Windstar Cruises Caribbean & Canary Islands sailings

Windstar Cruises Caribbean & Canary Islands sailings. In the Caribbean, that means a quiet harbor on Jost Van Dyke too small for the big ships, a glass of rum poured a few steps from where it's distilled in Antigua's English Harbour, an afternoon in Gustavia before the sun drops over St. Barts. Or, on the other side of the Atlantic, the same rhythm plays out in the Canary Islands, just 60 miles from Morocco at the southernmost edge of Europe.

Caribbean and Canary Islands & Madeira itineraries are open for booking this winter, with multiple departures in each region.
 

Give you the easy win you already trust — quiet Caribbean harbors, beach days and real rum tastings — or something entirely new: volcano hikes, lava tube caves and some of the most reliable whale watching in the world, in the Canary Islands.
 

Book to receive a Complimentary All-Inclusive Package, featuring gratuities, unlimited Wi-Fi, and select beer, cocktails and wine by the glass — plus reduced deposits on voyages through 2027.

 

 

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Rum Here. Volcanoes There

This winter, the real question isn't whether to go somewhere warm — it's which islands you want to wake up in, aboard a yacht that hosts fewer than 350 guests.

In the Caribbean, that means a quiet harbor on Jost Van Dyke too small for the big ships, a glass of rum poured a few steps from where it's distilled in Antigua's English Harbour, an afternoon in Gustavia before the sun drops over St. Barts.

Or, on the other side of the Atlantic, the same rhythm plays out in the Canary Islands, just 60 miles from Morocco at the southernmost edge of Europe. A camel ride across Lanzarote's petrified lava fields in Timanfaya, a hike through La Gomera's laurel cloud forest beneath the volcanic spire of Roque de Agando, an evening tasting Madeira wine at a hillside lodge above Funchal.

Beach days, water so clear you can count the fish beneath you, an afternoon paddleboarding straight off the yacht's own Marina — that's the Caribbean version of this winter. Ducking into a lava tube carved through solid rock, an afternoon watching for whales off Tenerife, nights spent on deck under some of the clearest skies in Europe — that's the Canary Islands version.

Book either destination and your voyage comes with a complimentary All-Inclusive Package — gratuities, unlimited Wi-Fi, and select beer, cocktails and wine by the glass — plus reduced deposits on voyages through 2027.

Both destinations are yours to discover this winter. The only real mistake is picturing yourself on one of these islands — and not being there.  
 

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Palm Trees or Volcanoes?

    

One means swimming off the yacht in calm, warm water. The other means volcanic peaks and near-perfect year-round weather.   

FEATURED VOYAGES

Colorful Canary Islands      

 

January 26, 2027 | 10 NIGHTS

 

 

from $3,170

 

PER GUEST
 

Colorful Canary Islands

Masterpieces at Sea: Gems of the Leeward Islands     

 

October 28, 2026 | 11 NIGHTS

 

from $5,008

PER GUEST
 

St. Lucia

Beach Fun & Sun: A Remote Caribbean Getaway  

 

January 2, 2027 | 7 NIGHTS

 

from $2,658

PER GUEST
 

Caribbean

Hidden Gems of the Canary Islands & Madeira    

 

December 17, 2026  |  10 NIGHTS

 

from $3,670

PER GUEST
 

Canary Islands

Windward Islands, 
Surf & Sunsets 

 

November 22, 2026 | 7 NIGHTS

 

from $2,691

PER GUEST
 

Windward Islands

Star Collector:
Lovely Leewards   

 

December 27, 2026  |  14 NIGHTS

 

from $9,824

PER GUEST
 

Running on the beach
PEACE-OF-MIND

PEACE OF MIND, PROMISED

NOW COMPLIMENTARY

 

If your plans change, your reservation is protected, so you can join us again when you're ready. See terms and conditions.

 

For added coverage throughout your journey, optional Travel Protection is available.

 

WHERE TO NEXT?

To reserve your next cruise, contact 905-799-3000

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Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.

 

Contact our travel experts for more details