Beach Fun & Sun: A Remote Caribbean Getaway
 
St. Maarten to St. Maarten
Sat Dec 16, 2023 - Sat Dec 23, 2023,
 7 days
 on Wind Surf
?All-inclusive from
$2,922
?Cruise Only From
$2,299
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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: 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: 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 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 romantic sunset Sail Away. 
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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 6: 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 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.
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 Dec 16
St. Maarten
Arrive:
Depart:7:00 PM
Watersports Platform:  
Sun Dec 17
Falmouth Harbour
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform:  
Mon Dec 18
Road Bay
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
Tue Dec 19
Soper's Hole
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
Tue Dec 19
Jost Van Dyke, Great Harbour
Arrive:7:00 PM
Depart:
Watersports Platform: 
Wed Dec 20
Jost Van Dyke, Great Harbour
Arrive:
Depart:10:00 PM
Watersports Platform: 
Thu Dec 21
Virgin Gorda / Prickly Pear
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
Fri Dec 22
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
Sat Dec 23
St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform:  
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 $2,299 per guest
? All-inclusive price from $2,922 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 $2,499 per guest
? All-inclusive price from $3,122 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 $2,599 per guest
? All-inclusive price from $3,222 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 $2,799 per guest
? All-inclusive price from $3,422 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 $3,199 per guest
? All-inclusive price from $3,822 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 $5,199 per guest
? All-inclusive price from $5,822 per guest
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Cruise only from $5,399 per guest
? All-inclusive price from $6,022 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 $5,799 per guest
? All-inclusive price from $6,422 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.
Cooking Demonstrations
Open Bridge
Friendly and Relaxed Atmosphere
Local and Live Performances
Signature Sail Away
Crew Talent Show
Enjoy regionally inspired treatments at World Spa by Windstar
Take In The Sun
Complimentary 24 Hour Room Service
Relax at the Pool or Hot Tub
Relax With A Morning Yoga Session
Genuine and Thoughtful Crew
Signature Onboard Barbecue
Shopping With The Chef
Watersports Platform
ALL DATES &
FARES
Seize Your Someday
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, Nov 4 - Sat, Nov 11, 2023
STAR PRIDE
$3,022
$2,399
Sat, Dec 16 - Sat, Dec 23, 2023
WIND SURF
$2,922
$2,299
THIS
SAILING
Sat, Dec 30 - Sat, Jan 6, 2024
WIND SURF
$3,222
$2,599
Sat, Jan 13 - Sat, Jan 20, 2024
WIND SURF
$2,922
$2,299
Sat, Jan 27 - Sat, Feb 3, 2024
WIND SURF
$2,922
$2,299
Sat, Feb 10 - Sat, Feb 17, 2024
WIND SURF
$2,922
$2,299
Sat, Feb 24 - Sat, Mar 2, 2024
WIND SURF
$2,922
$2,299
Sat, Mar 9 - Sat, Mar 16, 2024
WIND SURF
$2,922
$2,299
Sat, Mar 23 - Sat, Mar 30, 2024
WIND SURF
$2,922
$2,299
Sat, Dec 28 - Sat, Jan 4, 2025
WIND SURF
$3,622
$2,999
Sat, Jan 11 - Sat, Jan 18, 2025
WIND SURF
$3,422
$2,799
Sat, Feb 1 - Sat, Feb 8, 2025
WIND SURF
$3,422
$2,799
Sat, Feb 15 - Sat, Feb 22, 2025
WIND SURF
$3,422
$2,799
Sat, Mar 8 - Sat, Mar 15, 2025
WIND SURF
$3,422
$2,799
Sat, Mar 22 - Sat, Mar 29, 2025
WIND SURF
$3,422
$2,799