Weekend Trip: 4 Days in San Juan, Puerto Rico
Right as I stepped off the plane and onto the jetway, I could feel the humid air hit me. This is the first time I’ve been back to San Juan since January 2022, and this time it’s for the WITS (Women in Travel) Summit. I guess I’ll use any excuse to come back to Puerto Rico!
I checked into the Caribe Hilton Hotel located on a small peninsula between Condado and Old San Juan. It was an easy, central location for the conference itinerary and off-site activities or other fun we had planned among friends attending too. Here’s a quick guide with top recommendations for a long 4-day weekend in San Juan, Puerto Rico:
Thursday
After arrival, we went straight to Old San Juan, where we took The Spoon Experience: Old San Juan Walk & Taste Tour™, a great food tour recommended by our conference organizers.
We had a lovely guide named Lorna who’s spent years in the media industry. Now she has a second career in guiding us around the cobblestoned streets of Old San Juan. She does it so well! We made a few stops as we learned about the history — and of course, photoshoot stops along the colorful architecture and the infamous umbrellas floating above Fortaleza Street.
First stop, dessert. Chocobar Cortés is much more than a chocolate shop. It’s a fourth-generation family-run establishment that has been funding arts education programs in the Caribbean. Located above the shop is an unassuming art gallery run by their non-profit Fundación Cortés. We sat below and bit into our sweet cocoa pastry treat, then washed it down with a Choco Frio - a chocolate martini that was incredible.
Then we dropped by a local female-owned restaurant called Juanes. We tried the local fare, a plantain mofongo, and washed it down with the local beer, an ice-cold Medalla.
After lunch, we went to the historic Hotel El Convento, a small luxury hotel with a lovely Spanish Colonial courtyard. Tucked inside is Patio del Níspero, the hotel’s lovely open-air restaurant, and above it is Santísimo Restaurant, another great stop. Pro Tip: If you want to book with a travel advisor, I can get you some special perks at this hotel in Old San Juan.
On our last stop, we walked over to Calle San Sebastián, a lively street with a lot of great bars, and headed to La Cubanita, which is one of six bars connected to La Factoría, named the Best Caribbean Bar this year by World’s 50 Best Bars. We indulged in one final drink: the Piña Colada, the ubiquitous classic cocktail invented in Puerto Rico. We parted ways with our larger group and I took a few of my friends through a door to the many speakeasy-style bars behind. My friend took us last time so I knew my way around but it made me look like a super insider!
Friday
The following day the summit was in full swing with meetings, and sessions. After, I met my friends who live in Puerto Rico at Luisa Restaurant, which had a hopping local bar scene. We then closed the day out with an event hosted by Discover Puerto Rico at the new Distrito T-Mobile, a destination for all sorts of entertainment and dining.
Saturday
While Saturday rolled around and the full day of sessions continued, the weather was not cooperating, so I wasn’t missing much pool time, thankfully. As the last session started, we snuck out to celebrate Katie “Traveling Spud’s” birthday (we met in Lebanon on a Wander Women Retreat!) at a local hotspot Santaella in Santurce. It’s not an easy reservation to get so definitely book ahead! The cocktail menu and food were incredible.
JungleBird, a great indoor/outdoor tropical cocktail bar, is right across from Santaella. We sat outside and had drinks there - highly recommend it! After our joyous backyard vibe, we changed it up to a more outdoor party vibe and spent some time at La Placita de Santurce, located just a few steps away. “La Placita” is a produce and food market founded more than 100 years ago and while it still functions as a market during the day, at night it transforms into a nightlife hot spot beloved by locals and tourists alike.
Sunday
For my last night, I got to get together with the incomparable luxury hotel queen Michelle Burn from St Regis Bahia (where we stayed last visit.) She took me back to Distrito T-Mobile to sample food from a renowned Puerto Rican chef at La Central by Mario Pagán. Indulging in a few cocktails, caviar, and oysters, we had ourselves a fabulous girls’ night.
On Sundays a lot of places may be closed so be sure to plan out your reservations ahead of time so you don’t miss out. Distrito was a great option for Sunday and was very busy with people of all ages, and families enjoying the many options there.
Every time I leave Puerto Rico, I come to the conclusion that I need to add more time to get further afield to El Yunque, Vieques, and more. On my first visit, I did end up in Rincón, a surfer town on the west side of the island, but on the next visit, a longer road trip, and island-hopping will be in order. Cheers!
Looking to visit San Juan, Puerto Rico? For your hotel needs and trip ideas, get in touch!
