Yachtsman's Caribbean
 
St. Maarten to St. Maarten
Sat Mar 18, 2023 - Sat Mar 25, 2023,
 7 days
 on Wind Surf
?All-inclusive from
$2,322
?Cruise Only From
$1,699
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St. Maarten to St. Maarten
Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean’s private yachting scene. Explore the island charm of Road Town and the inviting beaches of Jost Van Dyke as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called "The Baths." Savor the high life on St. Barts.
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: Falmouth Harbour
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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Day 3:
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Day 4: Soper's Hole
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through “The Narrows.” 
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Day 4: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor. 
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Day 5: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor. 
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Day 5: Virgin Gorda
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina, Located to the south of Spanish Town lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
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Day 6: Virgin Gorda
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina, Located to the south of Spanish Town lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
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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
 Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share.
Jost Van Dyke
Relish extra beach time with late nights in both Jost Van Dyke and Virgin Gorda.
Sopers Hole
 Discover local treasures and island charm at Soper's Hole Wharf.
St. Barts
Beachcomb or mingle with the glitterati at St. Barts.
St. Maarten
 Shop and dine in duty-free St. Maarten
The Baths
Soak in the natural bathing pools of "The Baths" at Virgin Gorda.
Watersports Platform
 Sail, swim, and kayak off the Watersports Platform
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Mar 18
St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 19
Falmouth Harbour
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Mon Mar 20
AT SEA
Arrive:   N/A
Depart:   N/A
Watersports Platform: 
Tue Mar 21
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 21
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Wed Mar 22
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  3:00 PM
Watersports Platform: 
Wed Mar 22
Virgin Gorda
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Thu Mar 23
Virgin Gorda
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 24
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Mar 25
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 $1,699 per guest
? All-inclusive price from $2,322 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 $1,799 per guest
? All-inclusive price from $2,422 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 $1,799 per guest
? All-inclusive price from $2,422 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 $1,899 per guest
? All-inclusive price from $2,522 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 $1,999 per guest
? All-inclusive price from $2,622 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 $4,799 per guest
? All-inclusive price from $5,422 per guest
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
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.
? Call for Availability
ALL DATES &
FARES
Last Minute Cruise Deals
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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, Feb 18 - Sat, Feb 25, 2023
WIND SURF
$2,622
$1,999
Sat, Mar 18 - Sat, Mar 25, 2023
WIND SURF
$2,322
$1,699
THIS
SAILING
! 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 18
St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 19
Falmouth Harbour
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Mon Mar 20
AT SEA
Arrive:   N/A
Depart:   N/A
Watersports Platform: 
Tue Mar 21
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 21
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Wed Mar 22
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  3:00 PM
Watersports Platform: 
Wed Mar 22
Virgin Gorda
Arrive:  6:00 PM
Depart:  
Watersports Platform: 
Thu Mar 23
Virgin Gorda
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 24
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Mar 25
St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: