San Juan shimmers both day and night. Whether it’s the sparkling waters surrounding Castillo San Felipe del Morro, the golden sands of Condado Beach catching the afternoon sun or the stars twinkling above the blue cobblestone streets as the Caribbean sun sets on the horizon, the city is a true feast for the senses. San Juan offers U.S. citizens the chance to experience rich history, stunning scenery and vibrant Puerto Rican culture — all without needing a passport.
The downtown core of San Juan is a bit hilly, but it remains an extremely walkable adventure. Sturdy walking shoes are recommended to help navigate the iconic blue cobblestone streets while exploring the city’s historic sights. Start your walking tour at Fuente Raíces, or the Roots Fountain, which was erected in 1992 to commemorate the 500th anniversary of Columbus’s arrival in Puerto Rico.
From there, a short stroll along the fortified walls of Old San Juan brings you to the iconic San Juan Gate — a grand, red entryway once reserved for royalty and dignitaries during colonial times. Over sixteen feet tall and twenty feet thick, the gate provides an impressive entrance into the heart of the city and the day's exploration.
Continue uphill to Castillo San Felipe del Morro, affectionately known as “El Morro.” As a U.S. National Park site, entry requires either an admission fee or a National Park pass. It’s easy to spend hours exploring its multiple levels, outcroppings and commanding views — picture-perfect backdrops for photos, all while learning how the fort defended San Juan from attacks for centuries.
When finished at El Morro, head downhill along the charming blue-hued streets to the Cathedral of San Juan Bautista, the second-oldest cathedral in the Americas. Originally built in 1521 and rebuilt in the 1540s after a hurricane, the current structure features a beautiful Gothic façade. Inside lies the tomb of Ponce de León, the famed explorer and first Governor of Puerto Rico. His remains were moved here from Cuba in 1912 — though the tomb is easy to miss unless you know to look for it.
Just across the street sits Hotel El Convento, a former convent turned luxury hotel. Rich wood beams, handcrafted tiles and luxe décor offer the perfect backdrop for a world-famous piña colada or a leisurely lunch in the hotel’s tranquil courtyard, which is an ideal spot for a break while sitting surrounded by history.
Fully refreshed, continue your walking tour deeper into historic Old San Juan. Take time to meander through the many colorful boutiques and locally owned shops. Eventually, make your way to Plaza de Armas, a historic main square that’s ideal for an afternoon coffee while enjoying the rhythm of local artists — and the ever-present flocks of city pigeons.
Beyond the historic walled city, the beaches of San Juan await, each with its own distinct vibe. Condado Beach, made famous by movie stars in the 1920s with the opening of the Condado Vanderbilt Hotel, offers a touch of glamour. Meanwhile, Ocean Park Beach, Isla Verde and Escambrón Beach are more popular for snorkeling, surfing or active beach fun. It’s easy to spend days beach-hopping until you find your perfect corner of paradise.
And don’t miss a trip to Casa Bacardí San Juan, the world’s largest rum distillery — just a short ferry or taxi ride from the city center. Several tour options are available, including tastings that teach you how to savor rum like a pro or mixology classes that reveal how to craft world-famous cocktails using Bacardí rum.
Whatever you choose — whether you’re visiting San Juan for a single day on a cruise or settling in for a longer beach escape — you’re bound to fall in love with this vibrant Caribbean gem.
Cole Sjoholm
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