
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
Cruise Line: Windstar Cruise
Ship: Star Pride | Star Seeker
Sailing Dates: Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026 | Nov 08 2026 | Nov 22 2026 | Dec 06 2026 | Dec 20 2026 | Jan 03 2027
Port: San Juan to San Juan
7 days - Jewels of the Windward Islands
Cruise Line: Windstar Cruise
Ship: Wind Surf / Star Pride / Wind Spirit
Sailing Dates: Jan 18 2026 | Mar 07 2026 | Mar 21 2026
Port: Bridgetown to Bridgetown
7 days - Classic Caribbean
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Dec 21 2025 | Feb 07 2026 | Feb 28 2026 | Mar 21 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
7 Days - Mind, Body and Spirit Collection: Bermuda Bliss
Cruise Line: Windstar cruises
Ship: Star Pride
Sailing Dates: Oct 19 2025
Port: New York City to San Juan
6 Days - Panama's Pristine Caribbean
Cruise Line: Windstar cruises
Ship: Star Pride
Sailing Dates: Mar 09 2026
Port: Colon to Oranjestad
7 days - San Juan & the Virgin Islands
Cruise Line: Windstar Cruise
Ship: Star Pride | Star Seeker
Sailing Dates: Nov 01 2025 | Nov 15 2025 | Nov 30 2025 | Jan 23 2026 | Feb 06 2026 | Feb 20 2026 | Mar 06 2026 | Nov 15 2026 | Nov 15 2026 | Dec 13 2026 | Dec 27 2026 | Jan 10 2027
Port: San Juan to San Juan
7 Days - Beach Fun & Sun: A Remote Caribbean Getaway
Cruise Line: Windstar Cruise
Ship: Wind Spirit / Wind Surf
Sailing Dates: Dec 14 2025 | Dec 28 2025 | Jan 04 2026 | Jan 24 2026 | Jan 31 2026 | Feb 14 2026 | Feb 21 2026 | Mar 07 2026 | Mar 14 2026 | Mar 28 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
7 Days - Windward Ways & Tobago Cays
Cruise Line: Windstar Cruise
Ship: Star Pride / Wind Surf
Sailing Dates: Jan 25 2026
Port: Oranjestad to Bridgetown
7 Days - Windward Island Delights
Cruise Line: Windstar cruises
Ship: Wind Spirit
Sailing Dates: Dec 28 2025 | Mar 07 2026
Port: Bridgetown to Bridgetown
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
*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.