Tips + Trends

Got 3 Days to Spare? Tackle San Juan Like a Pro on a Weekend Getaway

Catch some rays and watch the surf roll in on Condado Beach. (Photo: Jessica van Dop DeJesus)

A short flight from many United States airport hubs, San Juan, Puerto Rico, is ideal for a tropical weekend escape. The island’s capital city is filled with innovative restaurants, lovely beaches and a good dose of Caribbean history. Take a break from your routine to eat local Puerto Rican foods, bask in the warm salty breeze and explore San Juan on a three-day jaunt.

Discover Old San Juan

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Discover the island’s past in historic Old San Juan. (Photo: Jessica van Dop DeJesus)

El Viejo San Juan (Old San Juan) is a popular place for locals and tourists alike. Established more than 500 years ago, it is one of the oldest cities of the New World. Wandering along the cobblestone streets of the old city and admiring colorful Spanish Colonial architecture is an experience in itself.

Take a self-guided tour of El Morro Castle, a UNESCO World Heritage Site. The fort has been carefully preserved and gives you a glimpse of how the Spanish protected themselves from foreign invaders.

Take a stroll down the romantic Paseo de la Princesa, a promenade that extends along the coastline of the old city. Here you’ll catch a glimpse of the profile of El Morro and, if you arrive in time, have a chance to watch the sunset as sailboats glide by on the bay.

Beaches of San Juan

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Chill out with an umbrella and cold drink along one of San Juan’s sandy shores. (Photo: Jessica van Dop DeJesus)

A trip to San Juan would not be complete without beach time. Sipping a cold Medalla beer while dipping your feet in the ocean is just what the doctor ordered — we promise. Ocean Park is a local favorite, packed with a young and stylish crowd.

The beach of the Condado neighborhood is also well-known, home to many of the popular hotels and resorts of the city. The Balneario of Carolina is a family-friendly stretch of sand with ample parking, picnic facilities and shallow water perfect for children to enjoy.

Where to Eat in San Juan

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Tuck into fresh seafood, like snapper with tostones, in San Juan’s restaurants. (Photo: Jessica van Dop DeJesus)

There are plenty of places to indulge in San Juan. For budget eats head to Piñones for lunch. This seaside neighborhood is lined with food stands that offer traditional treats such as empanadas, alcapurrias (green banana fritters filled with meat or seafood) and other decadent delights.

In Old San Juan, have a mallorca (a soft and sweet bread popular in Puerto Rico) sandwich at La Mallorca or indulge in the French Baguette Pudding at St. Germain Bistro and Bar. Visitors can also experience a traditional Puerto Rican farmers market at La Placita de Santurce.

Fine Dining in San Juan

Puerto Rico is currently undergoing a culinary renaissance with an increase in local agriculture. Try to splurge on at least one fine dining experience. Chefs have been diving deep into their roots and creating refined versions of Puerto Rican classics.

This can be seen at restaurants such as Santaella, Budatai and Pikayo, which have created elevated versions of revered Puerto Rican dishes such as roasted pork and local seafood and rice dishes.

Party in San Juan

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Toast to the good life in San Juan. (Photo: Jessica van Dop DeJesus)

Locals love a party. Bars and restaurants seem to have a perpetual happy hour punctuated by the beat of salsa music. Head to La Placita de Santurce from Thursdays to Saturdays to witness a street party as live music fills the air and people dance in the square and at surrounding bars. Many of the hotels in the area have live bands and DJs at their properties. If you’re eager to check out the bar scene, head to Old San Juan for craft cocktails in quaint bars such as La Fabrica.

If possible, plan your trip around Las Fiestas de La Calle San Sebastián (mid-January). What began in the 19th century as a celebration of Saint Sebastian has turned into a week-long celebration with live music in the city’s squares and thousands of people joining the party.

Shop, Shop, Shop

San Juan is home to the largest mall in the Caribbean, Plaza Las Americas. The mall has many of the shops you might see in a mall at home along with locally owned stores. Pick up a boho-chic dress at Hecho a Mano or locally made souvenirs at Arts & Crafts PR. For luxury shopping head to The Mall of San Juan. From Jimmy Choo to Ferragamo, it’s a glamorous shopping experience. Although Old San Juan is filled with many common souvenir shops, you can also find small shops specializing in handcrafted souvenirs and art such as Puerto Rican Arts & Crafts.

Take a Tour

There are many unique tours you can take in San Juan. See the city from above on a helicopter tour with Puerto Rico Helitours, take a relaxing boat excursion along the bay with Sail San Juan Bay, or gain a deeper understanding of the city’s culinary scene on a food tour such as Flavors of San Juan Tours.

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