Explore San Juan in 48 Hours: The Ultimate Weekend Itinerary
Day 1 - Arrival
Upon landing in Puerto Rico, your first destination beckons with a blend of history and luxury: the Hotel El Convento in Old Town San Juan. This storied hotel, originally a Carmelite convent more than 370 years ago, offers an immersive experience into the island's rich past. As you step into the hotel, you're greeted by beautifully restored Spanish Colonial architecture, creating an ambiance of timeless elegance. Each room is a gateway to the past, adorned with exquisite antique furniture that speaks volumes of its historical significance.
The hotel's crowning jewel is a 300-year-old Nispero fruit tree, standing majestically in the original courtyard, a living testament to the enduring legacy of this enchanting place. The service at Hotel El Convento is as remarkable as its history, ensuring a stay that combines luxury with a personal touch. Mornings are greeted with a delectable breakfast menu, offering a taste of local flavors and culinary traditions. This historic haven is not just a place to stay; it's the first chapter in your Puerto Rican adventure, a haven where history and hospitality intertwine to provide an unforgettable experience in the heart of Old San Juan. Here is their Instagram to get some photo inspo!
Night 1 Dinner Options
I have two recommendations for your first night in PR.
Option 1: Indulge in the rich flavors of Puerto Rican cuisine at Deaverdura in Old Town. This is an understated spot for authentic mom-and-pop-style Puerto Rican cuisine. Known for classic Rice, Beans, and slow-cooked meat. As a vegetarian I was served a green plantain pastele which is similar to a Mexican tamale.
Option 2: Bacoa, located a mere 45 minutes from San Juan, Puerto Rico, stands out as a culinary gem, embodying the essence of farm-to-table dining. On my recent visit, the experience kicked off with a delightful three-dip appetizer featuring pumpkin, beet, and classic hummus, ccompanied by irresistibly crispy rounds enhanced by homemade ketchup. The freshness of the octopus ceviche was a highlight, beautifully complemented by an assortment of salads - watermelon, cucumber, and a classic Caesar.
The invitation to step into the kitchen was an exciting peek behind the scenes. Bacoa's signature barbacoa cooking style, which involves open flame grilling, brings an unmatchable freshness to the dishes, served right at your table. The waiter prepared a citrusy, chimichurri-topped dish that was simply sublime. The lamb, as suggested by my companion Colin, truly 'stole the show' with its rich flavors. To top off the meal, the bread pudding and cheese flan were divine, making my dining experience at Bacoa nothing short of a perfect 10 out of 10.
Night Cap
Back in the Old Town, unwind with a tantalizing Passionfruit Mojito at Pira Rum, immersing yourself in the local nightlife. This is a cute and lively bar just across the street from the Hotel.
Day 2 - Surf & Food Tour
Greet the next day with an invigorating surf class at @wowjetski. Whether you opt for a group session or a private lesson, the experience is bound to be exhilarating. We met up at 10 AM for a private lesson. The instructors at this small surf school are extremely experienced in surfing as well as have grown up surfing in the waters you will learn in. This gave me an added layer of comfort going into the class knowing I was in good hands. We learned the basics in the sand before getting right into the waves. My instructor swam/stood in the water holding my board and selected the waves for me to attempt to surf. I was standing by my second wave and by the end of the class we even attempted some larger waves farther down the beach. Any time you learn something new you can expect to be tired out! Reserve some time to relax and sunbathe at the serene Isla Verde Beach after the class.
I booked a culinary journey led by @thespoonexperience through Old Town on the Sunset Walk & Taste Tour. We had four stops on our tour ranging from dessert to cocktails to full plates of food. As a vegetarian they did a great job at accommodating my preferences but, as I’ve noticed in many Caribbean islands, the love that goes into food is often in the meat and fish. My favorite dish on the tour was at the final stop. Don't miss trying the Mofongo at @juanes.restaurant, a personal favorite. The tour guide was great and she sprinkeled in a lot of history and fun facts about the Historic Old Town as we went.
As your day in Puerto Rico draws to a close, there's no better place to immerse yourself in the island's vibrant nightlife than at La Factoría in Old San Juan. Celebrated as the Best Bar in the Caribbean in 2023, La Factoría offers an enchanting maze of seven different bars, each promising a unique atmosphere. Step into this rustic, unmarked gem and wander through its secret passages, discovering a world where Puerto Rican mixology is elevated to an art form. The ambience is electrifying yet cozy, combining low-lit settings with the invigorating rhythms of salsa. Masterfully crafted cocktails, such as their signature drink, are refreshingly simple yet skillfully made, ensuring every sip is a memorable experience. Whether you're a cocktail aficionado or simply seeking a lively spot to unwind, La Factoría's blend of exceptional drinks, charming ambiance, and friendly service makes it an unmissable destination to cap off your night in San Juan.
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