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Classic Caribbean
Windstar Cruises — Wind Surf

Classic Caribbean

From the lush volcanic landscapes of Nevis Peak to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the bes...

Departs Sun 06/02/2028
Duration 7 Nights
Ship Wind Surf
From Philipsburg
Region Caribbean
Day by Day

Ports of Call & Itinerary

7-night voyage departing Philipsburg.

Printable Itinerary (PDF)

Route Map

Classic Caribbean

7 ports plotted · click a marker for details

Day 1

Philipsburg , Sint Maarten (Dutch part)

Sunday, 06/02/2028

⚓ Arrives 08:00 🚢 Departs 19:00

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.

Philipsburg

Day 3

Roseau , Dominica

Tuesday, 08/02/2028

⚓ Arrives 08:00 🚢 Departs 16:00

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.

Roseau

Day 4

Mayreau Island , Saint Vincent and the Grenadines

Wednesday, 09/02/2028

⚓ Arrives 12:00 🚢 Departs 17:00

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Mayreau Island

Day 5

Terre-de-Haut , Guadeloupe

Thursday, 10/02/2028

⚓ Arrives 08:00 🚢 Departs 18:00

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.

Terre-de-Haut

Day 6

Basseterre, Saint Kitts , Saint Kitts and Nevis

Friday, 11/02/2028

⚓ Arrives 08:00 🚢 Departs 22:00

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.

Basseterre, Saint Kitts

Day 7

Gustavia , Saint Barthélemy

Saturday, 12/02/2028

⚓ Arrives 06:00 🚢 Departs 22:00

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.

Gustavia

Day 8

Philipsburg , Sint Maarten (Dutch part)

Sunday, 13/02/2028

⚓ Arrives 06:00

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.

Philipsburg
Choose Your Accommodation

Room Type & Prices

All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.

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Category B

Category B

188 sqft · Up to 2 guests

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...
✓ Toiletries Provided ✓ TV ✓ Wi-Fi (Additional Cost) ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost) ✓ Queen
Category BX Deluxe

Category BX Deluxe

188 sqft · Up to 2 guests

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...
✓ Toiletries Provided ✓ TV ✓ Wi-Fi (Additional Cost) ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost) ✓ Queen

Category BX Deluxe
Category A

Category A

188 sqft · Up to 2 guests

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...
✓ Toiletries Provided ✓ TV ✓ Wi-Fi (Additional Cost) ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost) ✓ Queen
Category AX Deluxe

Category AX Deluxe

188 sqft · Up to 2 guests

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...
✓ Queen or Twin Configuration ✓ Toiletries Provided ✓ TV ✓ Wi-Fi (Additional Cost) ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost)

Category AX Deluxe
Category TX Deluxe

Category TX Deluxe

188 sqft · Up to 2 guests

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...
✓ Toiletries Provided ✓ TV ✓ Wi-Fi (Additional Cost) ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost) ✓ Queen

Category TX Deluxe
Suite

Suite

376 sqft · Up to 3 guests

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.Amenities: SuiteQueen Size Be...
✓ Toiletries Provided ✓ TV ✓ Free Wi-Fi ✓ Coffee Machine ✓ Safe ✓ Hair Dryer ✓ Mini Bar (Additional Cost) ✓ Queen
Broadmoor Suite/Sea Island Suite Broadmoor Suite/Sea Island Suite Broadmoor Suite/Sea Island Suite Broadmoor Suite/Sea Island Suite Broadmoor Suite/Sea Island Suite

Broadmoor Suite/Sea Island Suite

495 sqft · Up to 3 guests

For Broadmoor Suite/Sea Island Suite: Enjoy 495 square feet of elevated comfort and refined style. Within this category, each suite embodies a unique design perspective inspired by two renowned Xanterra properties. Suite 503 draws inspiration from Sea Island, reflecting the relaxed coastal elegance and warm Southern ho...
✓ Queen or Twin Configuration ✓ Sofa Bed ✓ Dining Area ✓ Shower ✓ Whirlpool Bath ✓ Toiletries Provided ✓ Room Service Available ✓ Suite Benefits

Oceanview

Category B · 188 sqft

B

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Category BX Deluxe · 188 sqft

BX

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Category A · 188 sqft

A

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Category AX Deluxe · 188 sqft

AX

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Category TX Deluxe · 188 sqft

TX

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Suite

Suite · 376 sqft

STE

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Broadmoor Suite/Sea Island Suite · 495 sqft

BRS Bridge Suite

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Windstar Cruises

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Your Ship

Wind Surf

Windstar's Flagship Sailing Yacht

As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.

Wind Surf
342
Passengers
14,745
Gross Tonnage
1998
Year Built
6
Decks
171
Cabins
210
Crew

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