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
Sort by:  Sailing Date | Price | 
Departure Date:  

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

Starting from $2,699*

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

7 Days - New World Caribbean Trio[San Juan to Colon]

Starting from $3,399*

Cruise Line: Windstar cruises

Ship:  Star Seeker

Sailing Dates: Apr 06 2026

Port: San Juan to Colon

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

Starting from $3,299*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 01 2026

Port: Oranjestad to Colon

10 Days - Gems of the Leeward Islands [San Juan to San Juan]

Starting from $3,599*

Cruise Line: Windstar Cruise

Ship:  Star Pride / Star Seeker

Sailing Dates:  Mar 27 2026 | Oct 28 2026

Port: San Juan to San Juan

10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]

Starting from $4,599*

Cruise Line: Windstar Cruise

Ship:  Wind Spirit

Sailing Dates: Jan 14 2026

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

10 Days - Sublime Southern Caribbean[Bridgetown to Philipsburg, St. Maarten]

Starting from $3,399*

Cruise Line: Windstar cruises

Ship:  Wind Spirit

Sailing Dates: Jan 04 2027

Port: Bridgetown to Philipsburg, St. Maarten

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colon]

Starting from $4,099*

Cruise Line: Windstar Cruise

Ship:  Wind Star | Wind Spirit

Sailing Dates:  Nov 18 2025 | Nov 24 2026

Port: Bridgetown to Colon

11 Days - Stars of the Greater Antilles [Cozumel to St. Maarten]

Starting from $3,999*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 17 2026

Port: Cozumel to St. Maarten

14 days - Star Collector: Lovely Leewards [San Juan to San Juan]

Starting from $3,999*

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 | Nov 08 2026 | Dec 06 2026 | Dec 27 2026 | Jan 03 2027

Port: San Juan to San Juan

14 Days - Star Collector: Leeward & Windward Caribbean Havens [St. Maarten to Bridgetown]

Starting from $4,199*

Cruise Line: Windstar Cruise

Ship:  Wind Surf / Wind Spirit

Sailing Dates:  Jan04 2026 | Feb 21 2026

Port: St. Maarten to Bridgetown

*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.

 
Get Quote Talk To Expert