Jewels of the Windward Islands
 
Bridgetown to Bridgetown
Sat Mar 21, 2026 - Sat Mar 28, 2026,
 7 days
 on Wind Spirit
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Starting from $2,599 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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Mar 21
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Mar 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Mar 23
Basseterre
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Mar 24
Les Saintes
Arrive:  9:00 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:  5:00 PM
Watersports Platform: 
Fri Mar 27
Mayreau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Mar 28
Bridgetown
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
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 $3,292 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
ALL DATES &
FARES
Last Minute Cruise Deals
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
Sat, Mar 29 - Sat, Apr 5, 2025
STAR PRIDE
Call For Availability
Sun, Jan 18 - Sun, Jan 25, 2026
WIND SURF
$3,392
$2,699
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SPIRIT
$3,292
$2,599
THIS
SAILING