
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 islandâs 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 UNESCOâs list of World Heritage sites.
6 days - San Juan & the Virgin Islands [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 16 2024 | Nov 30 2024 | Nov 01 2025 | Nov 15 2025 | Nov 29 2025
Port: San Juan to San Juan
( Note: Optional tours are available from most ports for an additional charge. )
13 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
( Note: Optional tours are available from most ports for an additional charge. )
7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 09 2024 | Nov 23 2024 | Nov 08 2025 | Nov 22 2025
Port: San Juan to San Juan
( Note: Optional tours are available from most ports for an additional charge. )
7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]
Cruise Line: Windstar Cruise
Ship: Star Legend / Star Pride
Sailing Dates: Jan 20 2024 | Dec 14 2024 | Jan 11 2025 | Feb 22 2025
Port: Bridgetown to Oranjestad
( Note: Optional tours are available from most ports for an additional charge. )
7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Star Pride / Wind Spirit
Sailing Dates: Mar 21 2024 | Mar 28 2024 | 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
( Note: Optional tours are available from most ports for an additional charge. )
11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]
Cruise Line: Windstar Cruise
Ship: Wind Star / Wind Spirit
Sailing Dates: Mar 10 2024 | Mar 16 2024 | Mar 15 2025 | Nov 18 2025 | Dec 27 2025
Port: Bridgetown to Colón
( Note: Optional tours are available from most ports for an additional charge. )
7 days - Classic Caribbean [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Surf
Sailing Dates: Dec 09 2023 | Dec 23 2023 | Jan 06 2024 | Jan 20 2024 | Feb 03 2024 | Feb 17 2024 | Mar 02 2024 | Mar 16 2024 | 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: St. Maarten to St. Maarten
( Note: Optional tours are available from most ports for an additional charge. )
7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Spirit / Wind Surf
Sailing Dates: Dec 16 2023 | Dec 30 2023 | Jan 13 2024 | Jan 27 2024 | Feb 10 2024 | Feb 24 2024 | Mar 09 2024 | Mar 23 2024 | 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: St. Maarten to St. Maarten
( Note: Optional tours are available from most ports for an additional charge. )
14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]
Cruise Line: Windstar Cruise
Ship: Wind Surf / Wind Spirit
Sailing Dates: Dec 09 2023 | Dec 16 2023 | Dec 23 2023 | Dec 30 2023 | Jan 06 2024 | Jan 13 2024 | Jan 20 2024 | Jan 27 2024 | Feb 03 2024 | Feb 10 2024 | Feb 17 2024 | Feb 24 2024 | Mar 02 2024 | Mar 09 2024 | Mar 16 2024 | 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
( Note: Optional tours are available from most ports for an additional charge. )
6 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]
Cruise Line: Windstar Cruise
Ship: Star Pride / Wind Surf
Sailing Dates: Dec 16 2023 | Dec 22 2024 | Jan 13 2024 | Jan 20 2024 | Feb 10 2024 | Mar 09 2024 | Dec 14 2024 | Jan 04 2025 | Jan 11 2025 | Feb 22 2025 | Mar 15 2025 | Jan 25 2025
Port: Oranjestad to Bridgetown
( Note: Optional tours are available from most ports for an additional charge. )
*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.