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.

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.

La Romana is a city on the Dominican Republic’s Caribbean coast and a gateway to nearby resort areas. Overlooking the Chavón River, Altos de Chavón is a re-created 16th-century Mediterranean village with artists' workshops. An obelisk painted with colorful images of local life stands in the city center. South of the city is Catalina Island, with beaches, coral reefs and the wrecked ship of pirate William Kidd.

Saint Martin is part of the Leeward Islands in the Caribbean Sea. It comprises 2 separate countries, divided between its northern French side, called Saint-Martin, and its southern Dutch side, Sint Maarten. The island is home to busy resort beaches and secluded coves. It's also known for fusion cuisine, vibrant nightlife and duty-free shops selling jewelry and liquor.

Antigua is one of the 2 major islands that make up the Caribbean nation of Antigua and Barbuda. Ringed with coral reefs, the island is known for its many sandy beaches. Set along English Harbour, restored Nelson’s Dockyard, which Admiral Horatio Nelson made his base in the 1780s, includes a marina and the Dockyard Museum. Trails lead up to Shirley Heights, a former military lookout with panoramic views. 

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.

Fort-de-France is the capital of the Caribbean island of Martinique, a French overseas territory. It’s known for colonial architecture, ornate iron balconies, tropical flowers and beaches. La Savane park has a statue of Napoleon I’s wife Joséphine, a native of the island. Exhibits at the Martinique Museum of Archaeology and Prehistory focus on the island’s history, especially the pre-Columbian period.

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.