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Classic Caribbean
St. Maarten to St. Maarten
Sat Mar 25, 2023 - Sat Apr 1, 2023,
7 days
on Wind Surf
?
All-inclusive from
$2,422
?
Cruise Only From
$1,799
OVERVIEW & ITINERARY
OVERVIEW
LIFE ONBOARD
ITINERARY & SHORE EXCURSIONS
HOTELS
ACCOMMODATIONS & PRICING
VIEW ALL SAILING DATES & FARES
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VIEW THE JOURNEY
St. Maarten to 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.
VIEW THE JOURNEY
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: Charlestown
This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
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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.
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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.
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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.
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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.
VIEW THE JOURNEY
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
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Savor the distinctive French charm of enchanting Les Saintes.
Anchor alongside the pristine beaches of Pigeon Island’s 40-acre national park and explore at your leisure.
Enjoy the unspoiled paradise of Pinney’s Beach where Nevis volunteers tag sea turtles at night.
Embrace the island life on St. Kitt's one-of-a-kind Shipwreck Beach.
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
WatersportsPlatform
Watersports Platform:
Sat Mar 25
St. Maarten
Arrive:
Depart:
7:00 PM
Watersports Platform:
Sun Mar 26
Charlestown
Arrive:
8:00 AM
Depart:
5:00 PM
Watersports Platform:
Mon Mar 27
Roseau
Arrive:
8:00 AM
Depart:
5:00 PM
Watersports Platform:
Tue Mar 28
Pigeon Island
Arrive:
8:00 AM
Depart:
5:00 PM
Watersports Platform:
Wed Mar 29
Les Saintes
Arrive:
8:00 AM
Depart:
6:00 PM
Watersports Platform:
✓
Thu Mar 30
Basseterre
Arrive:
8:00 AM
Depart:
10:00 PM
Watersports Platform:
Fri Mar 31
Gustavia
Arrive:
8:00 AM
Depart:
10:00 PM
Watersports Platform:
✓
Sat Apr 1
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
$1,799
per guest
?
All-inclusive price from
$2,422
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
$1,899
per guest
?
All-inclusive price from
$2,522
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
$1,999
per guest
?
All-inclusive price from
$2,622
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
$1,999
per guest
?
All-inclusive price from
$2,622
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
$2,099
per guest
?
All-inclusive price from
$2,722
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
$4,499
per guest
?
All-inclusive price from
$5,122
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
$4,699
per guest
?
All-inclusive price from
$5,322
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
$6,099
per guest
?
All-inclusive price from
$6,722
per guest
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.
SEE WINDSTAR LIFE →
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
Last Minute Cruise Deals
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.
Our lowest fares for cruises departing soon! Pack your bags NOW!
Enjoy the freedom to Pick Your Perk. Choose between one free pre-or post-cruise Easy Stays hotel night, up to $1,000 Onboard Credit, or a free upgrade to an All-Inclusive Fare for Premium Suite guests, featuring Wi-Fi, unlimited beer, wine & cocktails and all gratuities.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Mar 25 - Sat, Apr 1, 2023
WIND SURF
$2,422
$1,799
THIS
SAILING
Sat, Dec 9 - Sat, Dec 16, 2023
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Dec 23 - Sat, Dec 30, 2023
WIND SURF
$3,222
$2,599
VIEW
SAILING
Sat, Jan 6 - Sat, Jan 13, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Jan 20 - Sat, Jan 27, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Feb 3 - Sat, Feb 10, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Feb 17 - Sat, Feb 24, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Mar 2 - Sat, Mar 9, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Mar 16 - Sat, Mar 23, 2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat, Dec 21 - Sat, Dec 28, 2024
WIND SURF
$3,622
$2,999
VIEW
SAILING
Sat, Jan 4 - Sat, Jan 11, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Jan 18 - Sat, Jan 25, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Jan 25 - Sat, Feb 1, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Feb 8 - Sat, Feb 15, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Feb 22 - Sat, Mar 1, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Mar 1 - Sat, Mar 8, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat, Mar 15 - Sat, Mar 22, 2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Classic Caribbean
Port to port
St. Maarten to St. Maarten
Duration
7 days
Close
Day
Port
Day 1
St. Maarten
Day 2
Charlestown
Day 3
Roseau
Day 4
Pigeon Island
Day 5
Les Saintes
Day 6
Basseterre
Day 7
Gustavia
Day 8
St. Maarten
ALL DATES &
FARES
Last Minute Cruise Deals
Seize Your Someday
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $89 per guest per day.
Our lowest fares for cruises departing soon! Pack your bags NOW!
Enjoy the freedom to Pick Your Perk. Choose between one free pre-or post-cruise Easy Stays hotel night, up to $1,000 Onboard Credit, or a free upgrade to an All-Inclusive Fare for Premium Suite guests, featuring Wi-Fi, unlimited beer, wine & cocktails and all gratuities.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat
Mar 25
2023
WIND SURF
$2,422
$1,799
THIS
SAILING
Sat
Dec 9
2023
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Dec 23
2023
WIND SURF
$3,222
$2,599
VIEW
SAILING
Sat
Jan 6
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Jan 20
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Feb 3
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Feb 17
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Mar 2
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Mar 16
2024
WIND SURF
$2,822
$2,199
VIEW
SAILING
Sat
Dec 21
2024
WIND SURF
$3,622
$2,999
VIEW
SAILING
Sat
Jan 4
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Jan 18
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Jan 25
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Feb 8
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Feb 22
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Mar 1
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Sat
Mar 15
2025
WIND SURF
$3,422
$2,799
VIEW
SAILING
Click on the date to view the map and itinerary by date