ARRIVAL
STAY
MORNING: SIGHTSEEING
AFTERNOON: BEACHES
EVENING: DINING & NIGHTLIFE
ARRIVAL
Conveniently, this majestic place is part of U. S. territory. That means no passport, no currency switch, and no change in cell service for visitors from the States. It’ s close enough for an easy trip( flight time is just under 4 hours), yet far enough away to feel like a genuine escape. Additionally, travelers don’ t need to go through United States Customs and Border Protection checkpoints. Fly nonstop from Washington into Puerto Rico’ s main airport, Luis Muñoz Marín International Airport( SJU), located close to the heart of San Juan.
STAY
From resorts with luxurious accommodations to charming boutique hotels, there are many options to choose from in San Juan. If you are looking for a place that is both secluded and close to the city’ s center, head to the Caribe Hilton, a paradise-like hotel offering everything you could imagine on its property. With its nine restaurants, pool, bar, spa, and daily resort activities, Caribe Hilton is an inviting oasis. Similarly, La Concha Renaissance, Autograph Collection, is another resort hotel known for its excellent accommodations and on-site activities, including its iconic, highly praised casino. Located in the Condado neighborhood of San Juan, La Concha Renaissance sits on a large stretch of public beach and is just a short walk from many restaurants and bars. Alternatively, head to The Gallery Inn, a National Historic Landmark and boutique hotel set in the famous Old San Juan neighborhood. The property is known for its exceptional offerings and experiences— including its concert venues featuring both worldrenowned and emerging musicians, as well as its rooftop bar and terrace with sweeping views of the Atlantic Ocean.
MORNING: SIGHTSEEING
There are countless historic sights to see in San Juan, especially in Old San Juan— a well-preserved district that feels like a time capsule. Start your morning with a step back in time as you stroll through the area’ s streets, where you’ ll find Spanish colonial architecture and lively promenades en route to the city’ s grand fortifications and centuriesold churches.
Head to one of Puerto Rico’ s most famous landmarks, Castillo San Felipe del Morro, or simply El Morro. Admire the fortress’ s six levels of tunnels, barracks, and storerooms. Situated on the edge of the Atlantic, El Morro was built by Spanish colonizers to defend the island from sea attacks, and it has never been conquered. Likewise, Castillo San Cristóbal is another fortress meant to protect San Juan from land attacks. This site, which took more than 150 years to build, is considered the largest fortress in the Americas, covering over 27 acres. Next, visit Catedral de San Juan, the second-oldest church in the Americas. This architectural gem, inspired by medieval design, displays Spanish colonial influence and is best known for its ornate arches and stained-glass windows.
AFTERNOON: BEACHES
Spend your afternoon swimming, snorkeling, surfing, or relaxing at one of San Juan’ s many beautiful beaches. There are countless shoreline options, all featuring bright turquoise waters with clear visibility thanks to the island’ s reef protection and calm seas.
For a family outing, head to Escambrón, a Blue Flag beach. Protected by coral reefs that make the waters great for snorkeling, Escambrón is an exciting spot for interacting with Puerto Rico’ s vibrant sea life. Just a short walk or bike ride away, La Playita del Condado is also a safe and fun place for swimming and snorkeling. This small but notable beach is set against a backdrop of modern buildings, creating a striking contrast between beach scenery and city life.
If you’ re seeking a bustling scene, visit Condado Beach, an upscale area with palm-lined sands, luxury hotels, and nearby restaurants and bars spread along the beachfront. Likewise, Isla Verde is one of the most popular beaches in the metropolitan area, with spots for both surfing and relaxing. For a quieter( but equally beautiful) afternoon, head to Ocean Park, a local favorite that tends to be less crowded, known for its peaceful atmosphere, and popular with kitesurfers.
EVENING: DINING & NIGHTLIFE
In San Juan, dining isn’ t limited to just the plate— it pulls you into a vibrant, deeply rooted food culture. Take a walk through Old San Juan and stroll along Calle Fortaleza, often called‘ umbrella street,’ because of the colorful umbrellas hanging overhead. You’ ll eventually reach the famous Barrachina. Situated in a two-centuryold colonial building with an interior courtyard, the restaurant has been delighting locals and visitors for over 40 years. In addition to its iconic location and stunning architecture, Barrachina is renowned for serving authentic Puerto Rican cuisine and is believed to be the birthplace of the world-famous piña colada.
Enjoy a walk along San Juan’ s most famous promenade, El Paseo de la Princesa, taking in views of the bay, El Yunque National Rainforest, and the Sierra de Luquillo Mountains on your way to Princesa Gastrobar, one of the city’ s top gems. The restaurant features an open terrace surrounded by trees and native vegetation just off the promenade, and its delicious food matches its breathtaking scenery. With techniques and flavors rooted in century-old traditions and infused with Puerto Rican culture, history, and identity, you can indulge in many favorites like mofongo, arroz con gandules, and more. Since you’ re in the rum capital of the world, be sure to pair your meal with a glass. Princesa Gastrobar proudly offers every kind of rum produced on the island.
To keep the excitement going, you’ ll probably want to head to the Santurce neighborhood for a nightcap at a local bar or to really dive into the island’ s music and dance scene. The area, home to a historic market square, comes alive every evening with activity. It’ s uniquely vibrant with a variety of rhythms and movements— including salsa, plena, bomba, and more— making nightlife in Puerto Rico and its Santurce neighborhood spirited at all hours. Check out La Respuesta, a club and pub where music, dance, and entertainment flourish, or visit La Placita de Santurce, an entire block filled with outdoor festivities.
San Juan’ s beauty lies in how effortlessly it blends relaxation, culture, and adventure into a single day. From historic fortresses to sparkling shores and unforgettable flavors, the city invites you to explore at your own pace. And as the night winds down, you’ re left with the unmistakable sense that this is a place worth returning to— again and again.
GETTING THERE
Frontier Airlines started new service in May, offering nonstop service from Washington Dulles International Airport( IAD) to Puerto Rico’ s Luis Muñoz Marin International Airport( SJU), 3x weekly through winter. United Airlines offers nonstop service from IAD to SJU twice daily. JetBlue provides nonstop service from Ronald Reagan Washington National Airport( DCA) to SJU once daily.
WINTER 2025-26
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