
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.
7 days - Windward Islands Surf & Sunsets - Star Seeker
Cruise Line: Windstar Cruise
Ship: Star Seeker
Sailing Dates: Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026
Port: San Juan to San Juan
7 Days - New World Caribbean Trio - Star Seeker
Cruise Line: Windstar cruises
Ship: Star Seeker
Sailing Dates: Apr 06 2026
Port: San Juan to Colon
8 Days - Star Seeker Christening Sailing - Star Seeker
Cruise Line: Windstar cruises
Ship: Star Seeker
Sailing Dates: Jan 15 2026
Port: Miami to San Juan
8 Days - In the Wake of the Spanish Armadas
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Feb 01 2026
Port: Oranjestad to Colon
10 Days - Gems of the Leeward Islands Star Seeker
Cruise Line: Windstar Cruise
Ship: Star Seeker
Sailing Dates: Mar 27 2026
Port: San Juan to San Juan
11 Days - Colombian & Southern Caribbean Coastlines
Cruise Line: Windstar Cruise
Ship: Wind Star / Wind Spirit
Sailing Dates: Nov 24 2026
Port: Bridgetown to Colon
11 Days - Stars of the Greater Antilles
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Feb 17 2026
Port: Cozumel to St. Maarten
14 days - Star Collector: Lovely Leewards
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 08 2026 | Dec 06 2026 | Dec 27 2026 | Jan 03 2027
Port: San Juan to San Juan
14 Days - Star Collector: Leeward & Windward Caribbean Havens
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan04 2026 | Feb 21 2026
Port: St. Maarten to Bridgetown
14 days - Star Collector: Caribbean Explorations
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 | Dec 19 2026 | Dec 26 2026 | Jan 02 2027 | Jan 09 2027 | Jan 16 2027 | Jan 23 2027 | Jan 30 2027 | Feb 06 2027 | Feb 13 2027 | Feb 20 2027 | Feb 27 2027 | Mar 06 2027 | Mar 13 2027
Port: Philipsburg, St. Maarten 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.
