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Jewels of the Windward Islands
 
Bridgetown to Bridgetown
Sat Mar 21, 2026 - Sat Mar 28, 2026,
 7 days
 on Wind Spirit
?All-inclusive from
$3,222
?Cruise Only From
$2,599
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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
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Day 1: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 3: Little Bay
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
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Day 4: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 5: Roseau
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.
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Day 6: Anse Mitan
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.
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Day 7: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 8: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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.
Grenadines
 Savor the beauty of scenic cruising around St. Vincent & the Grenadines.
St. Lucia
Have extra time at St. Lucia to enjoy more of the beachside resorts and national park there.
St. Lucia Pitons
Stand on deck for scenic cruising past the UNESCO World Heritage Site Pitons (volcanic spires) on St. Lucia.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Mar 21
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Mar 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 23
Little Bay
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 24
Les Saintes
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Mar 25
Roseau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Mar 26
Anse Mitan
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Fri Mar 27
Pigeon Island
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Mar 28
Bridgetown
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Wind Spirit
The Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
Category B
Category B
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $2,599 per guest
? All-inclusive price from $3,222 per guest
Category BX Deluxe
Category BX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $2,799 per guest
? All-inclusive price from $3,422 per guest
Category A
Category A
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $2,999 per guest
? All-inclusive price from $3,622 per guest
Category AX Deluxe
Category AX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $3,199 per guest
? All-inclusive price from $3,822 per guest
Owner's Suite
Owner's Suite
With an expansive 220 square feet, the Owner’s Suite gives you everything offered in a stateroom, plus lots more, including a beautiful sitting area and separate in-room dining space.
? Cruise only from $5,599 per guest
? All-inclusive price from $6,222 per guest
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
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Complimentary All-Inclusive Upgrade
Holiday Sailings
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Dec 7 - Sat, Dec 14, 2024
WIND SPIRIT
$2,799
$2,799
Sat, Dec 21 - Sat, Dec 28, 2024
WIND SPIRIT
$2,899
$2,899
Sat, Jan 4 - Sat, Jan 11, 2025
WIND SPIRIT
$2,999
$2,999
Sat, Jan 18 - Sat, Jan 25, 2025
WIND SPIRIT
$2,999
$2,999
Sat, Feb 1 - Sat, Feb 8, 2025
WIND SPIRIT
$3,199
$3,199
Sat, Feb 15 - Sat, Feb 22, 2025
WIND SPIRIT
$2,999
$2,999
Sat, Mar 29 - Sat, Apr 5, 2025
STAR PRIDE
$2,599
$2,599
Sun, Jan 18 - Sun, Jan 25, 2026
WIND SURF
$3,322
$2,699
Sat, Mar 7 - Sat, Mar 14, 2026
WIND SPIRIT
$3,222
$2,599
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SPIRIT
$3,222
$2,599
THIS
SAILING