Jewels of the Windward Islands
 
Bridgetown to Bridgetown
Sat Dec 21, 2024 - Sat Dec 28, 2024,
 7 days
 on Wind Spirit
VIEW ALL DATES
Starting from $3,299 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 2: 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.
VIEW THE JOURNEY
Day 3: 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.
VIEW THE JOURNEY
Day 3: Castries
The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.
VIEW THE JOURNEY
Day 3: The Pitons
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
VIEW THE JOURNEY
Day 4: Kingstown
Charming Kingstown, the capital and main commercial center of St. Vincent & the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765.  Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands.  Other sites to see include St. George’s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary’s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.
VIEW THE JOURNEY
Day 5: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
VIEW THE JOURNEY
Day 6: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
VIEW THE JOURNEY
Day 7: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
VIEW THE JOURNEY
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 Dec 21
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Dec 22
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Mon Dec 23
Pigeon Island
Arrive:  
Depart:  6:00 AM
Watersports Platform: 
Mon Dec 23
Castries
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Mon Dec 23
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Tue Dec 24
Kingstown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Dec 25
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Dec 26
St. George's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 27
Bequia
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Dec 28
Bridgetown
Arrive:  5:00 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.
LEARN MORE →
Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
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 $3,299 per guest
? All-inclusive price from $3,992 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 $3,499 per guest
? All-inclusive price from $4,192 per guest
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.
? Call for Availability
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.
? Call for Availability
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.
? 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
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
Holiday Sailings
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Dec 7 - Sat, Dec 14, 2024
WIND SPIRIT
$3,292
$2,599
Sat, Dec 21 - Sat, Dec 28, 2024
WIND SPIRIT
$3,992
$3,299
THIS
SAILING
Sat, Jan 4 - Sat, Jan 11, 2025
WIND SPIRIT
$3,091
$2,398
Sat, Jan 18 - Sat, Jan 25, 2025
WIND SPIRIT
$4,192
$3,499
Sat, Feb 1 - Sat, Feb 8, 2025
WIND SPIRIT
$4,742
$4,049
Sat, Feb 15 - Sat, Feb 22, 2025
WIND SPIRIT
$4,192
$3,499
Sat, Mar 29 - Sat, Apr 5, 2025
STAR PRIDE
$3,292
$2,599
Sun, Jan 18 - Sun, Jan 25, 2026
WIND SURF
$3,392
$2,699
Sat, Mar 7 - Sat, Mar 14, 2026
WIND SPIRIT
$3,392
$2,699
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SPIRIT
$3,292
$2,599