- San Juan, Puerto Rico – Historic Old San Juan and stunning beaches.
- Charlotte Amalie, U.S. Virgin Islands (St. Thomas) – Known for duty-free shopping and beaches like Magens Bay.
- Philipsburg, St. Maarten – Offers Dutch and French cultural experiences, and great beaches.
- Bridgetown, Barbados – Famous for beaches, Harrison’s Cave, and colonial history.
- Castries, St. Lucia – Known for the Pitons, volcanic beaches, and rainforests.
- Basseterre, St. Kitts and Nevis – Offers rich history and Brimstone Hill Fortress.
- Oranjestad, Aruba – Known for its Dutch architecture, beaches, and desert landscape.
- Willemstad, Curaçao – Known for colorful buildings, floating markets, and coral reefs.
- George Town, Grand Cayman – Offers Stingray City and Seven Mile Beach.
- Falmouth, Jamaica – Historic town with access to Montego Bay and Ocho Rios.