iBestTravel has partnered with San Juan-based travel community Platea to provide comprehensive guides, curated lists, and insider tips for your next trip to Puerto Rico.
Puerto Rico is one of the most accessible tropical destinations for domestic US travelers. From the East Coast, you can hop on a flight after breakfast and have lunch with your feet in the sand.
San Juan serves as the hub for discovering la isla del encanto. Puerto Rico’s romantic capital is filled with historic landmarks, vibrant dance halls, and renowned restaurants. A three-day itinerary offers a perfect taste of this revitalized metropolis while allowing time to discover picturesque beaches and the island’s crown jewel: El Yunque National Forest.
Day 1
Morning: Tread the Cobblestones of Old San Juan
Fall under the spell of Old San Juan. This cultural gem boasts colorful Spanish townhomes, majestic forts, historic churches, and plazas, all surrounded by a largely intact 16th-century wall. Immerse yourself in the city’s charm with a stroll along Calle San Sebastián, overflowing with flower-filled patios and eclectic boutiques.
Enjoy brunch with locally sourced Gustos coffee at Mercado la Carreta. Continue your walk along Calle Norzagaray to the impressive Castillo San Cristobál.
No visit to Old San Juan is complete without exploring El Morro, one of the oldest fortifications in the Americas, built by the Spanish over a quarter century. Pick up a kite from local vendors and join families picnicking along the fort’s grassy promenade.
Afternoon: Discover Puerto Rican Art
Immerse yourself in the vibrant art scene. Old San Juan and Santurce are home to galleries and museums showcasing local artists and international talent.
East of La Placita lies the prestigious Museo de Arte de Puerto Rico. This cultural institution is set in a historic 17th-century building, offering 24 exhibition galleries and an expansive collection spanning over 400 years.
For a condensed experience, focus on seminal works by Puerto Rican artists like José Campeche and Francisco Oller, along with modern installations by Marta Mabel Pérez. The curated collection of Taíno artifacts provides historic context.
Additionally, check out small galleries featuring contemporary artists gaining international recognition, such as Walter Otrero and Roberto Paradise.
Evening: Experience La Placita
Spend your first night in the Santurce district, known for its bold street art, cocktail bars, and culinary treasures that surround La Placita de Santurce.
Top restaurants and cocktail bars abound here. Asere Kitchen and Bar captures the essence of Old Havana with its vintage decor and delicious passionfruit or habanero mojitos crafted with local rum.
Just south of the plaza, La Penúltima is a beloved community bar known for its colorful murals and chilled Medalla (Puerto Rico’s national beer), making it a great spot to mingle with locals.
After dinner, enjoy numerous bars and live music venues surrounding La Placita, where local folk music and reggaetón set the lively atmosphere.
Day 2
Morning: Enjoy Sun, Sand, and Surf
Select one of San Juan’s stunning beaches for relaxation or adventure. Try snorkeling, jet skiing, paddleboarding, or surfing. The upscale Condado neighborhood attracts visitors seeking luxury and beautiful beach experiences.
For tranquil swimming and snorkeling, visit the sheltered cove at Playita del Condado. Alternatively, enjoy the local vibe at Escambrón Beach, renowned for its postcard-worthy views and decent surf.
For wave riding, novices can head to Pine Grove in Isla Verde, known for gentle waves. Active travelers might rent bikes to explore the coastal scenery along the partially paved boardwalk stretching from Isla Verde to Piñones.
Food kiosks by the beach serve traditional street food, offering must-try items like bacalaítos (codfish fritters) and alcapurrias (fried plantains stuffed with meat).
Afternoon: Shop Local, Shop Cool
Experience Puerto Rico’s vibrant arts scene on Calle Loíza, also known as the “Avenue of the Arts.” This vibrant street is home to art, culture, and unique dining experiences.
Walk along Calle Cerra for iconic murals originating from the annual street art festival Santurce es Ley.
Evening: Sip, Dine, Dance
For a classy cocktail experience, visit the historic Condado Vanderbilt Hotel lobby bar; arrive early for happy hour. Enjoy stunning ocean views while indulging in creative cocktails.
For dining, make reservations at Marmalade, known for gourmet dishes showcasing fresh ingredients. Don’t miss chef Peter Schintler’s signature potato truffle soup.
Afterward, dance the night away at La Factoría, a salsa hotspot with a lively atmosphere, drawing both locals and tourists.
Day 3
Morning: Hike Through the Rainforest
On your final day, venture to El Yunque National Forest, the only rainforest managed by the National Park Service. This ecological wonder offers myriad trails through cloud-laced mountains and vibrant greenery.
The park features several distinct zones and the 5-mile El Yunque trail, which leads to breathtaking summit views. For beginners, the short Big Tree Trail leads to the picturesque La Mina waterfalls.
El Yunque is only 45 minutes from San Juan, and while tours are available, a rental car provides flexibility to explore.
Afternoon: Relax at Luquillo Beach
After your hike, head to Luquillo Beach. This palm-fringed paradise offers calm waters and excellent facilities, making it a perfect relaxation spot.
Local kiosks serve delightful Puerto Rican dishes and fresh seafood. You can enjoy leisure activities like jet skiing and kayaking before or after your meal.
Evening: Celebrate with a Farewell Dinner
Cap off your San Juan adventure at a chic rooftop bar, Arya, offering lagoon views and superb cocktails. Make a reservation for a sunset experience.
For dinner, head to the James Beard-nominated José Enrique. This eatery emphasizes quality ingredients and changes its menu daily based on fresh local produce. Alternatively, savor fine dining at 1919, with its emphasis on fresh seafood and exquisite flavors.
