
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.
14 Days - Star Collector: Antilles Adventures [St. Maarten to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan 11 2026 | Feb 28 2026
Port: St. Maarten to Bridgetown
14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Jan 18 2026
Port: Bridgetown to Oranjestad
14 days - Star Collector: Caribbean Explorations [Philipsburg, St. Maarten to Philipsburg]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Dec 07 2025 | Dec 14 2025 | Dec 21 2025 | Jan 31 2026 | Feb 07 2026 | Feb 28 2026 | Mar 14 2026 | Mar 21 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
17 Days - Star Collector: Hidden Gems of the Caribbean [Philip., St. Maarten to Philip.]
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
21 Days - Star Collector: A Lesser Antilles Odyssey [Philip., St. Maarten to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan 04 2026 | Feb 21 2026
Port: Philipsburg, St. Maarten to Bridgetown
*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.