San Juan, PUERTO RICO – How am I just now sharing my love for the Island of Enchantment? I’m a huge “reggaetonera” and have been listening to music out of this small island for over 15 years now, before it hit mainstream. As a US territory, American tourists don’t need passports to travel here, but once you land you’ll definitely feel like you left the country.
Our Most Recent Stay
5 days / 4 nights
If it’s your first time visiting the island, Condado is a great area to stay. Here you’ll be close to restaurants, beach front, and just a short 5-7 minute drive to Old San Juan. Our favorite neighborhood to stay is Ocean Park because it’s more of a local vibe with less crowded beaches. We pick Airbnbs that provide beach towels, chairs, umbrellas, and a cooler so we can bring our drinks and snacks to stay a full day on the beach. If you’re looking for a hotel experience, I recommend La Concha in Condado.
Punto de Vista – located at the top of Hotel Milano, this terrace restaurant is known for serving some of the best mofongo! We like to go for lunch because they have 2 for 1 mojito specials before 5pm. If you want to take advantage of the view at night, stop by to put your name of the list (they don’t take reservations) and they will call your cell when your table is ready. You can’t go wrong with any of the mofongos, but the pork or shrimp are great selections.
Cocina Abierta – tapas!! The best restaurant in San Juan in my opinion! Croquetas and the tuna tataki were some house favorites. Great for date night as it is a bit nicer, but it’s 100% worth the price.
Raices – Puerto Rican cuisine with lots of choices for mofongo, traditional plates, and fried foods.
Princesa Gastropub – trust me, you’ll want to put this one on your dinner list for sure when in OSJ.
Sabrina– trendy restaurant near Ocean Park off Calle Loiza. Great cocktails!
Bebos – local Puerto Rican food!
Senor Paleta – Cool down with a popsicle or ice cream in OSJ. Order the maracuya (passion fruit) or “parcha” as they say in Puerto Rican Spanish.
Cuatro Sombras – central stop for coffee in OSJ
La Factoria – Named number 32 of World’s Best Bars and filming location for Despacito. There are multiple rooms, each with it’s own music..my favorite is all the way in the back for salsa dancing.
La Verguenza – located in La Perla. Great for people watching, dancing, live music, and energy. Look for a man selling hand rolled cigars just outside!
La Casita – cocktail bar close to the water in OSJ specializing in rum or “ron”.
La Placita – a bailar! You can find all types of music here – reggaeton, salsa, bachata, merengue – de todo! The drinks are quite strong, super cheap, and you can drink in the streets of this small plaza (think New Orleans). I recommend ordering a vodka con parcha (vodka with passion fruit), but careful…you’ll only get a splash of juice.
Old San Juan – As the oldest city in the US, there are many national historical landmarks to visit like El Morro and Castillo de San Cristobal. Wander through the blue cobblestones streets and admire the colorful Spanish architecture. Calle Fortaleza often has umbrellas covering the street which makes for great colorful photos.
Paddle Board in Condado’s Lagoon – morning activity on the water for $20/hour walking distance from the hotels.
El Yunque National Forest – a must for your first visit to PR and about 40 minutes from San Juan. Hike, bathe in the waterfalls, and learn about the diverse ecosystem including the coquí frogs.
Culebra/Vieques Trip – if you are staying in PR for a week, I highly recommend a trip to the east islands! A full day private trip to Culebra with Culebra VIP & East will run you $600-$800, so it’s perfect if you are traveling with a few friends. We had a booking for August but COVID happened, so unfortunately we weren’t able to travel. Great thing is that their cancellation policy is a full refund 48 hours in advance if your travel plans or the weather changes!
We’ve rebooked our next visit for April 2021, can’t wait to go back!