Windstar Cruises Your Winter, Warmed Up in the Caribbean

Windstar Cruises Your Winter, Warmed Up in the Caribbean. Explore the granite boulders and natural pools of The Baths on Virgin Gorda. Enjoy the boutiques of Gustavia a short tender from St. Barts. Or take in St. Lucia’s majestic Pitons as you sail by on your yacht hosting fewer than 350 guests.

Winter is coming, and your clients are already dreaming of an escape. This is the moment to talk to them about the Caribbean — anchored off pristine Mayreau with the Tobago Cays' reefs a short paddle away, exploring the granite boulders and natural pools of The Baths on Virgin Gorda, browsing the boutiques of Gustavia a short tender from St. Barts, or taking in St. Lucia's majestic Pitons as they sail by on a yacht hosting fewer than 350 guests.


Reserve now and you'll enjoy a complimentary All-Inclusive Package, featuring Wi-Fi, gratuities and select beer, cocktails and wine by the glass (worth more than $1,300 for two on a 7-night sailing) — plus a $300 reduced deposit  


The clients thinking about winter right now are the ones ready to book. Reach out today, and set them up for a warm winter. 



 

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Reroute Your Holidays to the Caribbean

This year, spend the holidays in the Caribbean, anchored off pristine Mayreau, with the reefs of the Tobago Cays a short paddle away. Explore the granite boulders and natural pools of The Baths on Virgin Gorda. Enjoy the boutiques of Gustavia a short tender from St. Barts. Or take in St. Lucia’s majestic Pitons as you sail by on your yacht hosting fewer than 350 guests.

Reserve a warm winter now and enjoy a complimentary All-Inclusive Package, featuring Wi-Fi, gratuities and select beer, cocktails and wine by the glass (worth more than $1,300 for two on a 7-night sailing).
 
 

 

 

 

Christmas at Sea

This Year, Let Someone Else Host the Holidays

 

From crew-led carol sing-alongs to twinkling Christmas lights, here's what the holidays actually feel like at sea — read on for five reasons to make it your tradition too. 

FEATURED VOYAGES

Windward Islands Surf
& Sunsets   

 

November 22, 2026

 

 

from $2,411

 

PER GUEST
 

Island Palm Tree

Classic Caribbean  

 

December 26, 2026

 

from $2,852

PER GUEST
 

Running Holding Hands

San Juan &
the Virgin Islands

 

December 27, 2026

 

from $4,788

PER GUEST
 

San Juan (2)

Beach Fun & Sun: A Remote
Caribbean Getaway 

 

December 19, 2026

 

 

from $3,953

 

PER GUEST
 

Caribbean Blue Waters

Star Collector:
Lovely Leewards

 

December 13, 2026

 

 

from $6,142

 

PER GUEST
 

Piton

Star Collector:
Caribbean Explorations   

 

December 19, 2026

 

from $5,524

PER GUEST
 

Walking Together

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