Windward Island Delights
 
Bridgetown to Bridgetown
Sun Dec 28, 2025 - Sun Jan 4, 2026,
 7 days
 on Wind Spirit
?All-inclusive from
$3,522
?Cruise Only From
$2,899
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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: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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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: 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 7: 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 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
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.
Montserrat
Visit the “Pompeii of the Caribbean” on Montserrat, half lush and green, half covered in ash.
St. Lucia
Have extra time at St. Lucia to enjoy more of the beachside resorts and national park there.
St. Lucia Pitons
The UNESCO-site Pitons stand majestically above the beautiful beach of Pigeon Island where you will feast on the Signature Beach Barbecue
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports 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:  6:00 PM
Watersports Platform: 
Fri Jan 2
Pigeon Island
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 3
Anse Mitan
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 4
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 $2,899 per guest
? All-inclusive price from $3,522 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 $3,199 per guest
? All-inclusive price from $3,822 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 $3,399 per guest
? All-inclusive price from $4,022 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 $3,599 per guest
? All-inclusive price from $4,222 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 $5,999 per guest
? All-inclusive price from $6,622 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
Last Minute Cruise Deals
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 14 - Sat, Dec 21, 2024
WIND SPIRIT
$2,746
$2,123
Sat, Dec 28 - Sat, Jan 4, 2025
WIND SPIRIT
Call For Availability
Sat, Jan 11 - Sat, Jan 18, 2025
WIND SPIRIT
$3,399
$3,399
Sat, Jan 25 - Sat, Feb 1, 2025
WIND SPIRIT
$3,429
$3,429
Sat, Feb 8 - Sat, Feb 15, 2025
WIND SPIRIT
$3,399
$3,399
Sat, Mar 22 - Sat, Mar 29, 2025
STAR PRIDE
Call For Availability
Sun, Dec 28 - Sun, Jan 4, 2026
WIND SPIRIT
$3,522
$2,899
THIS
SAILING
Sat, Mar 14 - Sat, Mar 21, 2026
WIND SPIRIT
$3,222
$2,599