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Nestled along the shimmering shores of the Caribbean, Old San Juan captivates visitors with its rich history, colorful architecture, and lively spirit. As you wander the blue cobblestone streets, you’ll be transported to a time when Spanish conquistadors roamed and pirates lurked offshore. This iconic neighborhood is the oldest European-established settlement in the United States, brimming with adventure around every corner.
No visit to Old San Juan is complete without exploring the imposing fortresses that once guarded this strategic port. The formidable Castillo San Felipe del Morro looms over the entrance to the bay, its thick stone walls and sentry boxes evoking tales of battle and bravery. Stroll along the grassy fields as you gaze out over the crashing waves below. At Castillo San Cristóbal, you can wander through a veritable labyrinth of tunnels, ramps, and outcroppings that offered a stalwart defense. Both forts are now overseen by the National Park Service, offering a captivating glimpse into Puerto Rico’s storied past.
As you explore, be sure to follow the enchanting Paseo del Morro, a path hugging the northern coastline. Here, you’ll discover a colony of friendly feral cats (left) cared for by the nonprofit Save a Gato. These whiskered locals lounge in the tropical sun, adding an extra dose of charm to your stroll. At Christmas, the nearby Paseo de la Princesa dazzles with a festive light display, transforming the historic avenue into a twinkling wonderland.
One of the greatest joys of Old San Juan is simply wandering its energetic streets and absorbing the vibrant culture. Colorful colonial buildings adorned with wrought-iron balconies line the narrow lanes, housing chic boutiques, art galleries, and lively restaurants. Calle Fortaleza is a frequent selfie-stop with colorful umbrellas throughout the year and a light display at Christmas (right). Stop for a refreshing piragua (Puerto Rican shaved ice) from a street vendor or indulge in a fruity popsicle from Señor Paleta. As evening falls, the city takes on a magical air as locals and visitors alike gather for drinks, dancing, and lively conversation.
Old San Juan’s diverse culinary scene will delight any foodie. Savor classic Puerto Rican dishes like mofongo (mashed plantains) and lechón asado (spit-roasted pork) or venture beyond to experience the city’s international flavors. Sip velvety hot chocolate concoctions at Chocobar Cortes, a charming cafe devoted to the cacao bean. For an authentic Old San Juan breakfast, join the locals at Cafeteria Mallorca for a delectable mallorca sandwich – a sweet, buttery bread stuffed with savory fillings.
While captivating, Old San Juan can pose some challenges for visitors. The narrow streets were built centuries before cars, so driving is not recommended. Instead, park your rental car and explore on foot or use rideshares to easily navigate the area. Hotel El Colonial is our favorite place to stay in the historic city but the most iconic hotel in the city is probably Hotel El Convento, located in the old convent and across the street from the Cathedral. Visitors need to be prepared for occasional power outages, a lingering effect from Hurricane Maria. To avoid crowds, plan your visit during slower cruise ship seasons or maximize your mornings and evenings when the streets are less congested.
Whether you’re seeking history, cuisine, culture or simply soaking up the laidback island vibe, Old San Juan promises an extraordinary experience. As a U.S. territory, Puerto Rico offers hassle-free travel for Americans while delivering the exotic allure of the Caribbean. So pack your sense of adventure and get ready to be swept away by the charms of this ancient, sun-drenched city where past and present intertwine in unforgettable ways.
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