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In recent years, San Juan has been in the throes of a renaissance. In the wake of 2017’s devastating Hurricane María, the city’s palpable spirit of resilience and recovery reached a dazzling crescendo in 2022 when the city celebrated its 500th anniversary. Visit the Museo de San Juan for exhibits and art that trace the island’s history from the Caparra ruins to modern-day neighborhoods.

The outstanding Museo de las Américas stands as a testament to the historical importance of the second-oldest European settlement in the New World (only Santo Domingo in the Dominican Republic is older). Evocatively housed in former military barracks, the museum’s well-curated displays chronicle the island’s rich African heritage, indigenous culture and tumultuous colonial period in thought-provoking ways.

Planning tip: San Juan's other top museums include the Museo de Arte de Puerto Rico (MAPR), containing over 4000 artworks spanning the 14th through 19th centuries, the Museo del Mar for nautical history, and the Museo de Arte Contemporáneo, featuring 1200 Latin American, modern Caribbean and diaspora artworks from the mid-20th century to the present.

Small but perfectly formed, Old San Juan is a historical repository of beautifully preserved colonnaded buildings, historic plazas and streets cobbled with ballast from Spanish galleons. Walls from the 16th century enclose a seven-by-seven grid of streets that brim with flower-filled patios, eclectic boutiques, contemporary art galleries and a handful of engaging museums.

Two strategically positioned fortresses – built by the Spanish to thwart buccaneering Brits and Danes – guard the bay like giant sandcastles plucked straight from a child’s picture book. A surfeit of architectural showpieces includes the venerable Gothic-style Catedral de San Juan Bautista, built in 1540, and the palatial fort of La Fortaleza, the eye-catching official residence of Puerto Rico’s governor.

Planning tip: Old San Juan is easy to get around on foot, but if you're planning to go farther afield, you'll probably need to take a ride with a taxi, the free trolley or the inexpensive bus network.

Built over the span of two centuries to repel Puerto Rico’s seaborne aggressors, El Morro – the city’s crown jewel – kept the Spanish flag flying over San Juan for almost 400 years until American troops poured into the city in 1898.

Majestically rising above the northwestern point of the Old San Juan peninsula, this 16th-century site became a national monument in 1961. El Morro towers 140ft (43m) above the Atlantic Ocean and forms a fascinating labyrinth of dungeons, vaults, barracks, turrets, lookouts and secret passageways. Ringed by walls that top 45ft (14m) in places, these fortifications came close to bankrupting the Spanish crown, which funded their construction.

Planning tip: Head here on weekends when local families flock to the fort’s grassy promenade to picnic, walk their dogs and fly kites – you can buy your own kite from the vendors in front of the site.

One of San Juan’s must-visit cocktail bars, rejuvenated the city’s bar scene when it opened in 2013. Now La Factoría is an international phenomenon, thanks in no small part to being the music-video location for the iconic reggaeton hit “Despacito”. Graffiti-etched passageways link to a chic lounge, a sultry wine bar and a salsa dance floor.

The common theme is terrific music and virtuoso mixology. A house favorite is the Lavender Mule, a potent combination of house-made ginger beer and lavender-infused syrup.

Dubbed the “Avenue of the Arts,” Calle Loíza overflows with stylish cafes, eclectic restaurants and concept stores that channel Puerto Rico’s #apoyololocal (shop local) movement.

The collaborative zeal and resilience of Loíza’s female entrepreneurs have defined the island’s recovery post–Hurricane María. In the space of several blocks, you can peruse the ocean-inspired dresses of former Allure editor and San Juan native Tanamá Besosa Castillo at ; savor a robust cortadito coffee made with locally produced beans at Café con Cé; and rejuvenate with a tropical-fruit smoothie at Kamoli Juice Bar. Pause at , built around bright yellow shipping containers, for a casual alfresco lunch of classic Puerto Rican bites and international fusion fare.

