Immerse yourself in Old San Juan
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Coqui, a frog native to Puerto Rico
DAY 1
Stroll the cobbled lanes, flanked by pastel-colored, classic Spanish townhouses and flower-laden patios, starting out on Calle San Sebastián. Take some time to peer into the niche boutiques and small art galleries spaced out along the popular street, which will carry you almost the whole way to San Juan’s fortified frontier. Castillo San Felipe del Morro, which has guarded the islet of Old San Juan since its construction started in 1539, feels as though it sprung from the rocks on Puerto Rico’s northern front, its historic walls whipped by the wind and stained the shade of the crag.
Start at La Fortaleza and climb between six levels of defensive walls to see where the Spanish fended off the Dutch, the English and slews of raiding pirate ships. Today, it’s the official residence of the governor of Puerto Rico, and it has been since the 16th century. The complex is large and multifaceted — take one of the regular tours run in English and Spanish, or lounge on its sloping lawn and watch as families gather to play impromptu games or fly kites.
Double back some 15 minutes to rest your legs at El Jibarito, a local favorite serving up traditional Puerto Rican dishes. Grab some pasteles (tamale-style mashed plantain and pork wrapped in banana leaves and steamed) or indulge in a side dish of mofongo (fried plantain mashed by hand) doused with garlic-laced butter.
Appetite sated, set out east to Castillo San Cristobal, the fortress that has flanked the other side of the old city since 1634. As well as offering its own fascinating military history, the castle is the best place to stop for a panoramic view over Old San Juan and its Caribbean Sea border. From there, head back into the bustle of the inner city along colorful Calle de la Fortaleza, with pit stops to window shop for local handicrafts, ornate jewelry and freshly rolled cigars.
Once the hunger hits again, Café Caleta is only a short walk away. A cafe by day and bar/restaurant by night, it serves up fresh fish ceviche-style, albondigas puertorriqueñas (spiced meatballs) and cured pork shoulder spiced with coffee. Add an accompanying nightcap — an evening in San Juan isn’t complete without the rich blended rum ever-present in Puerto Rico.
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The view from the San Juan Water and Beach Club Hotel
DAY 2
It only takes 45 minutes to drive from San Juan to the only tropical rainforest in the U.S. — El Yunque. Miles of accessible hiking trails weave through the mountainous terrain, which are bordered by dense thickets of towering tabonuco trees. The hiking routes range in difficulty, with options available for strollers and climbers alike. Take a short jaunt down the Angelito Trail to reach the rejuvenating waters of the Río Mameyes, then ascend the viewing platform on the 90-minute Mount Britton Tower route for panoramic forest vistas, or tackle the more challenging Los Picachos trail — it’s worth it for the vantage over the cloud-dusted mountain forest. Hikers hoping to push their limits should take the El Yunque Trail to watch the ecology shift with the altitude or the El Toro track to reach one of the highest points in the Luquillo mountains.
Refuel at El Yunque Rainforest Cafe, which is accessible by road, and which serves freshly fried empanadillas, tortilla-wrapped carnitas and smoothies blended with local forest fruits. After, explore the nearby waterfalls: La Mina, which cascades from 30 feet, is only a 10-minute walk from the cafe and has a cooling lagoon filled with recovering hikers at its base. Though slightly farther afield, in the south of El Yunque, it’s worth venturing to the La Canoa Falls to see the Taíno petroglyphs etched by the Indigenous peoples of the forest. Once you’ve tired of lofty treetops and orchid-dappled forest floors, drive half an hour to Laguna Grande to get ready for the best light show in Puerto Rico.
After pausing to crunch on deep-fried tostones (crisp plantain) dipped in garlic sauce or a comforting bowl of pollo guisado (traditional chicken stew) at a local restaurant in Fajardo, head out to the Laguna Grande to secure a kayak. Just before the sun sets, embark on a gentle paddle between the low-hanging boughs of the Red Mangrove Forest. It takes around half an hour to reach the Bioluminescent Lagoon, where every stroke of the paddle sets off a spiral of sapphire sparkles. Caused by billions of plankton swelling on the water’s surface, the ripple of a hand drifting in the water or the flap of a passing fish is enough to cast a mini “Milky Way” over the lagoon. Once you’ve paddled back along the glittering streams, head back to San Juan, around a 90-minute drive from Laguna Grande.
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A piña colada cocktail, which was invented in Puerto Rico
DAY 3
After an active day in Puerto Rico’s inland forests, it’s time to decompress. Recover on one of the sandy beaches surrounding San Juan. To stick close to the urban center of the city, head across the bridge from Old San Juan to the upscale, beachfront neighborhood of Condado. A laid-back spot teeming with lounging locals, it offers fine sands and gentle waves, alongside an array of seafront hotels, restaurants and bars. Dine alongside the Boricuas, as locals are known, at lunch at the unassuming Orozco’s, where the mofongo is mixed with octopus tendrils or generous chunks of lobster. Alternatively, opt for gouda and papaya croquetas and succulent sea bass at the sleek Mario Pagán’s. To add a final special experience to your weekend, book a table at 1919 ahead of time. Its five-course menu is designed by world-renowned chef Juan José Cuevas and features dishes like traditional Puerto Rican crudo topped with kristal caviar and poached lobster fresh from the San Juan shore. While away the afternoon with a creamy piña colada and lie on the soft sands that fringe the Caribbean swell — or head to the nearby Condado Lagoon, where it’s possible to spot manatees lolling in the waters. You can even rent a kayak here to paddle alongside the gentle giants. Alternatively, the district is home to San Juan’s main high-end shopping street, which has a selection of designer brands.
Afterward, head to La Placita de Santurce, which transforms from a farmers’ market to a social hub once the sun starts to set. It’s home to some of San Juan’s best cocktail bars — start at Asere Kitchen and Bar, known for its old-school Cuban ambiance and signature passionfruit and habanero mojitos. Stroll amid the art-adorned streets, dodging swirling salsa dancers congregating outside the chinchorros (inexpensive bar-restaurants), in the direction of La Penúltima. Sit with locals at their communal tables and sip on smoky toasted coconut scotch or mezcal mixed with sweet hibiscus. Once you’ve had a fill of island-inspired cocktails and mocktails, listen for the running rhythms of plena played on hand drums or the African-inspired beats of bomba — both Puerto Rican folk styles are heard every night in Santurce, home to an array of live music venues. It mingles in the evening air with the distant pulse of reggaeton, omnipresent on its origin isle.
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