Guide to Old San Juan and Culebra – Puerto Rico

Traveling to Puerto Rico for the first time was such a special experience! My mom is Dominican/Puerto Rican, and was born in Arecibo before coming to the United States as a baby. Growing up, I always felt a disconnect with being Puerto Rican, being that I had never visited or met any family from the island. However, it has always been important for me to travel to all the countries where my family is from… and it’s safe to say that I fell in love with Puerto Rico.

Where to Stay

Casa Moderna in Old San Juan was a dream! The location was everything you could ask for – steps away from a CVS, amazing restaurants, close to the water, and easy for Uber to locate. The AirBnb itself has 2 bedrooms, 2 baths (both standing showers), a BEAUTIFUL balcony with partial water view (pictured above), A/C, WiFi, washer/dryer: the works. Get $30 off your booking by clicking here. A few tips:

  • Upon landing at San Juan Airport, take a taxi to the AirBnb (about 20 mins) – Uber cannot pick you up from the airport, but they can drop you off.
  • If you want to rent a car, there is a parking garage nearby. We rented a car for one day, but dropped it off the same day to avoid dealing with parking.
  • The owner Karl is a friend of mine, so be sure to mention me when booking! He also has other properties in Puerto Rico and is a super host.

Where to Eat

To make things easy, I created a Yelp bookmark with all the recommendations I was given, as well as the places where I actually ate here! Please note: many places need either a reservation, or you need to put your name on a waiting list early! The earlier you can knock out your day activities to get to a nice dinner, the better. So if you’re a go with the flow, wing it person but you want to experience the best places to eat, take some time to plan this piece out. Honorable mentions:

  • Breakfast – Mallorca: A crispy, buttered, Puerto Rican bread sprinkled with powdered sugar *drools*. Tons of locals and tourists alike come here to start their day with a mallorca (I did mine with ham and cheese) and a cafe con leche. It sounds like a lot especially if you’re not crazy about sweets but just trust me on this.
  • Tacos – Kabanas: A 10 min Uber drive (close to all of the resorts), there is nothing ordinary about their tacos. They come loaded, with so much flavor and a unique shell that has melted cheese on it…Their house sauce called Pique PaTi needs to go on all of your tacos.
  • Best Mofongo – Punto de Vista: I will dream about this garlic sauce for the rest of my life. They don’t take reservations, however if you get there around 6p.m. you can put your name on the waitlist for dinner. You can also go for lunch, however dinner is where it’s at since it’s on a rooftop. You don’t need an appetizer since the mofongo is super filling, but the mahi bites were delicious! I personally went with the chicken and shrimp mofongo and it did NOT disappoint. Paired with one of their mojito’s and you have a classic Puerto Rican dinner.
  • Dessert – Senor Paleta: Don’t get scared away by the line outside of the door, it’s there for a reason! While I only had the strawberry cheesecake Popsicle, it was delicious! You could tell a lot of locals go there, and they have a wide variety of options from passion fruit to nutella.
  • Coffee – Don Ruiz: With all the eating that I was doing,  I needed a nice balance of caffeine to keep me awake. Located near Castillo del Morro and “that door with the Puerto Rican flag on it” – take a break and enjoy some delicious coffee by the water. It’s inside Ballaja, a building with a huge beautiful courtyard (also perfect for pictures.) If you want to bring back some coffee beans as a gift, this is the place to go.

What to Do

I spent 4 days and 3 nights in Puerto Rico, and my trip went a little like this:

  1. Day: Act like you’re staying at La Concha resort and lay by the pool. While I loved my AirBnb, I wanted a place to lay by the pool/beach and relax a bit since I had an early flight landing at 8am. La Concha is a beautiful resort (close to Kabanas tacos, so don’t eat at the hotel), and I tipped the towel man so I could lay by the pool. Night: Bar hopping at La Placita de Santurce. My nap lasted a little later than expected, and since we didn’t have dinner reservations we headed to La Placita to grab a quick bite before bar hopping. Ask any local where to go for nightlife, and they will say La Placita. It’s basically one huge block party with bars that play all types of music. We went on a Friday night, although a few people suggested we try Saturday.
  2. Day: Rent a car to El Yunque National Forest. There’s an Enterprise right by La Concha, where we rented a Jeep to head to El Yunque (which was about a 45 minute drive). You don’t need a tour guide, just follow the signs to the visitor center and you’ll be directed on where to go. Wear waterproof shoes, and bring a sweater/rain jacket just in case it starts to rain. Before heading back, grab a bite to eat at Degree 18 Juice Bar, the cutest and freshest juice bar ever. Night: Dinner at Verde Mesa, an upscale eatery where 2 drinks, an appetizer, 3 entrees and dessert was around $130 (something that would’ve cost way more in Miami). After, we wandered to San Sebastian and went bar hopping there.
  3. Day: The highlight of my trip – taking a small plane to Culebra for the day! My honey planned this and it was such a beautiful experience. We used Air Flamenco to fly from San Juan to Culebra (you can only get there by ferry or plane), and the ride was about 30 minutes. This flight gives you the most amazing view, but it can definitely be a little scary. Once we got to the island, we rented a Jeep (again) from Carlos Jeep Rental which is across from the airport. The island is very small, so the car allowed for us to drive around and head to the beautiful Flamenco beach. My only regret is that we didn’t stay overnight in Culebra, which is what everyone around us recommended. It was hard to find food places that were open, so we grabbed lunch by the beach and enjoyed the view.
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Culebra is a small, sparsely populated island and surrounding group of cays off the east coast of Puerto Rico. In the northwest, Flamenco Beach is a long crescent of white sand and turquoise water backed by tree-covered hills.

3. Night: Dinner at El Punto de Vista and salsa dancing at La Factoria – recently named one of the top 50 bars in the WORLD. Everyone will tell you this is the place to go for Salsa music, but they forget to mention that Sundays are for the real salseros. I danced more Salsa this night than I have in a really long time (to burn off all the mofongo I ate). They also have a wide variety of craft cocktails and a live salsa band.

When your flight is in a few hours and you’re two mojitos in 🙂

On my last day, I had a 6p.m. flight so I decided to roam around Old San Juan. I went back to Punto de Vista since they had buy one get one mojitos, and took some pictures around the beautiful city before heading to the airport.

If there was one thing I could change about the trip, it would be to stay an extra day so I could do an overnight in Culebra! I had a truly unforgettable experience, and I can’t wait to go back.



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