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Call Your Travel Advisor or
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Beach Fun & Sun: A Remote Caribbean Getaway
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sun Dec 14, 2025 - Sun Dec 21, 2025,
7 days
on Wind Surf
VIEW ALL DATES
Starting from
$2,399 USD
BOOK NOW
REQUEST A QUOTE
OVERVIEW & ITINERARY
OVERVIEW
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VIEW THE JOURNEY
Philipsburg, St. Maarten to Philipsburg, 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.
VIEW THE JOURNEY
Day 1: Philipsburg, 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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 6: Virgin Gorda / Prickly Pear, British Virgin Islands
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. Although 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.
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 8: Philipsburg, 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
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Let the Bubbly Pool on Jost Van Dyke wash your cares away.
Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s
Treasure Island
Soak in the natural bathing pools of "The Baths" at Virgin Gorda.
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach
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
WatersportsPlatform
Watersports Platform:
Sun Dec 14
Philipsburg, St. Maarten
Arrive:
Depart:
7:00 PM
Watersports Platform:
Mon Dec 15
Falmouth Harbour
Arrive:
8:00 AM
Depart:
6:00 PM
Watersports Platform:
Tue Dec 16
Road Bay
Arrive:
8:00 AM
Depart:
6:00 PM
Watersports Platform:
Wed Dec 17
Soper's Hole
Arrive:
8:00 AM
Depart:
6:00 PM
Watersports Platform:
Wed Dec 17
Jost Van Dyke, Great Harbour
Arrive:
7:00 PM
Depart:
Watersports Platform:
Thu Dec 18
Jost Van Dyke, Great Harbour
Arrive:
Depart:
10:00 PM
Watersports Platform:
Fri Dec 19
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:
8:00 AM
Depart:
5:00 PM
Watersports Platform:
Sat Dec 20
Gustavia
Arrive:
8:00 AM
Depart:
10:00 PM
Watersports Platform:
Sun Dec 21
Philipsburg, St. Maarten
Arrive:
6:00 AM
Depart:
Watersports Platform:
SEE EXPANDED ITINERARY AND SHORE EXCURSIONS
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.
LEARN MORE →
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
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
$2,399
per guest
?
All-inclusive price from
$3,092
per guest
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
$2,599
per guest
?
All-inclusive price from
$3,292
per guest
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
$2,699
per guest
?
All-inclusive price from
$3,392
per guest
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
$2,899
per guest
?
All-inclusive price from
$3,592
per guest
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
$3,299
per guest
?
All-inclusive price from
$3,992
per guest
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
$5,299
per guest
?
All-inclusive price from
$5,992
per guest
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
$5,499
per guest
?
All-inclusive price from
$6,192
per guest
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
$6,599
per guest
?
All-inclusive price from
$7,292
per guest
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.
SEE WINDSTAR LIFE →
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
7-for-7
Holiday Sailings
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Every Thursday, enjoy new deals on amazing voyages — valid for 7 days or until sold out! Not combinable with other promotions.
Terms & Conditions
apply.
A Windstar cruise is always a special occasion, but join us at Thanksgiving, Christmas, Hanukkah, or New Year’s and you’ll find us at our festive best.
Our lowest fares for cruises departing soon! Pack your bags NOW!
