Lush & Lovely Islands of the Lesser Antilles
 
Philipsburg, St. Maarten to Bridgetown
Sat Feb 28, 2026 - Sat Mar 7, 2026,
 7 days
 on Wind Spirit
VIEW ALL DATES
Starting from $2,499 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
Philipsburg, St. Maarten to Bridgetown
Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.
voyage map
Popular Highlights
Philipsburg
Grab your walking shoes and your credit card for the short walk from the Philipsburg pier to over 500 duty-free shops or find a cozy spot at one of the beachfront bars along the boardwalk, relax and take in some people watching.
Dominica
See the unspoiled natural landscape, black-sand beaches and botanical gardens of Dominica.
Gustavia
Shop Gustavia's duty-free boutiques or grab a glass of the island’s signature ti punch at a beachside bar.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Feb 28
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 1
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Mon Mar 2
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Mar 3
St. John's
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Wed Mar 4
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Mar 5
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Mar 6
Mayreau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Mar 7
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 $2,499 per guest
? All-inclusive price from $3,192 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
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
Sun, Jan 11 - Sun, Jan 18, 2026
WIND SURF
$3,292
$2,599
Sat, Feb 28 - Sat, Mar 7, 2026
WIND SPIRIT
$3,192
$2,499
THIS
SAILING