Caribbean

Caribbean

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you're sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

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.
Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These ..read more
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5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Dec 02 2025

Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten

6 days - San Juan & the Virgin Islands [San Juan to San Juan]

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship:  Star Pride

Sailing Dates:  Nov 3 2024 | Nov 30 2024 | Nov 01 2025 | Nov 15 2025 | Nov 30 2025

Port: San Juan to San Juan

7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship:  Star Legend / Star Pride

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]

Starting from $2,499*

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

7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Starting from $2,399*

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

7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]

Starting from $2,499*

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]

Starting from $2,299*

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]

Starting from $2,399*

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

7 Days - Lush & Lovely Islands of the Lesser Antilles [Philipsburg, St. Maarten to Bridge]

Starting from $2,399*

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

8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]

Starting from $3,199*

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.

 
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