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.
10 Days - Hidden Treasures of the Lesser Antilles [ Bridgetown to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Nov 27 2024
Port: Bridgetown to Bridgetown
10 Days - Blue Waters of the Leeward Islands [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: St. Maarten to St. Maarten
11 Days - Colombian & Southern Caribbean Coastlines [Colon to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Star / Wind Spirit
Sailing Dates: Mar 15 2025 | Nov 18 2025 | Dec 27 2025
Port: Colon to Bridgetown
11 Days - Boston Sights, Warm Caribbean Nights [Boston to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Oct 23 2024
Port: Boston to San Juan
14 days - Star Collector: Lovely Leewards [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 03 2024 | Nov 16 2024 | Nov 23 2024 | Nov 01 2025 | Nov 08 2025 | Nov 15 2025 | Nov 22 2025
Port: San Juan to San Juan
14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Dec 21 2024 | Dec 28 2024 | Jan 04 2025 | Jan 11 2025 | Jan 25 2025 | Feb 01 2025 | Feb 08 2025 | Feb 15 2025 | Mar 01 2025 | Mar 08 2025 | Mar 15 2025 | 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: St. Maarten to St. Maarten
17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: St. Maarten to St. Maarten
21 Days - Star Collector: A Lesser Antilles Odyssey [St. Maarten to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf Wind Spirit
Sailing Dates: Jan 04 2026 | Feb 21 2026
Port: 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.