Jewels of the Windward Islands
 
Bridgetown to Bridgetown
Sun Mar 15, 2026 - Sat Mar 21, 2026,
 6 days
 on Wind Spirit
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Starting from $2,499 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
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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 2: Tobago Cays
Sail, snorkel, or beachcomb in complete seclusion in this unspoiled tropical paradise accessible only by boat. Quiet coves like Horseshoe Reef are home to fantastic coral reefs, while nearby Baradel offers an excellent opportunity to observe the area’s famous sea turtles. Crystalline waters and perfect weather make this an ideal spot to play in the sea
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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.
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Day 4: 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 4: 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.
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Day 4: 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.
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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.
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Day 6: 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.
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Day 7: 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
MarinaWatersports Platform: 
Sun Mar 15
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 16
Tobago Cays
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 17
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Wed Mar 18
Pigeon Island
Arrive:  
Depart:  6:00 AM
Watersports Platform: 
Wed Mar 18
Castries
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Wed Mar 18
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Thu Mar 19
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Mar 20
Bequia
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Mar 21
Bridgetown
Arrive:  5:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
? Call for Availability
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 $2,499 per guest
? All-inclusive price from $2,499 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 $2,699 per guest
? All-inclusive price from $2,699 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 $2,899 per guest
? All-inclusive price from $2,899 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 $3,099 per guest
? All-inclusive price from $3,099 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 $5,499 per guest
? All-inclusive price from $5,499 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
Marina
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
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
$2,999
$2,999
Sun, Mar 15 - Sat, Mar 21, 2026
WIND SPIRIT
$2,499
$2,499
THIS
SAILING