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Traveling with Anthony: 48 Hours in San Juan, Puerto Rico

Looking for a weekend getaway that doesn’t require a passport? Look no further than San Juan, Puerto Rico! With old-world Spanish charm, amazing food, beautiful beaches and the loveliest people, San Juan offers the perfect Caribbean escape.

Packing List

Booking the Trip

Take the time and do a little research. Look at travel blogs and influencer accounts to see what piques your interest. We like @discoverpuertorico, @puertoricoeats, and @placespuertorico to name a few. There are lots of affordable Airbnbs in Old San Juan and Condado, amazing full-service hotels like La Concha and dreamy guest houses like The Dreamcatcher.

Getting Around

Book your flight to San Juan Luis Muñoz Marín Airport . Take a taxi to your destination and be sure to bring cash. Most trips in the area will be around $20-25 from the airport. Uber also operates around San Juan so it’s great for getting around. You can also rent a bike at Bike Rent Puerto Rico and The Dreamcatcher, and if you stay at La Concha they offer complimentary beach cruisers to ride around Condado.

San Juan Eats

Taste all the flavors of Puerto Rico! The food in San Juan is some of the best we’ve ever tasted. From fine dining to local fare, this area has some of the best cuisine in the world. Be sure to indulge in local pastries like Mallorca and quesitos and traditional pinxtos like alcapurrias and bacalaitos.

For our most recent trip to San Juan, we decided to stay at La Concha. Take a look at our fun-filled, 48 hours in PR!

Saturday

9am We flew in early Saturday morning from NYC and arrived at our hotel. The room wasn’t ready yet, so we grabbed a café con leche and quesito from Aroma café and headed around the corner to Ventana al Mar, a park on the ocean, to enjoy breakfast with a stunning view.

Noon Dropped our stuff in the room and changed into our swimmers. Headed out to find a bite to enjoy on the beach and stumbled upon the hip food truck La Cocinita. Feeling hungry we ordered everything – alcapurrias, bacalaitos, queso frito (fried cheese with a guava dipping sauce) and shrimp tacos! The food was authentic PR street food made with love and we’re still salivating over it! We spent the next few hours sipping rum cocktails soaking in the sun on Condado Beach.

5pm After a quick refresh and outfit change, we headed out for a pre-dinner margarita at Tijuana’s on Ashford. Be forewarned, their margaritas are large and strong!

7pm Dinner at Cocina Abierta. Using locally sourced ingredients, the team prepares a mélange of Caribbean flavors. We loved the Red Bean Soup with sweat potato foam and the fresh speared local white fish (caught that morning) marinated in tamarind and turmeric on a bed of farm-fresh veggies. The wine list is unique and carefully curated – the Moscatel from Spain is a must! Our server Camila was an absolute delight.

Sunday

9am Grabbed bikes from the hotel and rode around Condado. Explored the beach and neighborhood along the way with a smoothie from BaJuice on Ashford.

Noon Strolled around Old San Juan seeing the umbrellas “sombrillas” by La Forteleza and made friends with the many cats on Calle del Cristo. Wandered around the old city exploring the plazas and discovering the murals and amazing architecture.

2pm Enjoyed craft beers and snacks at La Taberna Lupolo.

5.30pm Sunset sail around San Juan Bay with Sail PR.

8.30pm Dinner at La Casita Blanca in Santurce. Wonderful traditional Puerto Rican cuisine in a warm, inviting environment with the kindest family service. The bacalao guisada is a must. Be sure to snag a bottle of the Pique (homemade hot sauce to take home with you!)

10pm Dancing in La Placita de Santurce. Best night ever.


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