A Foodie’s Long Weekend in Puerto Rico

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Advisor - Savannah Dempsey
Curated By

Savannah Dempsey

  • Puerto Rico

  • Arts & Culture

  • Beaches

  • Foodie

  • Long Weekend

  • Local Culture

  • Local Food

Sculpture cat chairs in San Juan, Puerto Rico with Advisor posing in a hat on a sunny day.
Curator’s statement

Puerto Rico offers a culinary adventure like no other, seamlessly blending rich cultural heritage with modern innovation. This guide takes you through the island's vibrant food scene, from traditional cooking classes and delectable street food tours to luxurious farm-to-table dining experiences. Embrace the local culture, support sustainable practices and indulge in a foodie paradise that’s as diverse as it is delicious. Tip: This would make the perfect long weekend before or after a cruise!

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Where to stay in Puerto Rico

Hotel El Convento

Long-time favorite in Old San Juan, with a traditional look and access to a sister beach club.

Fora Perks
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    $100 food / beverage credit.

  • ★

    Breakfast daily.

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    Upgrade & extended check-in/out whenever possible.

Casablanca Hotel

An enchanting blend of timeless elegance and modern luxury set in a historic building, offering you an unforgettable stay.

Dreamcatcher By Dw San Juan Hotels

Dreamy San Juan bed and breakfast with fun, hippie-style lodgings and excellent breakfast perfect for an adventurous and edgy kind of traveler.

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Things to do in Puerto Rico

Explore the city by taking a walking tour.

  • Walking Tours: I always recommend walking tours on day one with a local. This is the best way to get a feel for the city, get the best tips and support the local economy!

  • Food Tour: Experience Puerto Rico’s cuisine while wandering cobblestone streets, learning about gastronomy, history and architecture. Mofongo guaranteed!

  • Cooking Class: Learn how to cook a traditional Puerto Rican meal with local, Yeira.

  • Swim with Bioluminescent Plankton in Mosquito Bay: The best place to view the island, and one of the few places you are permitted to swim with the plankton.

  • Wander through The Poet’s Passage: A local art store focused around poetry and painting. Check out their open mic nights.

  • Rent a Boat Out East in Fajardo: Explore Puerto Rico’s top islands: Culebra and Vieques.

  • Relax on the Beach: Condado Beach (luxe and lively) or Escambron Beach (picturesque, snorkeling available).

  • Take a day trip west to Rincón.

Places to eat & drink in Puerto Rico

Wine-pairing dining in Puerto Rico.

  • Verde Mesa: Woman-owned and operated, farm-to-table ingredients sourced from local farms. The menu is ever-changing, creative and delightful. Save room for their famous Purple Cloud dessert.

  • Did you know: 89% of the food on the island comes from the US or further. Supporting farm-to-table in Puerto Rico is supporting locals to an extreme!

  • Deaverdura: Spectacular! Super local and popular among everyone who goes there! No menu. They just serve traditional Puerto Rican food and you choose your protein, vegan-friendly.

  • El Vino Crudo: Natural wine bar tucked away on a side street. Light bites and wine pairing recommendations. You can also grab a bottle to take to the beach.

  • Marmalade: Farm-to-table luxe dining. This is everyone’s top recommendation. Reservations required.

  • La Factoría: Multilevel bar with something for everyone. Speakeasy soft jazz in one room, live Spanish music and dancing in another.

  • The Cannon Club: Bar with live music, sometimes dueling pianists. There is dinner as well, but I recommend saving your food for another restaurant. Reservations required.

  • Chocobar Cortés: I wasn’t sure when I first peeked my head in. It is super casual and touristy, but my goodness! The food is delicious and they incorporate cacao in every dish.

Advisor - Savannah Dempsey

Travel Advisor

Savannah Dempsey

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This guide is part of our ongoing series on travel to Puerto Rico. Looking for more travel inspiration? Check out my guide, Icelandic Retreat: Serenity in the Land of Fire and Ice.