El Viejo San Juan, the seven-square-block landmark zone of the island’s capital, is a perfectly microcosm of Spanish Colonial architecture and a walk back through history. In fact, were it not for the chaotic traffic jams that are its liaison with reality, this nearly 500-year-old open-air theatre set would look almost too beautiful to be authentic. Its narrow streets are paved with adoquine (a blue stone used as ballast on Spanish galleons), and its 16t-century fortresses, particularly the impregnable six-level El Morro rising 150 feet above the sea, still strike one as engineering marvels. This showcase of protected old-world landmarks is also chocka-block with fashionable bistros, designer shops, art galleries, churches, and Colonial town houses with flowering wrought-iron balconies.
The elegant El Convento was one of the first historic boutique hotels in the heart of Old San Juan, helping transform the district into one of the most vibrant historic and artistic communities in the Caribbean. The imposing 1651 Carmelite convent (which later served as a dance hall, a Howard Johnson’s, and even a flophouse) has origin details such as wooden beams and handmade tiles. Stop by Cana, its small and popular jazz bar.
High atop the Old City’s North Wall sits the Gallery Inn, six interconnecting town houses that combine to create a quiet, quirky labyrinth of titled staircases, open-air patios, and small pocket gardens. Owner Jan D’Esopo decorated each of the 22 electric rooms, lending an artist’s sensibility while respecting the traditional setting. Its Wine Deck commands the highest point in the city, offering the best views of Old San Juan, the Atlantic Ocean, and San Juan Bay. For those who like Latin music and late nights and don’t mind the noise, Da House (a hotel housed in a former Franciscan monastery) is right above the Nuyorican Cafe, which is the best spot for live salsa and Caribbean-influenced jazz with a mixed-age crowd.