Leave Your Passport At Home, We're Going to San Juan

Contributed By Kayla Douglas

A quick glance at a map of the Caribbean and sun-seeking travelers are left overwhelmed by dozens of options. And while there’s a unique vibe to each destination, this fall, our team was eager to experience island life beyond the beach. So, we left our passports at home, packed our sneakers and hopped the quick flight to San Juan.

Explore Old San Juan early in the morning to catch the streets with fewer tourists, which means more prime photo-ops for you

With the common misconception that Puerto Rico is still struggling to recover from Hurricane Maria’s vengeance last September, this trip was dual-purpose. Naturally, we wanted to check out the top hotels for our clients’ stay, but it was also our team’s mission to see how we could give back in some less conventional ways.

“The best way to support is to actually visit us,” says Carla Campos, Acting Executive Director for the Puerto Rico Tourism Company.

For this mission, we partnered with the Condado Vanderbilt Hotel as our local hosts and hit the ground running for a few days of packed activities. One thing to note, while we’re going to take you through some of the volunteer experiences we participated in while we visited, know that if you want to contribute to the long-term stability of this U.S. territory, it can be as simple as just showing up.

“The best way to support is to actually visit us,” says Carla Campos, Acting Executive Director for the Puerto Rico Tourism Company. “Spend locally, stay at hotels, eat at restaurants. We don’t need aid in the traditional sense anymore. We need the economy to flourish. Tourism is a sector that can enact change immediately.”

But first things first. Where should you stay?

Condado Vanderbilt Hotel

For travelers who want easy access to San Juan, we love the luxurious product available at Condado Vanderbilt. This Historic Hotel of America was built in 1919 and maintains its rich Spanish heritage nearly one hundred years later. You can feel the authentic vibes in the old-world gem the moment you step into its millennial pink lobby, opulence meets luxury.

We love this hotel for couples, families, and even larger groups as its expansive facilities (think: several restaurants, cigar lounge, great bars, etc.) can accommodate a wide range of needs. The adults-only pool located on the east side of the property is perfect if you’re looking to just zen out.

But if you have kiddos who want to splash around, don’t worry, there’s a family-friendly pool — plus smaller infinity pool overlooking the ocean — available at the opposite end of the hotel too. Or, if you’re simply eager to lay out at the beach, that’s not a problem either; the hotel offers Beach Club service to guests on the sand directly outside its gates.

The view from an oceanfront suite at Condado Vanderbilt
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Just be sure not to depart without scheduling some time at the spa, as you won’t want to miss out on a treatment at their impeccable facility. | Book Here

El Convento

If you’re looking for a more boutique property, then El Convento is just what you’re looking for.  We made it a priority to drop into this charming hotel in the heart of downtown Old San Juan, and was left completely swooning over its colonial charm.  El Convento is perfect for the active traveler who wants to be in the center of everything. It also happens to be a sister hotel to Condado Vanderbilt, meaning you can expect high-touch service and attention to detail, plus access to Condado’s Beach Club, fitness center and spa. Your room here will maintain some original fixtures from the convent-turned-hotel’s inception back in the 1950s, which will really have you feeling connected to the rich history. | Book Here

Voluntourism, please…

Puerto Rico is well-known for its diverse landscape; offering surfing, hiking, caves, bioluminescent bays, and the only subtropical rainforest in the U.S. But rather than crossing these items off our list (we’re totally going back to hit these outdoor activities!), we opted to check out some San Juan spots, as well as partner with local organizations to do our part in supporting the resilient communities of the island.

Toys for Tots

One of the projects that stemmed from the wake of Maria was bringing Toys for Tots to Puerto Rico for the first time.

With the holiday season right around the corner, it was the perfect time to get involved with a cause near and dear to the hearts of our hosts, Condado Vanderbilt. Over dinner during our first night on property, General Manager Ben Tutt shared stories about the hotel’s role in recovery last year; a recurring theme in these stories was human connection, particularly in the form of different governmental agencies and citizens pairing up to do whatever necessary to get the island back up and running. One of the projects that stemmed from the wake of Maria was bringing Toys for Tots to Puerto Rico for the first time.

With the manpower and investment of the U.S. Marine Corps, thousands of children were able to receive toys for Christmas last year. This year, they plan to impact even more children on the island. We were lucky enough to play a very small role in the sorting process as the Marines prepare for the toy pick-up, separating donations based on the best-suited age group. Our team had the best time helping out and getting a peek into this massive operation! If you’d like to learn more about this initiative or make a donation, check out the Toys for Tots Puerto Rico page.

