Beach Fun & Sun: A Remote Caribbean Getaway
 
St. Maarten to St. Maarten
Sat Jan 31, 2026 - Sat Feb 7, 2026,
 7 days
 on Wind Spirit
?All-inclusive from
$3,122
?Cruise Only From
$2,499
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St. Maarten to St. Maarten
Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
 
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: 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 romantic sunset Sail Away. 
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Day 2: 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 3: 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 4: Virgin Gorda / Prickly Pear
The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
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Day 5: 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 6: Road Bay
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
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Day 7: 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 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.
Jost Van Dyke
 Let the Bubbly Pool on Jost Van Dyke wash your cares away.
Normal Island
Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island
 
The Baths
Soak in the natural bathing pools of "The Baths" at Virgin Gorda.
Pusser's Landing/Soper's Hole
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach
 
Tortola/Road Bay
Find your beautiful spot on the beach while you sample some of the most delicious rum punch found in the Caribbean at Road Bay
 
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Jan 31
St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 1
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 1
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Mon Feb 2
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 3
Virgin Gorda / Prickly Pear
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 4
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 5
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Feb 6
Falmouth Harbour
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Feb 7
St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Wind Spirit
The Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht.
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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
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 $3,122 per guest
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.
? Cruise only from $2,699 per guest
? All-inclusive price from $3,322 per guest
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.
? Cruise only from $2,799 per guest
? All-inclusive price from $3,422 per guest
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.
? Cruise only from $2,999 per guest
? All-inclusive price from $3,622 per guest
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.
? Cruise only from $5,999 per guest
? All-inclusive price from $6,622 per guest
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
? 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
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Holiday Sailings
DISCOVER WINDSTAR’S DEGREES OF DIFFERENCE
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 24 - Sat, Mar 2, 2024
WIND SURF
$3,222
$2,599
Sat, Mar 9 - Sat, Mar 16, 2024
WIND SURF
$6,122
$5,499
Sat, Mar 23 - Sat, Mar 30, 2024
WIND SURF
$2,822
$2,199
Sat, Dec 28 - Sat, Jan 4, 2025
WIND SURF
$3,322
$2,699
Sat, Jan 11 - Sat, Jan 18, 2025
WIND SURF
$2,922
$2,299
Sat, Jan 25 - Sat, Feb 1, 2025
WIND SURF
$2,822
$2,199
Sat, Feb 1 - Sat, Feb 8, 2025
WIND SURF
$2,822
$2,199
Sat, Feb 15 - Sat, Feb 22, 2025
WIND SURF
$2,822
$2,199
Sat, Mar 1 - Sat, Mar 8, 2025
WIND SURF
$2,822
$2,199
Sat, Mar 8 - Sat, Mar 15, 2025
WIND SURF
$2,822
$2,199
Sat, Mar 22 - Sat, Mar 29, 2025
WIND SURF
$2,922
$2,299
Sun, Dec 14 - Sun, Dec 21, 2025
WIND SURF
$3,022
$2,399
Sun, Dec 28 - Sun, Jan 4, 2026
WIND SURF
$3,322
$2,699
Sun, Jan 4 - Sun, Jan 11, 2026
WIND SURF
$3,122
$2,499
Sat, Jan 24 - Sat, Jan 31, 2026
WIND SPIRIT
$3,122
$2,499
Sat, Jan 31 - Sat, Feb 7, 2026
WIND SPIRIT
$3,122
$2,499
THIS
SAILING
Sat, Feb 14 - Sat, Feb 21, 2026
WIND SPIRIT
$3,222
$2,599
Sat, Feb 21 - Sat, Feb 28, 2026
WIND SPIRIT
$3,222
$2,599
Sat, Mar 7 - Sat, Mar 14, 2026
WIND SURF
$3,022
$2,399
Sat, Mar 14 - Sat, Mar 21, 2026
WIND SURF
$3,022
$2,399
Sat, Mar 28 - Sat, Apr 4, 2026
WIND SURF
$3,022
$2,399