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.
7 days - Classic Caribbean [St. Maarten to St. Maarten]
![7 days - Classic Caribbean [St. Maarten to St. Maarten]](/images/packages/the-pitons.jpg "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
Port: St. Maarten to St. Maarten
( Note: Optional tours are available from most ports for an additional charge. )
![7 days - Classic Caribbean [St. Maarten to St. Maarten]](/images/packages/extraimages/3171_7Days-Classic-Caribbean-16032024.jpg "7 days - Classic Caribbean [St. Maarten to St. Maarten]")
7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]
![7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]](/images/packages/FalmouthHarbour-PORTS.jpg "7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]")
Cruise Line: Windstar Cruise
Ship: Star Pride / Wind Surf
Sailing Dates: Nov 04 2023 | 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
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]](/images/packages/extraimages/3599_7Days-Beach-Fun-Sun-23032024.jpg "7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]")
14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]
![14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]](/images/packages/Castries-St1-Lucia.jpg "14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]")
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 18 2023
Port: Bridgetown to Oranjestad
( Note: Optional tours are available from most ports for an additional charge. )
![14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]](/images/packages/extraimages/2135_14Days-Star-Collector-Captivating-Caribbean22012022.jpg "14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]")
14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]
![14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]](/images/packages/jost-van-dyke-british-virgin-islands.jpg "14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]")
Cruise Line: Windstar Cruise
Ship: Wind Surf
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
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]](/images/packages/extraimages/253_14Days-Star-Collector-Caribbean-Explorations19032022.jpg "14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]")
11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]
![11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]](/images/packages/Cartagena-caribbean.jpg "11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]")
Cruise Line: Windstar Cruise
Ship: Wind Star
Sailing Dates: Dec 19 2023 | Nov 19 2024
Port: Bridgetown to Colón
( Note: Optional tours are available from most ports for an additional charge. )
![11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]](/images/packages/extraimages/3932_11Days-Colombian-Southern-Caribbean150325.jpg "11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]")
6 Days - San Juan & the Virgin Islands [San Juan to San Juan]
![6 Days - San Juan & the Virgin Islands [San Juan to San Juan]](/images/packages/Philipsburg1-St-Maarten.jpg "6 Days - San Juan & the Virgin Islands [San Juan to San Juan]")
Cruise Line: Windstar Cruise
Ship: Star Pride
Sailing Dates: Nov 03 2024
Port: San Juan to San Juan
( Note: Optional tours are available from most ports for an additional charge. )
![6 Days - San Juan & the Virgin Islands [San Juan to San Juan]](/images/packages/extraimages/3663_6Days-San-Juan-the-Virgin-Islands13122020.jpg "6 Days - San Juan & the Virgin Islands [San Juan to San Juan]")
*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.
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