Art is everywhere along Avenida de Diego and Calle Tapia. One of the area’s most emblematic artworks, Loíza Brinca by local artist Abéy Charrón enlivens an entire building with the Puerto Rican flag. On the corner of Loíza and Benitez Castaño, check out the bold, geometric mural by up-and-coming local design studio Kiik Create.

A stone’s throw from La Placita de Santurce, José Santaella’s is a trend-driven, fun place to try contemporary Puerto Rican cuisine. Located inside a former hardware store, the spot has an industrial decor that contrasts with flamboyant tropical murals and Caribbean dishes that fuse authentic local flavors and international cooking styles.

There’s plenty on the menu to satisfy vegetarians, pescatarians and meat lovers alike. Try the succulent jumbo shrimp drizzled with a garlic cream sauce or the sashimi-grade ahi tuna skewers that are perfectly spiced.

The signature trifongo adds yucca and sweet plantains to the traditional mofongo recipe (fried green plantains mashed with meat or seafood) and is one of the best items on the menu. Farm-to-table roasted cauliflower and butternut squash come served atop feta cheese labneh and almonds.

At the sleek bar, mixologists craft tropical libations and inspired interpretations of classic cocktails – local favorites are the Sandía Mojito (made with watermelon) and the tequila-infused Espresso Martini.

The revitalized neighborhood of Santurce bursts with color and creativity; the hub of this rapidly gentrifying barrio is La Placita, a historic farmers market by day and vibrant outdoor party by night.

Come evening, office workers swing by, groups of friends spill out onto the streets and families gather at the many bars and restaurants that surround the square. From 10pm onward, everything kicks up a notch, as musicians take to the makeshift stage and spirited salsa and perreo dancing takes hold.

Planning tip: Come for the long-haul as this is not a short party – invariably, the revelry continues until dawn.

Surfers of all stripes are drawn to San Juan’s consistent swells, diverse breaks and laid-back vibe. Perched on the northern end of Puerta de Tierra, just outside Old San Juan, Playa Escambrón – known locally as La Ocho – is considered San Juan’s best balneario (public beach).

Escambrón combines dramatic scenery with family-friendly recreation and amenities. Beautiful palm-shaded sands are protected by a coral reef which provides rewarding snorkeling opportunities at Escambrón’s namesake marine park. Snorkelers can float among schools of blue tangs and damsel fish that carouse magnificent brain coral. (For prime marine life viewing and visibility, aim for the western side of the conspicuous rock offshore.)

Planning tip: Worth a visit nearby is the Batería del Escambrón (Escambrón Battery), a small 18th-century fortification, and the oceanfront Parque del Tercio Milenio, a popular green space peppered with trails and bike paths.

A short ferry and taxi ride from the main islet of Old San Juan is Casa Bacardí, the rum giant’s flagship factory and spiritual home since the Bacardi family fled from Cuba to Puerto Rico in 1936.

The largest of its kind in the world, the distillery produces a staggering 100,000 gallons of rum each day. The Bacardi Visitor Center (included with each tour) is a must-see – its “cathedral of rum” interior, designed to reflect a Cuban villa, houses an interactive history of both the company and rum that includes a film, audio guides and the opportunity to nose rum ingredients.

Planning tip: Bacardi offers three tours: a rum tasting tour ($75), a mixology session ($75), and the legacy tour ($30) that focuses on Bacardi family history. Be sure to end your visit with a cocktail on the waterfront pavilion with views of El Morro.

Head out of bustling San Juan to experience Puerto Rico’s dramatic topography on a day trip to the foot of the island’s highest mountain, Cerro de Punta.

Hacienda Pomarrosa is a family-run specialty coffee farm that operates daily tours of its plantation within peaceful, panoramic surroundings. Owner Kurt Legner and his son Sebastian guide visitors through the history of coffee (with tastings) and lead an informative walk around the vibrantly green coffee-growing areas. The tour concludes by heading to the various production floors before rounding off with another exceptional brew.

Planning tip: Coffee tours run daily Monday to Saturday from 11am to 1pm; advance reservations are required.

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