Explore Windstar Voyages to the Caribbean

Windstar knows the way to the Caribbean, offering the ultimate island escape. Picture discovering hidden harbors and charming towns only reachable by small ships.
Details & Inclusions
Let Your Soul Dance Shh, there are still secret places that big ships pass by!
Discover hidden gems untouched by big ships, where time slows down and the day unfolds at your own pace. Your Windstar yacht takes you to secret spots, with serene beaches, quiet bars, and stunning sunsets—perfectly timed for a relaxed, unforgettable experience.
Windstar knows the way to the Caribbean, offering the perfect island getaway. Imagine exploring hidden harbors and tiny towns only accessible to small ships like ours, with time to drop the Watersports Platform in crystal-clear bays and raise the sails to your next destination. On board, enjoy a delicious Signature Onboard Barbecue by the pool and an unforgettable day on a secluded beach for Windstar’s Signature Beach Party, complete with an elaborate buffet and watersports. Your dream Caribbean escape awaits!
Choose your favorite sailing below or contact our Bon Voyage specialists at 1-800-439-7963 and ask our experts how to get extra perks on the new itineraries like shipboard credit & more!
Itineraries
- 7-night Bermuda Bliss CruiseNew York City -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Oct 19, 2025Prices From
$2,426 - 24-night Star Collector: Classic Crossing To Spain & More CruiseBarcelona -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Oct 25, 2025Prices From
$6,890 - 7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Oct 26, 2025Prices From
$2,662 - Extra Amenities Included7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 2, 2025Prices From
$2,862 - Extra Amenities Included14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 2, 2025Prices From
$4,693 - Extra Amenities Included14-night Ocean CrossingsLisbon -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Nov 4, 2025Prices From
$2,625 - 7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 9, 2025Prices From
$2,630 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 9, 2025Prices From
$4,193 - 7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 16, 2025Prices From
$2,662 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 16, 2025Prices From
$4,193 - 11-night Columbian & Southern Caribbean CoastlinesBridgetown (Barbados) -> Colon (Panama)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Nov 18, 2025Prices From
$4,241 - 18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama CanalBridgetown (Barbados) -> Puerto Caldera (Puntarenas)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Nov 18, 2025Prices From
$7,911 - Extra Amenities Included19-night Star Collector: Hearty Ports & Rum Punches - A Trans-Atlantic CrossingLisbon -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Nov 18, 2025Prices From
$3,680 - Extra Amenities Included7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 23, 2025Prices From
$2,630 - Extra Amenities Included14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 23, 2025Prices From
$4,193 - Extra Amenities Included7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Nov 30, 2025Prices From
$2,662 - 12-night Star Collector: Ivory Beaches & Sapphire Seas of the CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 2, 2025Prices From
$3,502 - 5-night Barefoot Break in the British Virgin IslandsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 2, 2025Prices From
$2,150 - 7-night Classic CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 7, 2025Prices From
$2,351 - Extra Amenities Included14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 7, 2025Prices From
$3,819 - Extra Amenities Included6-night The Spanish Main: Rise Of The New World CruiseSan Juan -> Colon (Panama)
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Dec 7, 2025Prices From
$2,535 - Extra Amenities Included7-night Enchanting Colombia And Panamanian Islands CruiseColon (Panama) -> Oranjestad, Aruba
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Dec 13, 2025Prices From
$2,615 - Extra Amenities Included7-night Beach Fun & Sun: A Remote Caribbean GetawaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 14, 2025 - Extra Amenities Included14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 14, 2025Prices From
$4,619 - 8-night An ABC Christmas CruiseOranjestad, Aruba -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Dec 20, 2025Prices From
$2,926 - 7-night Classic CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 21, 2025Prices From
$2,951 - 14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 21, 2025Prices From
$5,019 - Extra Amenities Included7-night Beach Fun & Sun: A Remote Caribbean GetawaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Dec 28, 2025 - Extra Amenities Included7-night Windward Island Delights CruiseBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Dec 28, 2025Prices From
$3,116 - 7-night Beach Fun & Sun: A Remote Caribbean GetawaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 4, 2026 - 14-night Star Collector: Leeward & Windward Caribbean HavensSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 4, 2026Prices From
$4,147 - 21-night Star Collector: A Lesser Antilles OdysseySt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 4, 2026Prices From
$6,370 - 55-night Star Collector: A Grand Caribbean AdventureSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 4, 2026Prices From
$19,546 - 28-night Star Collector: The Best Of The Windward & Leeward Isles CruiseSt. Maarten (Philipsburg) -> Oranjestad, Aruba
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 4, 2026Prices From
$9,195 - 14-night Star Collector: Antilles AdventuresSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 11, 2026Prices From
$4,259 - 7-night Lush & Lovely Island of the Lesser AntillesSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 11, 2026Prices From
$2,636 - 17-night Star Collector: Hidden Gems of the CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Jan 14, 2026Prices From
$5,594 - 10-night Blue Waters Of The Leeward Islands CruiseSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Jan 14, 2026Prices From
$4,233 - 8-night Star Seeker Christening: Dominican Republic and BVI Adventure CruiseMiami -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Jan 15, 2026Prices From
