Classic Caribbean
 
St. Maarten to St. Maarten
Sat Mar 25, 2023 - Sat Apr 1, 2023,
 7 days
 on Wind Surf
?All-inclusive from
$2,422
?Cruise Only From
$1,799
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St. Maarten to St. Maarten
From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
voyage map
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Day 1: St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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Day 2: Charlestown
This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
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Day 3: 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 4: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 5: 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 6: 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 7: Gustavia
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by. 
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Day 8: St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Popular Highlights
Beach Party
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Les Saintes
Savor the distinctive French charm of enchanting Les Saintes.
Pigeon Island
Anchor alongside the pristine beaches of Pigeon Island’s 40-acre national park and explore at your leisure.
Sea Turtle Tagging
Enjoy the unspoiled paradise of Pinney’s Beach where Nevis volunteers tag sea turtles at night.
St. Kitts
Embrace the island life on St. Kitt's one-of-a-kind Shipwreck Beach.
Twin Pitons
Discover St. Lucia’s UNESCO site when you see the twin Pitons, rising majestically from the turquoise sea.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Mar 25
St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 26
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Mar 27
Roseau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Mar 28
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Mar 29
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Mar 30
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Mar 31
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Apr 1
St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
WINDSTAR SIGNATURE
A Complimentary Windstar Destination Discovery Event

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

Your private feast on the beach promises to be extraordinary. The menu has been carefully selected by Windstar's executive chef and is sure to please and tantalize your palate.

When your meal is complete and the stars begin to shine, the highlight of this enchanted evening will begin. Fire dancing has long been deeply embedded in the Polynesian culture as a way to send messages to the gods. Your fire dancing experts will be wearing traditional loincloths and will dazzle you with high-speed acrobatic moves, throwing flames so hot you'll feel the warmth 10 feet away.

Please note: This DestinationDiscovery Event has been scheduled in a way that will allow you to book and experience another shore excursion on the same day and you will not miss anything.

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $1,799 per guest
? All-inclusive price from $2,422 per guest
Category BX Deluxe
Category BX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $1,899 per guest
? All-inclusive price from $2,522 per guest
Category A
Category A
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $1,999 per guest
? All-inclusive price from $2,622 per guest
Category AX Deluxe
Category AX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $1,999 per guest
? All-inclusive price from $2,622 per guest
Category TX Deluxe
Category TX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,099 per guest
? All-inclusive price from $2,722 per guest
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.
? Cruise only from $4,499 per guest
? All-inclusive price from $5,122 per guest
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? Cruise only from $6,099 per guest
? All-inclusive price from $6,722 per guest
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
ALL DATES &
FARES
Last Minute Cruise Deals
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Mar 25 - Sat, Apr 1, 2023
WIND SURF
$2,422
$1,799
THIS
SAILING
Sat, Dec 9 - Sat, Dec 16, 2023
WIND SURF
$2,822
$2,199
Sat, Dec 23 - Sat, Dec 30, 2023
WIND SURF
$3,222
$2,599
Sat, Jan 6 - Sat, Jan 13, 2024
WIND SURF
$2,822
$2,199
Sat, Jan 20 - Sat, Jan 27, 2024
WIND SURF
$2,822
$2,199
Sat, Feb 3 - Sat, Feb 10, 2024
WIND SURF
$2,822
$2,199
Sat, Feb 17 - Sat, Feb 24, 2024
WIND SURF
$2,822
$2,199
Sat, Mar 2 - Sat, Mar 9, 2024
WIND SURF
$2,822
$2,199
Sat, Mar 16 - Sat, Mar 23, 2024
WIND SURF
$2,822
$2,199
! ITINERARY CHANGE St. Maarten TO St. Maarten 7 days on Wind Surf X
Please note: The ports in this itinerary have been updated as of XX/XX/XXXX
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Sat Mar 25
St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 26
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Mar 27
Roseau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Mar 28
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Mar 29
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Mar 30
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Mar 31
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Apr 1
St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: