San Juan, Puerto Rico’s capital and largest city, sits on the island’s Atlantic coast. Its widest beach fronts the Isla Verde resort strip, known for its bars, nightclubs and casinos. Cobblestoned Old San Juan features colorful Spanish colonial buildings and 16th-century landmarks including El Morro and La Fortaleza, massive fortresses with sweeping ocean views, as well as the Paseo de la Princesa bayside promenade.

Tortola is the largest of the British Virgin Islands in the Caribbean. It features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove. Road Town, the capital of the British Virgin Islands, has a harbor dotted with sailing boats and is known as a yachting hub. In the island’s southwest, forested Sage Mountain National Park offers trails and sweeping views over neighboring cays.

Bridgetown, the capital of Barbados, is a port city on the island’s southwest coast. It’s known for its British colonial architecture, 17th-century Garrison and horseracing track. Near the central National Heroes Square, which fringes the Constitution River, Nidhe Israel Synagogue and its museum explore the island’s Jewish history. Carlisle Bay is home to 6 shipwreck dive sites, Browne’s Beach and a yacht club.

Basseterre is the capital of the Caribbean island federation of Saint Kitts and Nevis. It’s the gateway to popular Saint Kitts beaches like South Friars Bay. At the city’s heart, Independence Square has an Italian-inspired fountain. Just off the Circus traffic circle, with its Victorian Berkeley Memorial Clock Tower, is the National Museum. In the stately Old Treasury Building, it explores the islands’ colonial past.

St. Croix is one of the U.S. Virgin Islands, in the Caribbean. Bright yellow Fort Christiansvaern is among Christiansted National Historic Site’s Danish colonial buildings. West, St. George Village Botanical Gardens occupies an old sugar plantation. Point Udall’s Millennium Monument marks the easternmost point of U.S. territory. North, Salt River Bay National Park has archaeological sites, mangroves and coral reefs.

San Juan, Puerto Rico’s capital and largest city, sits on the island’s Atlantic coast. Its widest beach fronts the Isla Verde resort strip, known for its bars, nightclubs and casinos. Cobblestoned Old San Juan features colorful Spanish colonial buildings and 16th-century landmarks including El Morro and La Fortaleza, massive fortresses with sweeping ocean views, as well as the Paseo de la Princesa bayside promenade.