
Caribbean
While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today are drawn not only by the island's mild climate and beautiful beaches but also its cultural riches. Havana has a wealth of colonial buildings and vintage automobiles, as well as intimate paladares that serve local dishes and street parties that move to the rhythms of mambo and salsa. On the country's southern coast, Cienfuegos has elegant mansions and a 19th-century street plan that earned it a place on UNESCO's list of World Heritage sites.
8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Feb 01 2026
Port: Oranjestad to Colon
11 Days - Stars of the Greater Antilles [Cozumel to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Feb 17 2026
Port: Cozumel to St. Maarten
6 Days - Panama's Pristine Caribbean[Colon to Oranjestad]
Cruise Line: Windstar cruises
Ship: Star Pride
Sailing Dates: Mar 09 2026
Port: Colon to Oranjestad
7 Days - New World Caribbean Trio[San Juan to Colon]
Cruise Line: Windstar cruises
Ship: Star Seeker
Sailing Dates: Apr 06 2026
Port: San Juan to Colon
10 Days - Sublime Southern Caribbean[Bridgetown to Philipsburg, St. Maarten]
Cruise Line: Windstar cruises
Ship: Wind Spirit
Sailing Dates: Jan 04 2027
Port: Bridgetown to Philipsburg, St. Maarten
*Prices are per person, based on double occupancy. Prices do not include Government Fees & Taxes. Pricing and availability subject to change without notice. STIC Travel Group reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.