Jewels of the Windward Islands
 
Bridgetown to Bridgetown
Sat Mar 29, 2025 - Sat Apr 5, 2025,
 7 days
 on Star Pride
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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 29
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Mar 30
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Mon Mar 31
Pigeon Island
Arrive:  
Depart:  5:00 AM
Watersports Platform: 
Mon Mar 31
Castries
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Mon Mar 31
The Pitons
Arrive:  6:30 PM
Depart:  
Watersports Platform: 
Tue Apr 1
Anse Mitan
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 2
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Apr 3
St. George's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Apr 4
Bequia
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Apr 5
Bridgetown
Arrive:  5:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? 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
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
THIS
SAILING
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