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.
6 days - San Juan & the Virgin Islands [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride | Star Seeker
Sailing Dates: Nov 30 2024 | Nov 01 2025 | Nov 15 2025 | Nov 30 2025 | Jan 23 2026 | Feb 06 2026 | Feb 20 2026 | Mar 06 2026
Port: San Juan to San Juan
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
Port: San Juan to San Juan
7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]
Cruise Line: Windstar Cruise
Ship: Star Pride | Wind Surf
Sailing Dates: Dec 14 2024 | Jan 11 2025 | Feb 22 2025
Port: Bridgetown to Oranjestad
7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride | Star Seeker
Sailing Dates: Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026
Port: San Juan to San Juan
7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Star Pride / Wind Spirit
Sailing Dates: Dec 07 2024 | Dec 21 2024 | Jan 04 2025 | Jan 18 2025 | Feb 01 2025 | Feb 15 2025 | Mar 29 2025 | Jan 18 2026 | Mar 07 2026 | Mar 21 2026
Port: Bridgetown to Bridgetown
14 days - Star Collector: Caribbean Explorations [Philipsburg, St. Maarten to Philipsburg]
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: Philipsburg, St. Maarten to Philipsburg, St. Maarten
7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Star Pride / Wind Surf
Sailing Dates: Dec 22 2024 | Dec 14 2024 | Jan 04 2025 | Jan 11 2025 | Feb 22 2025 | Mar 15 2025 | Jan 25 2026
Port: Oranjestad to Bridgetown
7 days - Classic Caribbean [Philipsburg, St. Maarten to Philipsburg, St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Dec 21 2024 | Jan 04 2025 | Jan 18 2025 | Jan 25 2025 | Feb 08 2025 | Feb 22 2025 | Mar 01 2025 | Mar 15 2025 | Dec 21 2025 | Feb 07 2026 | Feb 28 2026 | Mar 21 2026
Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten
7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [Philipsburg, St. Maarten to Philips]
Cruise Line: Windstar Cruise
Ship: Wind Spirit / Wind Surf
Sailing Dates: Dec 28 2024 | Jan 11 2025 | Feb 01 2025 | Feb 15 2025 | Mar 08 2025 | Mar 22 2025 | 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
11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colon]
Cruise Line: Windstar Cruise
Ship: Wind Star | Wind Spirit
Sailing Dates: Mar 15 2025 | Nov 18 2025
Port: Bridgetown 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.