Hold times may be longer than usual: We're currently undergoing a reservation system upgrade and are still fixing some issues. Please contact us if you have any questions.
Classic Caribbean
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Feb 8, 2025 - Sat Feb 15, 2025,
 7 days
 on Wind Surf
?All-inclusive from
$3,522
?Cruise Only From
$2,899
VIEW ALL SAILING
DATES & FARES
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
Philipsburg, St. Maarten to Philipsburg, 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
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 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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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.
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
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 Feb 8
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Feb 10
Roseau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 11
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 12
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Feb 13
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Feb 14
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Feb 15
Philipsburg, 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.
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
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 $2,899 per guest
? All-inclusive price from $3,522 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 $3,139 per guest
? All-inclusive price from $3,762 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 $3,199 per guest
? All-inclusive price from $3,822 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 $3,499 per guest
? All-inclusive price from $4,122 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 $3,849 per guest
? All-inclusive price from $4,472 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 $5,899 per guest
? All-inclusive price from $6,522 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 $6,099 per guest
? All-inclusive price from $6,722 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.
? 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
Complimentary All-Inclusive Upgrade
Holiday Sailings
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, Dec 21 - Sat, Dec 28, 2024
WIND SURF
$2,999
$2,999
Sat, Jan 4 - Sat, Jan 11, 2025
WIND SURF
$3,222
$2,599
Sat, Jan 18 - Sat, Jan 25, 2025
WIND SURF
$3,422
$2,799
Sat, Feb 8 - Sat, Feb 15, 2025
WIND SURF
$3,522
$2,899
THIS
SAILING
Sat, Feb 22 - Sat, Mar 1, 2025
WIND SURF
$3,222
$2,599
Sat, Mar 15 - Sat, Mar 22, 2025
WIND SURF
$3,322
$2,699
Sun, Dec 7 - Sun, Dec 14, 2025
WIND SURF
$2,922
$2,299
Sun, Dec 21 - Sun, Dec 28, 2025
WIND SURF
$3,322
$2,699
Sat, Feb 7 - Sat, Feb 14, 2026
WIND SPIRIT
$3,222
$2,599
Sat, Feb 28 - Sat, Mar 7, 2026
WIND SURF
$2,922
$2,299
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SURF
Call For Availability