
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 - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan 07 2026 | Jan 11 2026 | Feb 28 2026
Port: Philipsburg, St. Maarten to Bridgetown
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
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
10 Days - Gems of the Leeward Islands [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride / Star Seeker
Sailing Dates: Mar 27 2026 | Oct 28 2026
Port: San Juan to San Juan
10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]
Cruise Line: Windstar Cruise
Ship: Wind Spirit
Sailing Dates: Jan 14 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
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
11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colon]
Cruise Line: Windstar Cruise
Ship: Wind Star | Wind Spirit
Sailing Dates: Nov 18 2025 | Nov 24 2026
Port: Bridgetown 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
14 days - Star Collector: Lovely Leewards [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride | Star Seeker
Sailing Dates: Nov 02 2025 | Nov 09 2025 | Nov 16 2025 | Nov 23 2025 | Jan 23 2026 | Jan 30 2026 | Feb 06 2026 | Feb 13 2026 | Feb 20 2026 | Feb 27 2026 | Mar 06 2026 | 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 [St. Maarten to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Jan04 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.