$5,896 - Extra Amenities Included7-night Jewels of the Windward IslandsBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 18, 2026Prices From
$2,722 - Extra Amenities Included14-night Star Collector: Captivating CaribbeanBridgetown (Barbados) -> Oranjestad, Aruba
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 18, 2026Prices From
$4,947 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> Mayreau, Grenadines
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Jan 23, 2026 - 7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Jan 23, 2026Prices From
$3,762 - 7-night Beach Fun & Sun: A Remote Caribbean GetwaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Jan 24, 2026Prices From
$2,760 - Extra Amenities Included15-night Star Collector: Windward Islands & Spanish New WorldBridgetown (Barbados) -> Colon (Panama)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 25, 2026Prices From
$5,366 - Extra Amenities Included7-night Windward Ways & Tobago Cays CruiseBridgetown (Barbados) -> Oranjestad, Aruba
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Jan 25, 2026Prices From
$3,024 - 7-night Windward Islands Surf & Sunsets CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Jan 30, 2026Prices From
$3,427 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Jan 30, 2026Prices From
$7,590 - Extra Amenities Included7-night Beach Fun & Sun: A Remote Caribbean GetwaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Jan 31, 2026 - 14-night Star Collector: Caribbean ExplorationSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Jan 31, 2026Prices From
$4,478 - Extra Amenities Included8-night In the Wake of the Spanish ArmadasOranjestad, Aruba -> Colon (Panama)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 1, 2026Prices From
$3,341 - 16-night Star Collector: Natural History Meets Ancient Mystery: Latin America & BeyondOranjestad, Aruba -> Cozumel
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 1, 2026Prices From
$5,286 - Extra Amenities Included7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 6, 2026Prices From
$4,062 - Extra Amenities Included14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 6, 2026Prices From
$6,790 - Extra Amenities Included7-night Classic CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 7, 2026Prices From
$2,717 - Extra Amenities Included14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 7, 2026Prices From
$4,878 - 8-night Mayan LegaciesColon (Panama) -> Cozumel
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 9, 2026Prices From
$3,344 - 19-night Star Collector: Caribbean Cultures: Latin America & the Greater AntillesColon (Panama) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 9, 2026Prices From
$6,208 - 7-night Windward Islands Surf & Sunsets CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 13, 2026Prices From
$3,427 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 13, 2026Prices From
$5,890 - Extra Amenities Included7-night Beach Fun & Sun: A Remote Caribbean GetwaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 14, 2026 - 11-night Stars of the Greater AntillesCozumel -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 17, 2026Prices From
$4,063 - 18-night Star Collector: Deep Dive Into the Blue: Underwater Worlds of the CaribbeanCozumel -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 17, 2026Prices From
$5,715 - Extra Amenities Included7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 20, 2026Prices From
$3,362 - Extra Amenities Included14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 20, 2026Prices From
$5,799 - 14-night Star Collector: Leeward & Windward Caribbean HavensSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 21, 2026Prices From
$4,181 - 7-night Windward Islands Surf & Sunsets CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 27, 2026Prices From
$3,436 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Feb 27, 2026Prices From
$14,799 - Extra Amenities Included7-night Lush & Lovely Islands of the Lesser AntillesSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 28, 2026Prices From
$2,520 - Extra Amenities Included14-night Star Collector: Antilles AdventureSt. Maarten (Philipsburg) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Feb 28, 2026 - 7-night Classic CaribbeanSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 28, 2026Prices From
$2,651 - 14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Feb 28, 2026Prices From
$4,619 - 7-night San Juan & The Virgin Islands CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Mar 6, 2026Prices From
$7,562 - 14-night Star Collector: Lovely Leewards CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Mar 6, 2026Prices From
$13,696 - 7-night Jewels of the Windward IslandsBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Mar 7, 2026 - 14-night Star Collector: Captivating CaribbeanBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Mar 7, 2026Prices From
$4,133 - Extra Amenities Included7-night Beach Fun & Sun: A Remote Caribbean GetawaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Mar 7, 2026 - Extra Amenities Included7-night Windward Islands Surf & Sunsets CruiseSan Juan -> San Juan
Cruise Line
Windstar CruisesCruise Ship
Star SeekerDeparts
Mar 13, 2026Prices From
$3,033 - Extra Amenities Included7-night Windward Island DelightsBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Mar 14, 2026 - Extra Amenities Included14-night Star Collector: Captivating CaribbeanBridgetown (Barbados) -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Wind SpiritDeparts
Mar 14, 2026 - 14-night Star Collector: Caribbean ExplorationsSt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Mar 14, 2026Prices From
$4,119 - 7-night Beach Fun & Sun: A Remote Caribbean GetawaySt. Maarten (Philipsburg) -> St. Maarten (Philipsburg)
Cruise Line
Windstar CruisesCruise Ship
Wind SurfDeparts
Mar 14, 2026 - Extra Amenities Included7-night Windward Ways and Tobago Cays CruiseOranjestad, Aruba -> Bridgetown (Barbados)
Cruise Line
Windstar CruisesCruise Ship
Star PrideDeparts
Mar 15, 2026Prices From
$2,619
Terms & Conditions
Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections. Other restrictions may apply. Contact Bon Voyage Travel for complete terms and conditions.