Caribe Hilton

With its own beach and large swatches of tropical gardens, the Caribe Hilton is still one of San Juan's finest properties in a city full of them.

The Caribe was constructed in 1949 and played host to numerous celebrities throughout the 1950s and '60s. Its recently renovated rooms are loaded with amenities, and the sprawling pool and beach area includes a lawn chessboard, scores of hammocks and an interesting mini-peninsula with lounge beds.

Sharing a private peninsula with 17 acres of tropical gardens and beach, Caribe Hilton resides between Old San Juan and Condado, home to the city's trendiest clubs and restaurants. Across the open-air lobby from the main entrance is the oceanfront Oasis Bar, where the piña colada was invented in 1954.

Not many hotels can lay claim to their own fort, but Fortín San Gerónimo del Boquerón, which once guarded the entrance to San Juan Bay, is on the grounds of this sprawling resort, one of the largest in Puerto Rico. It has a private beach, a multilevel pool with swim-up bar, a luxurious spa, and one of the best-developed kids' programs on the island.

Covering a 17-acre spread, the location right between Old San Juan and Condado is ideal – a kind of junction between the city's history and its future. Rooms are smallish, standard-issue-corporate in style, but most have balconies and marble bathrooms.