With summer coming to a close, clients' minds are already turning to winter — and three regions are ready for them: the Caribbean, Southeast Asia, and the Mediterranean, all sailing on yachts that welcome fewer than 350 guests.  

Think warm-water days off the Marina platform in the Caribbean, a route from Phuket through Singapore to Bangkok's canals in Southeast Asia, or a slower-paced Mediterranean with locals.

DESTINATIONS

YACHTS

SPECIALS

Caribbean voyage is ahead on the calendar with the Marina platform ready to drop, warm water waiting and Gustavia or Jost Van Dyke in the distance. Winter travel can also mean gliding beneath Halong Bay's limestone karsts, or tracing a path from Phuket through Singapore's skyline and on to Bangkok's floating market. Or it can mean a slower Mediterranean, exploring the Riviera and the Dalmatian Coast harbor towns alongside the locals who actually live there.

These winter departures sail on yachts that welcome fewer than 350 guests, and they're already filling in. Wherever you choose, winter is a lot warmer from the deck of a Windstar yacht.

Book and you'll 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.  
 

Where Winter Feels 
Like Summer

Small-ship escapes to plan now, so the cold never has to catch up with you. 

FEATURED VOYAGES

Tantalizing Thailand
& Sparkling Singapore      

January 17, 2027 | 11 NIGHTS

 

from $6,227

PER GUEST
 

Classic Caribbean     

March 6, 2027 | 7 NIGHTS

 

from $3,377

PER GUEST
 

Europe's Winter Riviera  

January 15, 2027 | 7 NIGHTS

 

from $2,847

PER GUEST
 

Vietnam &
Cambodia Revealed    

December 17, 2026  |  10 NIGHTS

 

from $6,513

PER GUEST
 

Winter Italy and 
the Dalmatian Coast 

January 22, 2027 | 8 NIGHTS

 

from $3,259

PER GUEST
 

Beach Fun & Sun:
A Remote Caribbean Getaway  

January 2, 2027 | 7 NIGHTS

 

from $3,568

PER GUEST
 

WHERE TO NEXT?