HomeSearchSt. Maarten to Bridgetown Wind Surf 2026-01-04
Wind Surf
Wind Surf
Captain-bridge
Compass-rose
Deck
Lounge
Lounge-bar
Pool-bar
Spa
Yacht-club-cafe
angelos-entrance
destination-briefings
live-music-duo
stella-bistro
veranda
yoga

St. Maarten to Bridgetown

  • 4th January 2026
  • 22 Nights
  • Philipsburg
  • Wind Surf
Windstar Cruises

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Balcony price from

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Outside price from

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Suite price from

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* based on twinshare stateroom

Call 13 70 79 Enquire

Your itinerary

  • Philipsburg, St. Martin
  • Falmouth, Antigua
  • Road Bay, Anguilla
  • Sopers Hole (Frenchmans Cay)
  • Great Harbour, Jost Van Dyke, B.V.I
  • Great Harbour, Jost Van Dyke, B.V.I
  • Virgin Gorda, B.V.I
  • Gustavia
  • Philipsburg, St. Martin
  • Basseterre, St. Kitts
  • Gustavia
  • Little Bay, Montserrat, Bwi
  • Gustavia
  • Deshaies, Guadeloupe
  • Roseau, Domimica
  • Pigeon Island, St.Lucia
  • Barbados
  • Anse Mitan, Martinique
  • Castries, St Lucia
  • Pigeon Island, St.Lucia
  • Bequia
  • Mayreau, Grenadines
  • St Georges, Grenada
  • Barbados
Day 1

4th Jan '26

Philipsburg, St. Martin
Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula. More
Less
Arrive

0:00

Depart

19:00

Day 2

5th Jan '26

Falmouth, Antigua
Surrounded by many abandoned sugar mills, the small village of Falmouth is protected in a large horseshoe-shaped bay. Falmouth was the first settlement on Antigua set up by the British. Today Falmouth is a quiet village surrounded by old sugar plantations and mills with the main historic building of interest being St Paul’s Church. The main center of activity in Falmouth Harbour is on the eastern side of the large horse-shoe bay where the shops, restaurants and marina are located. More
Less
Arrive

8:00

Depart

18:00

Day 3

6th Jan '26

Road Bay, Anguilla
Less
Arrive

8:00

Depart

18:00

Day 4

7th Jan '26

Sopers Hole (Frenchmans Cay)
Soper’s Hole Marina is arguably one of the most picturesque anchorage in the British Virgin Islands. More
Less
Arrive

8:00

Depart

18:00

Day 4

7th Jan '26

Great Harbour, Jost Van Dyke, B.V.I
Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don’t miss dining with your feet in the sand at Foxy’s on the beach-a perfect lunch stop! More
Less
Arrive

19:00

Depart

0:00

Day 5

8th Jan '26

Great Harbour, Jost Van Dyke, B.V.I
Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don’t miss dining with your feet in the sand at Foxy’s on the beach-a perfect lunch stop! More
Less
Arrive

0:00

Depart

22:00

Day 6

9th Jan '26

Virgin Gorda, B.V.I
The most chic resorts of the British Virgin Isles are located on Virgin Gorda, an eight-square-mile island divided nearly in two, with settlements at each end. The south of the island is best known for the curious assembly of house- sized rocks called “the Baths,” which are jumbled together to form huge underground pools and caverns. The beach at the Baths is large, wide, and sandy – perfect for sunning and swimming. More
Less
Arrive

8:00

Depart

17:00

Day 7

10th Jan '26

Gustavia
Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. More
Less
Arrive

8:00

Depart

22:00

Day 8

11th Jan '26

Philipsburg, St. Martin
Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula. More
Less
Arrive

6:00

Depart

0:00

Day 9

12th Jan '26

Basseterre, St. Kitts
Basseterre, set against the irresistible backdrop of St. Kitts’ emerald green hills and punctuated by elegant Georgian architecture, is one of the best of the Caribbean’s small capitals. More
Less
Arrive

8:00

Depart

21:00

Day 10

13th Jan '26

Gustavia
Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. More
Less
Arrive

8:00

Depart

22:00

Day 11

14th Jan '26

Little Bay, Montserrat, Bwi
Little Bay is a town under construction, intended to be the future capital of the Caribbean island of Montserrat. It is adjacent to Brades. More
Less
Arrive

8:00

Depart

22:00

Day 12

15th Jan '26

Gustavia
Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden. More
Less
Arrive

8:00

Depart

17:00

Day 13

16th Jan '26

Deshaies, Guadeloupe
Deshaies is a commune in the French overseas region and department of Guadeloupe, in the Lesser Antilles. It is on the northwest coast of Basse-Terre Island. The inhabitants are called Deshaisiens. More
Less
Arrive

8:00

Depart

17:00

Day 14

17th Jan '26

Roseau, Domimica
Roseau is the capital of the Caribbean island nation of Dominica. It’s on the southwest coast and known for its 18th-century Creole architecture. Its cobblestone Old Market, formerly a slave auction site, sells crafts and fruit. It’s next to the Dominica Museum, with exhibits on the country’s natural and cultural history. The Dominica Botanic Gardens showcase tropical flora and native Sisserou parrots. More
Less
Arrive

7:00

Depart

16:00

Day 15

18th Jan '26

Pigeon Island, St.Lucia
The twin towers of the Pitons, two volcanic peaks rising to more than 2,400 feet, mark St. Lucia, an island of lush green valleys, acres of banana plantations, and bubbling sulfur springs. 24 miles of vibrant reef make St. Lucia a haven for divers and snorkelers. Pigeon Island National Park, a 40-acre island connected to the mainland by a causeway, was once a pirates’ hideaway. Today, impressive ruins of old English forts, archaeological relics of Arawak Indians, and splendid beaches make this a fascinating place to explore. More
Less
Arrive