Windstar’s Pick Your Perk offer is back for another season of savings. With options that match your travel style, you get to make the most of your vacation, your way. Reserve a cruise departing through June 2026 and you'll get to choose between an onboard credit, a hotel stay or — for Premium Suite guests — an All-Inclusive package.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Dec 28 - Sat, Jan 4, 2025
WIND SURF
$4,792
$4,099
VIEW
SAILING
Sat, Jan 11 - Sat, Jan 18, 2025
WIND SURF
$3,251
$2,558
VIEW
SAILING
Sat, Jan 25 - Sat, Feb 1, 2025
WIND SURF
$3,581
$2,888
VIEW
SAILING
Sat, Feb 1 - Sat, Feb 8, 2025
WIND SURF
$4,292
$3,599
VIEW
SAILING
Sat, Feb 15 - Sat, Feb 22, 2025
WIND SURF
$3,451
$2,758
VIEW
SAILING
Sat, Mar 1 - Sat, Mar 8, 2025
WIND SURF
$3,892
$3,199
VIEW
SAILING
Sat, Mar 8 - Sat, Mar 15, 2025
WIND SURF
$3,171
$2,478
VIEW
SAILING
Sat, Mar 22 - Sat, Mar 29, 2025
WIND SURF
$3,892
$3,199
VIEW
SAILING
Sun, Dec 14 - Sun, Dec 21, 2025
WIND SURF
$3,092
$2,399
THIS
SAILING
Sun, Dec 28 - Sun, Jan 4, 2026
WIND SURF
$3,392
$2,699
VIEW
SAILING
Sun, Jan 4 - Sun, Jan 11, 2026
WIND SURF
$3,292
$2,599
VIEW
SAILING
Sat, Jan 24 - Sat, Jan 31, 2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat, Jan 31 - Fri, Feb 6, 2026
WIND SPIRIT
Call For Availability
VIEW
SAILING
Sat, Feb 14 - Sat, Feb 21, 2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat, Feb 21 - Sat, Feb 28, 2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat, Mar 7 - Sat, Mar 14, 2026
WIND SURF
$3,392
$2,699
VIEW
SAILING
Sat, Mar 14 - Sat, Mar 21, 2026
WIND SURF
$3,092
$2,399
VIEW
SAILING
Sat, Mar 28 - Sat, Apr 4, 2026
WIND SURF
$3,092
$2,399
VIEW
SAILING
Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 days
Close
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Falmouth Harbour
Day 3
Road Bay
Day 4
Soper's Hole
Day 4
Jost Van Dyke, Great Harbour
Day 5
Jost Van Dyke, Great Harbour
Day 6
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
ALL DATES &
FARES
7-for-7
Holiday Sailings
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Every Thursday, enjoy new deals on amazing voyages — valid for 7 days or until sold out! Not combinable with other promotions.
Terms & Conditions
apply.
A Windstar cruise is always a special occasion, but join us at Thanksgiving, Christmas, Hanukkah, or New Year’s and you’ll find us at our festive best.
Our lowest fares for cruises departing soon! Pack your bags NOW!
Windstar’s Pick Your Perk offer is back for another season of savings. With options that match your travel style, you get to make the most of your vacation, your way. Reserve a cruise departing through June 2026 and you'll get to choose between an onboard credit, a hotel stay or — for Premium Suite guests — an All-Inclusive package.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat
Dec 28
2024
WIND SURF
$4,792
$4,099
VIEW
SAILING
Sat
Jan 11
2025
WIND SURF
$3,251
$2,558
VIEW
SAILING
Sat
Jan 25
2025
WIND SURF
$3,581
$2,888
VIEW
SAILING
Sat
Feb 1
2025
WIND SURF
$4,292
$3,599
VIEW
SAILING
Sat
Feb 15
2025
WIND SURF
$3,451
$2,758
VIEW
SAILING
Sat
Mar 1
2025
WIND SURF
$3,892
$3,199
VIEW
SAILING
Sat
Mar 8
2025
WIND SURF
$3,171
$2,478
VIEW
SAILING
Sat
Mar 22
2025
WIND SURF
$3,892
$3,199
VIEW
SAILING
Sun
Dec 14
2025
WIND SURF
$3,092
$2,399
VIEW
SAILING
Sun
Dec 28
2025
WIND SURF
$3,392
$2,699
VIEW
SAILING
Sun
Jan 4
2026
WIND SURF
$3,292
$2,599
VIEW
SAILING
Sat
Jan 24
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Jan 31
2026
WIND SPIRIT
Call For Availability
VIEW
SAILING
Sat
Feb 14
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Feb 21
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Mar 7
2026
WIND SURF
$3,392
$2,699
VIEW
SAILING
Sat
Mar 14
2026
WIND SURF
$3,092
$2,399
VIEW
SAILING
Sat
Mar 28
2026
WIND SURF
$3,092
$2,399
VIEW
SAILING
Click on the date to view the map and itinerary by date
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