Windward Island Delights
 
Bridgetown to Bridgetown
Sun Dec 28, 2025 - Sun Jan 4, 2026,
 7 days
 on Wind Spirit
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Starting from $3,199 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
Anse Mitan
Find the botanical gardens, the Old Bread Oven and excellent shopping of Anse Mitan
Dominicas Morne Trois Pitons National Park
Take a hike in Dominica’s Morne Trois Pitons National Park, a UNESCO site and see Trafalgar Waterfalls.
Les Saintes
Even novice snorkelers will delight in exploring the crystal-clear waters of Les Saintes.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sun Dec 28
Bridgetown
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Mon Dec 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Dec 30
Basseterre
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Dec 31
Les Saintes
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 1
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Jan 2
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 3
Anse Mitan
Arrive:  7:30 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 4
Bridgetown
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (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
Holiday Sailings
Pick Your Perk
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, Dec 28 - Sun, Jan 4, 2026
WIND SPIRIT
$3,892
$3,199
THIS
SAILING