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.

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.

Castries is the capital of the island nation of St. Lucia, in the Caribbean Sea. It’s known for palm-lined Vigie Beach and as a port of call for cruise lines, with duty-free shopping near the harbor. The Cathedral Basilica of the Immaculate Conception, with its colorful murals, sits by leafy Derek Walcott Square park. Lively Castries Market is nearby. In the south, Morne Fortune hill offers views of the city.

St. John’s is the capital and key port of the Caribbean island nation of Antigua and Barbuda. The city is home to the Museum of Antigua and Barbuda, with exhibits on indigenous tribes and plantation life. St. John’s Cathedral, a 19th-century Anglican church, is on a hill near the 17th-century Government House. A monument to the nation’s founder, V.C. Bird, is next to the Public Market, which sells crafts and produce.

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.