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Windstar Cruises: Small Ship & Yacht-Style Sailing Cruises

See a world few others will see with Windstar Cruises' fleet of small ships and sailing yachts. With fewer than 350 guests, they visit smaller ports and offer a unique, private yacht-style atmosphere.

To learn more about this cruise line please contact one of our cruise experts.

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Recommended Windstar Cruises

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Windstar Alaska Cruises

7 to 25 Night Alaska Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Star Seeker
Departure:	04/20/2026 to 08/14/2027
Length:	7 to 25 Nights

Starting from

$4,226

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Canada & New England Cruises

11 to 25 Day Canada & New England Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Star Pride
Departure:	8/31/2026 to 10/9/2026
Length:	11 to 25 Days

Starting from

$9,769

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Small-Ship Alaska Cruises on Star Seeker

7 to 25-Day Alaska Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Star Seeker
Departure:	5/7/2026 to 8/21/2027
Length:	7 to 25 Days

Starting from

$5,032

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7-Day Costa Rica & Panama Canal Cruises

Luxury Yacht Cruising, Shipboard Credit and More

Cruise Line:	Windstar Cruises
Ship(s):	Multiple
Departure:	2/23/2026 to 2/2/2027
Length:	7 Days

Starting from

$2,589

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7-Day Tahiti Cruises

Shipboard Credit and Watersports

Cruise Line:	Windstar Cruises
Ship(s):	Star Breeze
Departure:	3/12/2026 to 11/4/2027
Length:	7 Days
Starts:	Papeete, Tahiti

Starting from

$2,999

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Yacht-Style Star Collector Voyages

Back-to-Back Voyages with Free Laundry Service

Cruise Line:	Windstar Cruises
Ship(s):	Multiple
Departure:	5/2/2026 to 1/21/2027
Length:	14 to 25 Days

Starting from

$4,993

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Italy Yacht Cruises

7 to 16-Day Italy Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Multiple
Departure:	5/4/2026 to 10/9/2027
Length:	8 to 16 Days

Starting from

$3,399

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Greece Yacht Cruises

7 to 16-Day Greece Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Multiple
Departure:	3/31/2026 to 10/14/2027
Length:	7 to 16 Days

Starting from

$3,635

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Iceland Yacht Cruises

7 to 21-Day Iceland Cruises

Cruise Line:	Windstar Cruises
Ship(s):	Star Pride
Departure:	6/25/2026 to 08/24/2026
Length:	7 to 21 Days

Starting from

$4,613

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Windstar Cruises offers an intimate, yacht-style cruising experience focused on authentic destinations and personalized service. With a fleet of elegant sailing yachts and all-suite motor yachts, Windstar accesses small ports and hidden harbors that larger ships cannot reach. Guests enjoy open-seating dining inspired by regional cuisine, relaxed onboard ambiance, and immersive shore experiences that highlight local culture. Known for its casual elegance and exceptional crew-to-guest ratio, Windstar appeals to travelers seeking a refined yet unpretentious cruise experience. Sailing to destinations worldwide, Windstar delivers a distinctive blend of adventure, comfort, and understated luxury.

Category

Premium

Popular Destinations

Canada & New England, Caribbean, Costa Rica & Panama Canal, Mediterranean, Northern Europe, South America, South Pacific, U.S. Coastals

Types of Cruisers

Couples, anniversaries, celebratory groups, foodies

To learn more about this cruise line please contact one of our cruise experts.

CONTACT AN AGENT

Ship Images Back to Top

Wind Surf

Wind Star

Wind Spirit

Star Pride

Star Breeze

Star Legend

Star Explorer

Star Seeker

Cruise Line Back to Top

Experts Back to Top

Carol Terhune

Cruise Consultant

CONTACT CAROL

ABOUT CAROL

During Carol’s decades in the travel business, she has traveled to Alaska, the Caribbean, Europe, Hawaii, China and her favorite destination of all, Tahiti. ...Read more

Teresa Skeim

Cruise Consultant

CONTACT TERESA

ABOUT TERESA

Teresa’s mission statement is “Move life forward – live life now, don’t wait!” With that guiding principle in mind, she works tirelessly to help clients ...Read more

Gillian Clark, CTC

Cruise Consultant

CONTACT GILLIAN

ABOUT GILLIAN

Gillian’s passion for travel has brought her to all seven continents, and she uses those vast and varied travel experiences to ensure her discerning clients ...Read more

Expert Reviews & Recommendations Back to Top

Understanding Solo Cruise Fares

By: Maggie Blehert | September 20, 2022

10 Tips for Solo Cruisers: How Cruises are Priced and How We Can Help You One of the most frequent questions we receive at Cruise Specialists is if we offer pricing for solo cruisers. The answer is – most certainly – YES, but there are some things to consider. And it may require flexibility on […] Read more

Cruise Review: The Transformed Windstar Star Breeze

By: Maggie Blehert | October 4, 2021

Fresh off a complete renovation as part of Windstar Cruises’ $250 Million Star Plus Initiative, Cruise Specialists was on board Star Breeze for one of her first voyages back at sea in July 2021. All guests and crew were fully vaccinated. Annie Scrivanich, Senior Vice President of Cruise Specialists, cruised roundtrip St. Maarten to inspect […] Read more

Caribbean Ports: More than Meets the Eye

By: Maggie Blehert | July 21, 2021

If you’ve seen one, you’ve seen them all, right? Cruisers who have been to the islands, will quickly tell you this is a long standing myth! Each island has a different flare, it’s own personality due to cuisine, traditions and yes, even landscape! Of course nearly every Caribbean cruise will offer a break from the rush of […] Read more