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13 Things to Do in San Juan, Puerto Rico: Our Ultimate Travel Guide

You may not need a passport to travel to Puerto Rico, but the island still feels worlds away—especially the capital of San Juan, with its pastel-colored buildings, flavor-packed cuisine, and steamy salsa music. If you're thinking of planning a trip there soon (or need 13 reasons to convince you to go), check out our ultimate guide to San Juan, Puerto Rico.

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1

STAY

Condado Vanderbilt

This oceanfront grande dame, originally built in 1919 by a Vanderbilt family member, sits three miles from Old San Juan and is a perfect base for splitting time between town and the beach. A $200 million renovation in 2014 brought in Puerto Rico’s first hammam and new pool lounge areas in addition to a refresh of its 219 rooms, many of which have balconies or terraces with sea views. Even if you don’t plan to stay, be sure to take a stroll along the property's oceanfront promenade followed by a four-course prix-fixe dinner at 1919, considered one of the finest restaurants in all of the Caribbean.

Hotel El Convento

This former 17th-century convent turned 58-room boutique hotel puts you in the heart of the city’s most atmospheric dining and entertainment district. Inside, old-world touches like beamed ceilings and terra cotta tile floors nod to the area’s colonial past, but the creature comforts are all decadently modern, including a private beach club, two stylish restaurants that serve Spanish-style tapas and Puerto Rican cuisine, and a rooftop plunge pool and terrace, where the city's style set comes to enjoy sundowner cocktails and views over Old San Juan.

The Ritz-Carlton, San Juan

You'll find this sumptuous Ritz-Carlton property sprawled across eight oceanfront acres on Isla Verde, six miles east of Old San Juan. Spend your mornings taking a surf lesson on the beach or playing the tables in the hotel’s casino before heading into town for a tour of historic sites and fabulous local dining. Otherwise, five onsite restaurants include an outpost of BLT Steak while the 12,000-square-foot spa has treatments inspired by the island’s El Yunque Rainforest. (JS Tip: Try the river stone massage.)

RELATED: The 10 Best Hotels in Puerto Rico

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2

EAT

Restaurant Raices

Every Puerto Rican and their brother will suggest you try out Restaurant Raices in Old San Juan. Heed their advice (and ours) and go. Here, it’s all about mofongo, a hearty, mashed, plantain-based Afro-Puerto Rican dish that's piled high in tall wooden bowls. The addition of flavors like mahi and shrimp guarantee it’s like none you’ve ever tried back on the mainland. The countryside hacienda-style décor and costumed servers add to the fun, as do the pitchers of sangria. For an affordable, authentic, and atmospheric dining experience, it’s an all-around winner.

1919 Restaurant

Despite prices that match the prestige of chef Juan Jose Cuevas at its helm (whose has worked at multiple Michelin-starred restaurants around the world throughout his career), 1919 Restaurant is worth the splurge for a meal you're sure to remember long after your table is cleared. An elegant dining room inside the Condado Vanderbilt Hotel with spectacular ocean views sets the stage for simple but elegant dishes like snapper crudo and longaniza (Spanish sausage), which use mostly locally sourced and artisanal ingredients. Book well in advance for both three-course lunches or four-course dinners and prepare to be wowed.

Cocina Abierta

The Condado crowds descend in droves on this open-kitchen restaurant with a big city vibe. Argentinean chef Martin Louzao takes a page from Puerto Rico’s multi-culti history to showcase the island’s diverse cuisine influences, which include European, South American, African, and Asian flavors. Try the catch of the day—fried tempura style—paired with a sea urchin beurre blanc and yucca purée or Bolivian rabbit stew with Andean potatoes.

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3

SEE

Old San Juan

Honeymooners, European backpackers, cruise ship passengers, Caribbean yachters basking in shore leave—you’ll find them all enjoying the 16th- and 17th-century Spanish colonial facades, cobblestone streets, forts, and bars that pack into the seven blocks that comprise San Juan’s atmospheric old quarter. Climb the 16th-century fortress, Castillo San Felipe del Morro, for ocean views, then refresh with a cold beer at a curb-side café.

Santurce

San Juan’s vibrant art scene plays out on the streets of Santurce, the neighborhood between Condado and Isla Verde, where colorful, edgy murals can be found on every surface—from dilapidated buildings to alongside highways. Head to Loiza Street, the main drag, and browse its countless casual little cafés, hipster bars, and vintage boutiques.

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Photos courtesy of Bar Gitano

4

DRINK

La Factoria

A bit old-world, a bit East Village, and a bit San Juan: that’s the mashup at this cult favorite cocktail bar in Old San Juan, known as much for its atmosphere—think old-school salsa, vintage furniture, and paint-peeling walls—as it is for its craft cocktails, which are on par with anything you’d find in a major metropolis (psst: try the lavender mule). The crowd is predominantly artists and musicians along with the occasional smug-looking tourist, proud that they’ve discovered such a find. Be sure you find your way to the wine bar, accessed via a hidden door (a red light bulb on the wall will indicate it's open for business).

La Coctelera

This gastro-bar in artsy Santurce occupies an industrial space on Loiza Street, and really comes to life at night. Come for the shared plates, which pair perfectly with innovative cocktails like the Tesla, a mix of vodka, gin, limoncello, tonic, and fresh lemon juice that you sip from a lightbulb with a straw.

Bar Gitano

For tapas, cold beers, and warm vibes, head to this Spanish tasca-inspired spot in Condado, defined by its exposed brick walls and busy outdoor terrace that's seemingly always packed with both tourists and locals. Snack on bacon-wrapped dates and chorizo while downing the excellent house-made sangria.

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Photos courtesy of Concalma

5

SHOP

Concalma

Unique backpacks, messenger bags, and beachy designer totes are among the fair-trade items for sale at this boutique in Old San Juan. The shop was opened by a designer after several island factories closed down. Their aim: provide a storefront for bespoke pieces made at an all-women factory in the mountains of central Puerto Rico.

El Alcazar

Caribbean antiques hunters flock to this cave of wonders of a shop on San Jose Street, one of the biggest antiques bastions in the Caribbean that's well-known for its 18th- and 19th-century European and Asian finds. Religious artifacts, original oil paintings, and one-of-a-kind furniture pieces are among the loot, collected mostly from estate sales in Puerto Rico and the mainland.

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