Star Collector: The Best of the Windward & Leeward Isles
 
Philipsburg, St. Maarten to Oranjestad
Sun Jan 4, 2026 - Sun Feb 1, 2026,
 28 days
 on Wind Surf
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Starting from $9,099 USD
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Philipsburg, St. Maarten to Oranjestad
Explore the Caribbean’s most picturesque destinations and little-known treasures while indulging in a longer cruise vacation along the most scenic stops throughout the Windward and Leeward Islands and relaxing afternoon in the warm Caribbean off the Watersports Platform. Swim amid sea turtles, colorful coral, eagle rays, and parrot fish during a snorkel safari off the coast of St. Kitts. Buzz about with a beekeeping guide and sample the delicious sweetness of rare and exotic Black Mangrove honey during an agricultural collective tour outside of Castries. Kayak to a beachside village for beverages and souvenirs during an overnight stay in Jost Van Dyke. Dine on conch fritters paired with tropical refreshments. Walk in the childhood footsteps of the future Empress Josephine among flowers and rustic gardens at the Pagerie Habitation, a former sugar plantation on Martinique. Seek out brown pelicans, blue herons, and iconic pink flamingos while gliding silently along lattice-like mangrove roots in Lac Bay National Park on Bonaire.
voyage map
Popular Highlights
Complimentary laundry
Pack light with complimentary daily laundry service
 
Gustavia Late Night Stays
Late night stays in Gustavia, Pigeon Island, and Les Saintes let you really experience the flavor of these distinct places
Jost Van Dyke
Relish extra beach time with an overnight in Jost Van Dyke
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sun Jan 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 5
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jan 6
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Jan 8
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 9
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 10
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Jan 11
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Jan 12
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Jan 13
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Jan 14
St. John's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 15
Les Saintes
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Jan 16
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 17
Kingstown
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 18
Bridgetown
Arrive:  5:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 19
Anse Mitan
Arrive:  9:00 AM
Depart:  11:00 PM
Watersports Platform: 
Tue Jan 20
Castries
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jan 20
Pigeon Island
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Wed Jan 21
Pigeon Island
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Thu Jan 22
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 23
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Jan 24
St. George's
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 25
Bridgetown
Arrive:  6:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 26
Bequia
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Jan 27
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 28
Soufriere
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Jan 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Jan 30
Kralendijk
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 31
Willemstad
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 1
Oranjestad
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
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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 4 - Sun, Feb 1, 2026
WIND SURF
$11,871
$9,099
THIS
SAILING