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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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. |
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 |
Beach Fun & Sun: A Remote Caribbean Getaway
January 2, 2027 | 7 NIGHTSfrom $2,658PER GUEST |
Windward Islands,
November 22, 2026 | 7 NIGHTSfrom $2,691PER GUEST |
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PEACE OF MIND, PROMISEDNOW 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.
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WHERE TO NEXT? |
To reserve your next cruise, contact 905-799-3000 |



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