Amigos de Los Animales Animal Shelter

After speaking to some Puerto Ricans about the challenges they face with increasing numbers of stray animals, our group was eager to spend some time at a local animal shelter. With initiatives like The Sato Project being a bit more widely known, we opted to check out a smaller organization, Amigos de los Animales.

Some of our Smarties with the Amigos de los Animales Rescue Animal Shelter team
Some of our Smarties with the Amigos de los Animales Rescue Animal Shelter team

Located in the Piñones beachhome of Shelter Director Adrienne Galler Lastra, they currently house about 70 dogs. In chatting with their team, we had the chance to learn more about the great work they are doing on the island. As a rescue organization and shelter, their mission is a big one, they’re looking to rescue, rehabilitate and find the forever home for the abused and abandoned animals throughout the island of Puerto Rico.

The shelter was incredibly hospitable in setting up time for a visit and during our time there, our team had the chance to help with a painting project and take some of the dogs out for some exercise along the boardwalk.

Walking the pups beachside with Amigos de los Animales Rescue Animal Shelter

We highly recommend giving Adrienne a call if you’ll be on the island and want to volunteer some time, but don’t blame us if you leave with a pup! Or, if you would like to donate to help support the shelter, check out their website for more details.

Playing Tourists

With only three days on the ground and most of our mornings filled with volunteering, we’re happy to report that we made some time to check out two of San Juan’s must-do’s, the Casa Bacardí Factory Tour and Old San Juan City Tour. Because when in Rome…

Casa BACARDÍ Factory Tour

Rum lover or not, a visit to the BACARDÍ factory makes for a fun couple of hours. The VIP tour included a private walk-through of the history of the facility as well as a mixology class. We learned some fancy bartender tips and tricks that we’ll certainly be showing off back home. With the technique down to make Cuba Libres, mojitos and daiquiris, we walked out with our official mixologist certificates!

Old San Juan

Our favorite “touristy” activity of the trip had to be wandering the streets of Old San Juan. Its colorful walls just beg to be photographed, so don’t expect to make good time when winding through the alleyways here.

Walk over to Fortaleza Street to check out the umbrella exhibit that was installed post-Hurricane Maria to help capture the vibrancy of the Puerto Rican spirit. Pro-tip: If you can make before 9am, you’ll have a better chance of beating the crowds (consider that it’s nearby the cruise terminal, making it a hot spot for day tours), whereas if you visit later in the afternoon you’ll get even better light for a photo or two.

Be sure to set some time aside to check out the two Spanish-built forts, too, so you can fill up on history. Or, do it like the locals and set up a picnic on the grass under a sky full of kites. With tons of great shopping downtown, you’ll want to be sure to catch a rest before meandering into the shops. We loved El Gapon on Calle del Cristo (just a couple blocks from El Convento) for their traditional Panama-style hats, fun handmade bags and colorful accessories.

Discover the colonial architecture of Castillo San Cristóbal
Discover the colonial architecture of Castillo San Cristóbal

Okay, so now that we’ve done all the things, what’s for dinner?

It was immediately clear upon arriving to Puerto Rico that we wouldn’t be leaving any thinner. From trying their notorious mofongo to sampling crispy pork belly — all before the main course — every bite was seemed to taste better than the last. Seriously, the food is so delicious you just can’t help but have one more. Every. Single. Time.

José Santaella

Imagine stepping foot in the buzziest restaurant in San Juan filled with a healthy mix of notable locals, in-the-know visitors and the most beautiful (sorry, we had to say it) staff. Got a visual? Dim the lights, add some Latin music and you’re in Santaella.

Expect delectable cocktails made by their award-winning mixologists to complete the vibe. Our hosts walked us through the menu and we truly left no stone unturned. Honestly, a reservation here is reason enough to visit the island.


For fine dining, it doesn’t get much better than 1919 Restaurant, located within the Condado Vanderbilt. Michelin Star-rated Executive Chef Juan Jose Cuevas believes in pairing social consciousness with exquisite taste.

His team hand-selects artisanal products to craft Puerto Rican cuisine with a contemporary flair. Here you’ll find how locally-rooted products pair with globally-sourced wine for world-class cuisine. Sommelier Alfredo Figueroa set up our group with varietals spanning from Napa to South Africa, with unexpected pairings like a Pinot Noir from New Zealand with locally-caught dorado fish. We loved every bite.

Tasting menu at 1919 Restaurant at Condado Vanderbilt
Tasting menu at 1919 Restaurant at Condado Vanderbilt

So, what are you waiting for?

In all honesty, San Juan took us by surprise. If you’re still hesitant to visit due to last year’s news cycle, we urge you to reconsider. The island couldn’t be more ready to welcome you with open arms. Just don’t forget to bring stretchy pants for the plane ride home.

Contact your travel advisor to begin planning your trip to San Juan.

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