Jewels of the Windward Islands

 
Bridgetown to Bridgetown
Fri Nov 27, 2026 - Fri Dec 4, 2026,
 7 days
 on Star Legend
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Starting from $2,599 USD
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Bridgetown to Bridgetown
This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
voyage map
Popular Highlights
Beach Party
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share.
Fort Hamilton
Walk up Mount Pleasant and see the amazing view from Fort Hamilton on Bequia.
Grenada
Make time for a visit to Grand Etang National Park on Grenada.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Nov 27
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sat Nov 28
Anse Mitan
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Nov 29
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Mon Nov 30
Pigeon Island
Arrive:  
Depart:  6:00 AM
Watersports Platform: 
Mon Nov 30
Castries
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Mon Nov 30
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Tue Dec 1
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 2
St. George's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Dec 3
Bequia
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Dec 4
Bridgetown
Arrive:  5:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
ALL DATES &
FARES
Go All-Inclusive — On Us
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Jan 18 - Sun, Jan 25, 2026
WIND SURF
$3,399
$3,399
Sun, Mar 15 - Sat, Mar 21, 2026
WIND SPIRIT
$3,999
$3,999
Fri, Nov 27 - Fri, Dec 4, 2026
STAR LEGEND
$3,292
$2,599
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SAILING