5:00

Depart

18:00

Day 16

19th Jan '26

Barbados
An infectiously happy island, with beautiful beaches, balmy weather, and a delightful British flair. As a result of its successful sugar economy in the 17th- to 19th-centuries, you’ll find large manor estates full of fine Barbados mahogany and antiques, along with gaily painted wooden frame houses– the essence of the festive Caribbean. Rum rules in Barbados, and, over the centuries, cane plantations have divided the Bajan landscape into a pretty patchwork of fields, coconut and royal palms, breadfruit, oleander, and citrus trees. More
Less
Arrive

8:00

Depart

0:00

Day 17

20th Jan '26

Anse Mitan, Martinique
Less
Arrive

0:00

Depart

6:00

Day 18

21st Jan '26

Castries, St Lucia
Castries is the capital of the island nation of St. Lucia, in the Caribbean Sea. It’s known for palm-lined Vigie Beach and as a port of call for cruise lines, with duty-free shopping near the harbor. The Cathedral Basilica of the Immaculate Conception, with its colorful murals, sits by leafy Derek Walcott Square park. Lively Castries Market is nearby. In the south, Morne Fortune hill offers views of the city More
Less
Arrive

8:00

Depart

18:00

Day 19

22nd Jan '26

Pigeon Island, St.Lucia
The twin towers of the Pitons, two volcanic peaks rising to more than 2,400 feet, mark St. Lucia, an island of lush green valleys, acres of banana plantations, and bubbling sulfur springs. 24 miles of vibrant reef make St. Lucia a haven for divers and snorkelers. Pigeon Island National Park, a 40-acre island connected to the mainland by a causeway, was once a pirates’ hideaway. Today, impressive ruins of old English forts, archaeological relics of Arawak Indians, and splendid beaches make this a fascinating place to explore. More
Less
Arrive

8:00

Depart

18:00

Day 20

23rd Jan '26

Bequia
Bequia is the second-largest island in the Grenadines at 7 square miles. It is part of the country of Saint Vincent and the Grenadines and is approximately 15 kilometres from the nation’s capital, Kingstown, on the main island, Saint Vincent. Bequia means “island of the clouds” in the ancient Arawak. More
Less
Arrive

8:00

Depart

22:00

Day 21

24th Jan '26

Mayreau, Grenadines
In the north of Mayreau is Salt Whistle Bay, a perfect half moon beach, separating the Atlantic from the Caribbean side with a sand spit only 50 yards wide, fringed by palm trees. The windward side of Mayreau is one huge deserted beach; you could spend days picnicking, sunbathing and snorkeling in the underwater world of Mayreau Garden. The southwestern, leeward beach is Saline Bay, nearly a mile of white sand with calm, clear water – ideal to bring your family! More
Less
Arrive

8:00

Depart

17:00

Day 22

25th Jan '26

St Georges, Grenada
St. George’s is the capital city of the Caribbean island of Grenada. In the town center, the 18th-century Fort George offers panoramic views of the island and St. George’s Bay. Nearby, Fort Matthew was formerly a battleground and, later, an asylum, and has underground tunnels. The Grenada National Museum hosts exhibits about the history of the region, including the plantation economy and the whaling industry. More
Less
Arrive

5:00

Depart

0:00

Day 23

26th Jan '26

Barbados
An infectiously happy island, with beautiful beaches, balmy weather, and a delightful British flair. As a result of its successful sugar economy in the 17th- to 19th-centuries, you’ll find large manor estates full of fine Barbados mahogany and antiques, along with gaily painted wooden frame houses– the essence of the festive Caribbean. Rum rules in Barbados, and, over the centuries, cane plantations have divided the Bajan landscape into a pretty patchwork of fields, coconut and royal palms, breadfruit, oleander, and citrus trees. More
Less
Arrive

0:00

Depart

0:00

Your ship - The 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.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Wind Surf
Captain-bridge
Compass-rose
Deck
Lounge
Lounge-bar
Pool-bar
Spa
Yacht-club-cafe
angelos-entrance
destination-briefings
live-music-duo
stella-bistro
veranda
yoga

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.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Library
Outdoor Pool

Hot Tubs
Massage
Spa
Whirlpool

Bar
Compass Rose
Degrees
Poolside Bar
Terrace Bar
Veranda

Description

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.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Recreational

Library
Outdoor Pool

Relaxation

Hot Tubs
Massage
Spa
Whirlpool

Food and Drink

Bar
Compass Rose
Degrees
Poolside Bar
Terrace Bar
Veranda

Staterooms

outside

Deluxe Stateroom

suite

Officers’ Suite

Stores

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Call 13 70 79 or enquire to book this cruise

Passenger first name limit

Due to cruise line restrictions for online bookings, we ask that passengers with first names exceeding 10 characters to please ring us on 1300 269 432 so we can help you complete your booking.

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Passenger last name limit

Due to cruise line restrictions for online bookings, we ask that passengers with last names exceeding 15 characters to please ring us on 1300 269 432 so we can help you complete your booking.

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Passenger name limit

Due to cruise line restrictions for online bookings, we ask that passengers with first names exceeding 10 characters and/or last names exceeding 15 characters to please ring us on 
1300 269 432 so we can help you complete your booking.

Close