Blue Waters of the Leeward Islands
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Wed Jan 14, 2026 - Sat Jan 24, 2026,
 10 days
 on Wind Spirit
?All-inclusive from
$4,489
?Cruise Only From
$3,599
VIEW ALL SAILING
DATES & FARES
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Explore the Leeward Islands of the Caribbean from panoramic summit views to sunny seashores and beneath azure waves during this 10-day cruise. Swim with gentle Antiqua stingrays near Falmouth Harbour. Take in expansive views of Martinique from the summit of Fort de France and admire colorful flowers in the quiet shade of small port Anse Mitan’s botanical garden. Learn how to crush local cocoa nibs into liquefied chocolate during a delicious chocolatier class in Castries on St. Lucia. Sail on a swift catamaran beyond Soper’s Hole and across turquoise waters to Norman Island, a lush and sandy setting that inspired Robert Lewis Stevenson’s classic Treasure Island. Extend your British Virgin Island shore explorations to include succulent lobster, grilled tuna and sweet rum cocktails during overnight port stays in Jost Van Dyke and Virgin Gorda. Remain comfortably dry while viewing colorful reef fish and coral during a semi-submersible cruise near Gustavia.
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 2: 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 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: Castries
The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.
VIEW THE JOURNEY
Day 5: Anse Mitan
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.
VIEW THE JOURNEY
Day 6: 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 7: 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.
VIEW THE JOURNEY
Day 8: 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. 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
VIEW THE JOURNEY
Day 9: 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 10: 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 11: 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
Anse Mitan
Take a tour of Anse Mitan’s Jardin de Balata Botanical Gardens with exotic plants from all over the world
Castries Market
Visit the Castries Market to peruse the handicrafts, fruits and vegetables.
Harrison’s Caves in Bridgetown
Explore Harrison’s Caves in Bridgetown.
Jost Van Dyke
Relish extra beach time with overnights in both Jost Van Dyke and Virgin Gorda.
Sopers Hole
Discover local treasures and island charm at Tortola’s Soper's Hole Wharf.
The Baths
Soak in Virgin Gorda’s The Baths natural bathing pools
Watersports Platform
Sail, swim, and kayak off the Watersports Platform directly off the back of the ship.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Wed Jan 14
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Thu Jan 15
Basseterre
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Fri Jan 16
Roseau
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Jan 17
Castries
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Jan 18
Anse Mitan
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 19
Les Saintes
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jan 20
Charlestown
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Wed Jan 21
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Jan 22
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Jan 23
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 24
Philipsburg, 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.
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
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 $3,599 per guest
? All-inclusive price from $4,489 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 $3,899 per guest
? All-inclusive price from $4,789 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 $4,099 per guest
? All-inclusive price from $4,989 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 $4,399 per guest
? All-inclusive price from $5,289 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 $7,099 per guest
? All-inclusive price from $7,989 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.
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
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
Wed, Jan 14 - Sat, Jan 24, 2026
WIND SPIRIT
$4,489
$3,599
THIS
SAILING