To find out more about the itinerary for this cruise, select the itinerary items below.
| Day | Date | Port of Call | Arrival | Departure |
|---|---|---|---|---|
| 1 | Sunday, January 4, 2026 | St Martin (Philipsburg), Sint Maarten (Dutch part) | Embark | 19:00 |
The island is shared in two parts as: the northern part Saint-Martin (a French overseas collectivity) and southern part Sint Maarten (of the Kingdom of the Netherlands): hence its name St-Martin / St Maarten. It lies in the NE Caribbean, located 300 km E of Puerto Rico. This tiny island is an extremely popular holiday and duty-free shopping destination famous for its variety of 37 palm-treed beaches that include salt-water ponds. Read more about St Martin (Philipsburg), Sint Maarten (Dutch part) |
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| 2 | Monday, January 5, 2026 | Falmouth, Antigua and Barbuda | 08:00 | 18:00 |
Falmouth is a coastal town on the SW of the island of Antigua, one half of the twin-island nation of Antigua and Barbuda in the Leeward Islands, Eastern Caribbean. The country was named by Christopher Columbus in 1493. (In September 2017 Barbuda, 42 km to the north, was 95% decimated by Hurricane Irma.) Falmouth lies aside one of the many natural harbours on Antigua’s shoreline. Read more about Falmouth, Antigua and Barbuda |
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| 3 | Tuesday, January 6, 2026 | Road Bay | ||
| 4 | Wednesday, January 7, 2026 | Sopers Hole, Virgin Islands (British) | 08:00 | 18:00 |
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Soper's Hole is a small settlement on the secluded south-west tip of Tortola, the largest and most populated of the British Virgin Islands. Tortola is a tax haven and home to many offshore companies that do business worldwide with many workers coming from other Caribbean islands. Read more about Sopers Hole, Virgin Islands (British) |
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| 4 | Wednesday, January 7, 2026 | San Juan, Puerto Rico | 19:00 | 23:59 |
San Juan, the capital and most populous city of Puerto Rico, is the oldest city on US territory. It is the Caribbean commercial hub, best known for its beautifully restored historic district of Old San Juan. It is situated on a rocky peninsula girded by thick walls jutting into the crashing Atlantic surf. Read more about San Juan, Puerto Rico |
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| 5 | Thursday, January 8, 2026 | San Juan, Puerto Rico | 22:00 | |
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San Juan, the capital and most populous city of Puerto Rico, is the oldest city on US territory. It is the Caribbean commercial hub, best known for its beautifully restored historic district of Old San Juan. It is situated on a rocky peninsula girded by thick walls jutting into the crashing Atlantic surf. Read more about San Juan, Puerto Rico |
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| 6 | Friday, January 9, 2026 | Virgin Gorda, Virgin Islands (British) | 08:00 | 17:00 |
Virgin Gorda (‘Fat Virgin’) is the third largest and the second most populated of the British Virgin Islands. The main business centre is Spanish Town, to the SW of this elongated island. Ships tender to port. Read more about Virgin Gorda, Virgin Islands (British) |
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| 7 | Saturday, January 10, 2026 | Gustavia, Saint Barthélemy | 08:00 | 22:00 |
| 8 | Sunday, January 11, 2026 | St Martin (Philipsburg), Sint Maarten (Dutch part) | 06:00 | 19:00 |
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The island is shared in two parts as: the northern part Saint-Martin (a French overseas collectivity) and southern part Sint Maarten (of the Kingdom of the Netherlands): hence its name St-Martin / St Maarten. It lies in the NE Caribbean, located 300 km E of Puerto Rico. This tiny island is an extremely popular holiday and duty-free shopping destination famous for its variety of 37 palm-treed beaches that include salt-water ponds. Read more about St Martin (Philipsburg), Sint Maarten (Dutch part) |
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| 9 | Monday, January 12, 2026 | Basseterre, Saint Kitts and Nevis | 07:00 | 22:00 |
Basseterre is located on the SW coast of St Kitts Island in the Leeward Islands group, and is one of the oldest towns in the Eastern Caribbean. Subsequently, it is very well known for its variety of architectural styles and fascinating buildings, set against dense tropical forests and a huge dormant volcano. The domed colonial Treasury Building, or customs house, is a reminder of the value of these islands as sugar colonies. Read more about Basseterre, Saint Kitts and Nevis |
