doña Fela parking garage:

Map Link

If that one is full or closed, there is another garage, Estacionamiento Covadonga, close by:

Map Link

Stay

For this trip, we chose an Airbnb in a small town just south of Rincón called Añasco. We like self-catering places better when traveling, and since we weren’t staying in an area loaded with close-by restaurants it was extra important to be able to cook our own food.

The place we stayed in was very cool. It was called a penthouse, but that was only because it was on the top story of the two unit building. The building itself was literally butting up against the water in the Bay of Añasco, and you could basically launch sea kayaks from the door of the basement.

The only negative was the series of restaurants that lined the cliff above us. They played very loud music late into the night, which killed the relaxing vibe and made it hard to sleep.

We stayed in San Juan for our last night in a Hampton Inn and Suites. It was a basic hotel that had some resort amenities like a pool and a cabana bar. We only stayed here because it was close to the airport, and it was perfectly adequate for that.

Food

We essentially had an even split between eating at restaurants and eating food we bought at the grocery store.

Buying Groceries

The first thing we did after getting our car was immediately drive to the huge Walmart closest to the airport. Not necessarily a local spot, but it was easy and nearby.

Map Link

Later in the trip we bought groceries at the Econo grocery store close to Rincón. Be sure to bring your own bags if you shop at this location, or else you are relegated to using whatever leftover cardboard box is available.

Map Link

Restaurants

Picoteo

Location: Añasco

This is one of the restaurants on the cliff above our Airbnb, and we ate here the first night. The best part about this place was that it is all open air and has an incredible view of the water. The food was fine and hit the spot after traveling, but it was an intense amount of fried food. I wouldn’t go out of the way to eat here, but if you are nearby, I would get a beer and take in the incredible sunset views.

Map Link

Estela

Location: Rincón

We had a very fun time here. The restaurant is pretty tiny but can sit a lot of people because they also have patio seating. I would recommend getting a reservation so you can sit outside where the ambiance is the best. We didn’t have a reservation and were still able to get a table for two inside. The dishes themselves are what you would find in most restaurants, but the ingredients were locally sourced and the food was delicious.

Map Link

Lupito’s

Location: San Germán

A huge ass burrito and a couple beers after a hike and rock climbing session really hit the spot. We were climbing nearby and went into town for food and randomly found Lupito’s. The food and service was great, and they have a roof patio that overlooks a historic church. I would highly recommend this place if you are on the southwest end of the island.

Map Link

Tostado

Location: San Juan

Brunch here was legit. It’s definitely a popular spot so you may have to wait a bit, and we were happy to. They have a waiting area outside of the dining room that serves as a bakery/cafe type thing. We got coffees and hung out until our table was ready. The service was very friendly and the food was delicious.

Map Link

Vino Factoria

Location: San Juan

Figuring out how to get into this restaurant is not necessarily obvious, but cool none the less. To get in, you have to enter through the bar La Factoría. There is an inconspicuous door behind and to the right of the bar counter. You can just open that door and walk through. You’ll then find yourself in the wine bar, the next room after that is the restaurant. We had great cocktails, the food was delicious, and the ambience can’t be beat.

Map Link

Señor Paleta

Location: San Juan

This place cannot be missed. For those that don’t know, paletas are sort of like popsicles, but are usually way better because they are made with fresh fruit or real ingredients. For example, my wife got a strawberry paleta that had whole strawberries in it, while I got a chocolate brownie paleta that had a brownie at the core. I almost died it was so good. There was a significant line, but it moved quick enough and was absolutely worth it in the end.

Map Link

Drinking

Rincón Beer Company

Location: Rincón

Sitting in the plaza at the heart of Rincón and drinking beers was awesome. They had Puerto Rican beers on tap as well as offerings from other well known breweries from the mainland. I got the Porter Rican, which was a solid Porter, but maybe too big of a beer for how warm it was. I would highly recommend an evening here, there’s also a good amount of food options around the plaza as well.

Map Link

What We Missed

El Yunque National Forest

Missing the rain forest was a huge bummer. This would be a whole day excursion for us and we just didn’t have enough days. We will probably come back just to make sure we get to experience hiking through the forest.

Vieques

Both of us really wanted to go this island, but we just couldn’t fit it in. Like El Yunque, traveling to this island is worth coming back for. It is widely known for snorkeling, secluded beaches, and is home to one of the bioluminescent bays.

San Juan / Old San Juan

We had a mission of surfing and rock climbing so we really only spent about 18hrs in San Juan. In that time we managed to hit three restaurants, a beach, and did a stroll through parts of Old San Juan, but we missed big things like the San Felipe del Morro Fortress.

Cuevo del Indio (Near Arecibo)

I personally really wanted to see this natural arch feature. It’s a very cool deep water solo climbing spot, and I also read that there is a cool trail that takes you a long the cliffs.

Random Stuff

Bugs: We went in February and there virtually no mosquitos, which is an obvious huge win.

Weather: It was warm to hot the whole trip, but never so hot that it was unbearable. I think it only rained on us briefly one day as well. February can be a stormier season, but that just means better waves for surfing.