In late 2017, Hurricane Maria tore through Puerto Rico and Dominica, leaving the large majority of the affected areas totally devastated. San Juan and surrounding communities have begun to bounce back, while the entire island is still struggling with the destruction in the wake of the storm. More than a year later, economists have estimated a$43 billion dollar economic impact, entire communities in southeast Puerto Rico are still struggling with housing and basic infrastructure needs, and nearly 4% of the population has actually left the island in hopes of finding a better quality of life.
When I was invited to travel down to Puerto Rico last month, I confess, I had an initial hesitation — not because I was concerned about my safety, or because I was averse to witnessing the aftermath of Maria, but I thought to myself, “Is this really a trip I want to recommend to my readers and followers right now? Is Puerto Rico ready to support the type of tourism that is needed for them to continue on the road to recovery?” But, then I remembered how eager I was to see San Juan as the thriving community I had heard it to be from friends & family who had visited pre-storm. The stories of community, generosity, and kindness superseded that of worry and devastation. Less than a day later, I confirmed the trip.
A few weeks later, I hopped a direct flight from Boston to San Juan (JetBlue flights are as low as $133 right now) and found myself in Old San Juan, surrounded by color, smiling faces, and countless corners to explore. For the trip, home base was the Hotel El Convento, a renovated convent with a storied past, in the middle of the city. The property boasts cheery yellow walls, exposed mahogany beams, a courtyard perfect for lounging, and welcome drinks that will put even the weariest of travelers in a good mood. Their suites are expansive, and the rooftop plunge pool overlooking the city certainly didn’t hurt either.
On subsequent days during our trip, I also had the pleasure of exploring the Condado Vanderbilt (including a spa appointment that was top notch) and La Concha Resort & Spa. If you’re looking for accommodation situated on the beach, either of these make an enjoyable option. As an added bonus, the Condado Vanderbilt also is home to one of the tastiest dinners on the island courtesy of 1919 Restaurant. Their poolside dining is also quite delicious, giving you an excuse to not move from your beach chair all day long, if you so desire.
Outside of the hotels, dining options abound in San Juan, and I encourage you to put your ‘foodie’ hat on and take part in the many culinary adventures that await. So many of you kindly reached out to me prior to my trip to recommend tasty spots (thank you!), but the restaurant that kept coming up was Marmalade, and for good reason! Getting a reservation can be tough in the high season, so be sure to plan ahead, but just like many of you, I couldn’t recommend this dining experience highly enough. Don’t leave without trying the white bean soup, and if you are vegan or vegetarian, be prepared for so many options that are rarely found in restaurants of this caliber.
If you’re looking for something a bit more low-key than Marmalade and 1919 for dinner, you can eat your way through all the Puerto Rican classics at Lote 23, a gastronomic oasis located in San Juan’s art and music district known as Santurce. Essentially, you make your rounds from stand to stand eating that proprietor’s prized dish. Send your friends out on a mission to collect what they think the three tastiest items will be (including drinks!), and come together for a smorgasbord that is simply satisfying. Everything I tried was delicious, so you really can’t go wrong!
What would vacation be without a few cocktails? A must have for drinks is Santaella – a local hot spot that hosts a cool crowd even on week nights. Don’t leave without trying the Tamarind Margarita, and one of their many tasty desserts. La Factoría is also an institution that cannot be missed. The multi-room bar has been dubbed one of the world’s top 50 bars, and is home to the famous Lavender Mule. Have a few for me on your visit, and stay for dancing until the wee hours.
For my final night, I enjoyed a few drinks at La Factoría and made my way back into my comfy bed at the Hotel El Convento before waking up early to wander around Old San Juan with my camera for a few hours. Below, see just handful of about 100 photos that I took, and loved, from my meanderings in this historic part of town.
After just a couple days on-island, it’s clear: Puerto Rico is poised for a serious comeback. San Juan was absolutely thriving, and deserves to make it onto your travel list for 2019. The friendliness of everyone I encountered on my trip has me already craving to go back! I genuinely feel like I’ve made great friends, and was so thankful for all of their guidance and recommendations for a memorable stay in their community.
Have plans to make your way to San Juan or other parts of the island next year? Let me know if the comments.
Venture travelist 
Wonderful article! My wife and I are going on vacation in 2 weeks. We are already rent a car and found a good hotel. This will be our first trip and I think this holiday will be unforgettable!