Striking architecture, brilliantly colored buildings, awe-inspiring Caribbean vistas, and a vibrant culture best describes Old San Juan, the oldest city in the U.S. and its territories. And when it comes to retail, its centuries-old blue cobblestone streets are lined with an enticing array of unique stores that can only be found in this enchantingly historic neighborhood.
Whether you’re looking for the perfect gift for a loved one or a colorful memento from an unforgettable trip, you’ll find it all in the Old City.
Puerto Rico’s intrinsic beauty has inspired artists for centuries, and many shops throughout Old San Juan, most on our list found on Fortaleza Street, highlight the work of local artisans. Stepping into Puerto Rican Arts and Crafts art gallery is like being engulfed in the imaginations of some of the island’s most creative residents. Operating out of a restored Spanish colonial home for more than 40 years, the shelves here feature treasures like Roberto Maldonado’s hand-carved wooden Pica horses, colorful carnival masks by Ponce’s Miguel Caraballo and coconut crafts from Francisco “Panchi” Tirado.
A short stroll away on Fortaleza Street is sister shop Mi Pequeño San Juan which sells hand-painted miniature replicas of San Juan’s colorful buildings and distinct doors, which can be personalized with names and addresses for a truly one-of-a-kind souvenir.
By turning self-replenishing bamboo fields into crazy-soft bamboo fabrics, Cariloha offers an exclusive collection of bedding, apparel, active wear, bath goods, and accessories made from soft, cool, clean and green bamboo. Cariloha San Juan is located in 258 Fortaleza Street.
Fans of Latin tunes flock to Fundacion Nacional para la Cultura Popular, a center that honors the contributions of Puerto Ricans made to music, dance, television, theater, and film. This non-profit also found on Fortaleza Street serves many functions – it’s a museum, performance space, dance and music school, and an archive. The 300 year old building also includes a retail arm that sells music on CDs, vintage vinyl (LPs), and DVDs by celebrated local artists in every genre, from Jose Alfredo Mendez, Luryanne Villegas, and Glenn Monroig among others. Signed posters of El Gran Combo, Tito Puente, and Willie Colon embellish the wall.
If you are a cigar aficionado then a visit to the Cigar House on Fortaleza Street is a must-do. This shop is the biggest cigar emporium on the island. Enjoy a fine cigar joined by a whiskey or aged rum in air-conditioned comfort. If you want something to eat, the owners don’t mind you ordering food from an outside venue and eating at the cigar bar. The Cigar House has more than 300 brands from around the world and is kept in a large walk-in humidifier including fine quality Dominican cigars and a variety of brands using Puerto Rican leaf. The Spanish owners live upstairs and if downstairs at the shop, take the opportunity to converse with them since they are extremely knowledgeable about the products. Imagine, they are also close friends with Arturo Fuentes, owner of one of the best rated cigar brand in the world, who recently visited the shop.
The home of Coqui el Original, an endearing line of charm bracelets, cufflinks, and accessories inspired by Puerto Rico’s resident resonant coqui frogs, N. Barquet Joyero on Fortaleza Steet also features collections from Spain’s Carrera y Carrera, Italy’s Garavelli Gioeielli, and other world-renowned designers.
Pandora, a Danish designed brand world known for its hand-finished, contemporary pieces like charms, rings, earrings, necklaces and fashionable bracelets; sells items made with ethically sourced gold, sterling silver and rose metals. Its bracelets’ modular design allows customers to change the beads to dress them up for an elegant look or for a more casual wear at a moment’s notice.
For gifts that impress without breaking the bank, Blue Diamond on Fortaleza Street stocks duty-free jewelry at three locations, including an outlet store for even deeper discounts. Customers can enjoy a refreshment while gazing in awe at the most luxurious selection of diamonds, jewelry, and watches. Diamonds International also keeps its prices reasonable by cutting out the middle man and sourcing its gems directly from its own mines. The duty-free store, which began its business in the Caribbean over thirty years ago, is particularly popular for its patented Crown of Light cut, where a startling 90 facets create a brilliant sparkle that will make any jewelry fan swoon.
To dazzle and delight, purchase a timeless treasure that recalls the glittering, sun-kissed seas of San Juan’s harbor. For twenty years, travelers with a keen eye for exquisite watches and jewelry have been returning to Club Jibarito on Calle del Cristo, the island’s exclusive retailer for an array of elite brands like Vacheron Constantin. The beauty of its products, the magic of the place, and the friendliness of the staff creates a memorable shopping experience.
An entirely distinctive style of Puerto Rican wares is available at The Poet’s Passage art gallery on Calle Cruz. The multi-use venue engages customers with eye-catching pieces from local artists, including inspirational posters by owner Lady Lee Andrews and depictions of Old San Juan by her husband, French painter Nicholas Tomassin. Exuding a warm and welcoming atmosphere, the space also hosts poetry readings, movie nights, and other community-building events.
Every epic shopping excursion includes a chance to rest your legs and fuel up, and Old San Juan offers no shortage of delectable spots to grab a mouthwatering bite. To cool off and satisfy your sweet tooth, visit Chocolato on San Francisco Street for a scoop of creamy Italian gelato, and put a big smile on your face or swing by ice cream shop Señor Paleta on Tetuan Street, where the freezer is stocked with homemade artisan gelato and sorbet popsicles in deliciously creative flavors like guanabana (soursop), strawberry mojito and chocolate brownie, among many others.
To add some Puerto Rican spice to your own cooking, stop into Spicy Caribbee on Cristo Steet. A can’t-miss store for culinarians, the shelves here overflow with inventive bottled concoctions inspired by the Caribbean like banana ketchup, mango-pineapple jam, and spicy guava salsa, just to name a few.
Feeling the heat? Shade yourself from the San Juan sun with a trip to El Galpon. A staple in the city for 22 years, this intimate outpost on Calle de Cristo features authentic handmade Panama hats sold by Gustavo Lerner and Betsy Garcia from a specific variety of palm tree called toquilla that grows in Ecuador. The shop’s classic statement pieces are internationally lauded and have been featured on the runways of New York Fashion Week, loved by editors, celebrities and influencers across the globe. Complement your purchase with a guayabera shirt from La Casa de las Guayaberas on Tanca Street. Distinguished by their four pockets, vertical pleats and side slits, these traditional Cuban garments are designed for keeping cool in the Caribbean heat.
There’s no better place to find handmade tote bags than Concalma on San Francisco Street. The inviting brick and mortar store sells 23 different shapes and styles in eye-catching fabrics designed by founder Matilsha Marxuach, all of which are manufactured at an industrial women’s coop in Utuado in central Puerto Rico. For a more varied selection of goods you can feel good about, Eclectika on O’Donnell Street showcases Fair Trade-certified products from all over the world. Across the street, the tables that line the perimeter of Plaza De Colon offer the chance to interact directly with the artisans that create souvenirs ranging from ornate jewelry to blown-glass trinkets.
When evening nears and stores ring up their final sales, celebrate a successful day of shopping with a drink or an island-flavored gourmet meal at the charming La Casita de Rones on Darsenas Street. Sip authentic Puerto Rican rum at one of its two bars as you immerse yourself in the sweeping, scenic views of the harbor. Like what you’re tasting? Make your final purchase of the day a bottle or two to bring home.