Star Collector: Merry Christmas & Happy New Years from the Caribbean

 
Oranjestad to Bridgetown
Sat Dec 20, 2025 - Sun Jan 4, 2026,
 15 days
 on Wind Spirit
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Oranjestad to Bridgetown
Celebrate the holidays on a Caribbean voyage like no other. Begin in the Dutch Caribbean with Aruba’s pastel charm, Curaçao’s colorful waterfront, and Bonaire’s marine parks. During the holiday season, the islands come alive with festive cheer—wander through streets lined with twinkling lights, admire palm trees wrapped in glowing strands, and soak in the tropical spirit of Christmas with local music and open-air celebrations. Spend a festive Christmas Eve in St. George's Grenada, aglow with lights and island cheer, with time to explore its spice markets and waterfalls. Visit the untouched beaches of Mayreau and Bequia, the colonial charm of Basseterre, and the French flair of Les Saintes. Hike Dominica’s lush rainforests and explore Martinique’s Creole culture. Throughout your voyage, take full advantage of the Marina for kayaking, paddleboarding, and more.  Celebrate the season with Windstar’s holiday traditions, including Christmas high tea and brunch, a festive New Year’s Eve party, and possible fireworks in Les Saintes.
voyage map
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Day 1: Oranjestad
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
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Day 2: Willemstad
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
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Day 3: Kralendijk
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
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Day 5: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 6: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 7: 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 8: 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 9: 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 11: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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Day 12: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 13: Roseau
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.
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Day 14: 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 15: Fort-de-France
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Day 16: 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
Basseterre
In Basseterre, explore the historic Brimstone Hill Fortress, a UNESCO World Heritage Site, offering panoramic views of the island and sea.
Dominica
Take a hike in Dominica’s Morne Trois Pitons National Park, a UNESCO site and see Trafalgar Waterfalls.
laundry
Pack light with complimentary daily laundry service   
Mayreau
Visit Mayreau, the smallest island of the Grenadines and enjoy the exclusive Signature Beach Party.
St. George’s
An overnight and late-night stay in St. George’s, Grenada gives you plenty of time to explore the Annandale Waterfall and shop for spices – Grenada is known as the “Isle of Spice.”
Willemstad
Your late-night stay in Willemstad lets you explore the brightly colored architecture of this UNESCO site in the day and the lights at night.
Windstar’s Christmas High Tea
A true holiday highlight is Windstar’s Christmas High Tea, featuring Christmas Cake and Stollen. Served in Compass Rose, the Lounge, or even on open deck if weather allows, this elegant affair is often accompanied by a local band.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Dec 20
Oranjestad
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Dec 21
Willemstad
Arrive:  9:00 AM
Depart:  9:00 PM
Watersports Platform: 
Mon Dec 22
Kralendijk
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Dec 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Dec 24
St. George's
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Thu Dec 25
St. George's
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 26
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Dec 27
Bequia
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Dec 28
Bridgetown
Arrive:  5:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Dec 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Dec 30
Basseterre
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Dec 31
Les Saintes
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 1
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Fri Jan 2
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 3
Fort-de-France
Arrive:  7:30 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jan 4
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.
? Call for Availability
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
? Call for Availability
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.
? Call for Availability
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.
? Call for Availability
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.
? Call for Availability
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.
? 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
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
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Holiday Sailings
Thankful For Travel Sales Event
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, Dec 20 - Sun, Jan 4, 2026
WIND SPIRIT
Call For Availability
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SAILING