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| 10 | Tuesday, January 13, 2026 | Montserrat, Montserrat | 08:00 | 18:00 |
Montserrat (‘Serrated Mountain’), also known as the ‘Emerald Isle of the Caribbean’, is a lush green volcanic island in the Leeward Islands of the NE Caribbean. It is a British Overseas Territory. The island is 16.5km N-S and10kmE-W, and one-third of its area is covered by lava flows from the 1995-2000 eruptions of Soufrière Hills volcano (French: “sulfur outlet”; 915m). Read more about Montserrat, Montserrat |
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| 11 | Wednesday, January 14, 2026 | Gustavia, Saint Barthélemy | 08:00 | 23:00 |
| 12 | Thursday, January 15, 2026 | Deshaies, Guadeloupe | 12:30 | 22:00 |
In the French overseas region and department of Guadeloupe, Deshaies is a commune located on the NW coast of Basse-Terre Island. It is situated on the deepest best naturally protected bay of all the Eastern Caribbean coast, and historically it was used as a shelter for the early explorers. Known as Fort Royal, it was the the first village of Club Med intended exclusively for American customers. Read more about Deshaies, Guadeloupe |
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| 13 | Friday, January 16, 2026 | Roseau, Dominica | 08:00 | 17:00 |
Roseau, a small, compact and most important urban settlement, is the capital and largest city of the island of Dominica, in the Caribbean. Dominica has been nicknamed the ‘Nature Isle of the Caribbean’ for its unspoiled natural beauty. Interestingly, it is built on the site of the ancient Kalinago Indian village of Sairi. Read more about Roseau, Dominica |
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| 14 | Saturday, January 17, 2026 | Pigeon Island, Saint Lucia | 07:00 | 16:00 |
Pigeon Island is a 40 acre islet with artificial causeway built in 1972 joining it to Gros Islet commune, on the northern tip of the island-country of Saint Lucia. Saint Lucia is part of the Lesser Antilles in the eastern Caribbean Sea. The island as a whole has switched hands between the British and French throughout its existence. Read more about Pigeon Island, Saint Lucia |
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| 15 | Sunday, January 18, 2026 | Bridgetown, Barbados | 05:00 | Disembark |
The city of Bridgetown is the capital and largest city of the island country of Barbados, a major tourist destination in the West Indies. The city has numerous attractions, landmarks, monuments, museums, and art galleries of an international standard. It is also a starting point for visiting many other popular cities on the island. Read more about Bridgetown, Barbados |
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Wind Surf is the flagship sailing ship of the of the Windstar fleet. With a capacity of 342 guests she is the worlds largest sailing ship. The vessel features six decks and a variety of amenities including a spa, fitness centre, multiple dining venues, and a casino. The cabins are spacious and well-appointed, with all the modern comforts of home. What sets Wind Surf apart from other ships is its impressive five-masted rigging, providing an unforgettable sailing experience.
brs, BS
Size: 495 square feet (46 square meters). 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.
ste, Owner, OS
Size: 242-376 square feet (22.5-35 square meters). Some Suites have 2 bathrooms.
TX, BX, AX, B, A
Size: 188 square feet (18 square meters). 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 Lrsquo;Occitanereg; 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. Note: Staterooms with 3rd Berths: 117ndash;139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.
Y
With this selection, you are guaranteed to receive a stateroom within a selected category, anywhere on the ship. However, the actual room assignment and location on the ship may be determined at any time after your reservation has been completed and paid in full up to the day of sailing.
Restricted View
Adjoining Suites
Elevator
Modified Accessible Suites
One queen size bed only
Shower only
Shower only (Star Legend)
Windstar Cruises - Luxury Inclusions
Windstar Luxury Inclusions:
• Open dining with no reservations required and room service
• Non-alcoholic beverages, including coffee, tea and soda
• Beautifully appointed ocean-view staterooms and suites with newly renovated marble bathrooms and flat-screen TV with DVD player
• Plush bathrobes and slippers and fresh flowers and fruit in your stateroom or suite
• Spectacular onboard barbecue (weather and port dependent)
• Onboard entertainment, including local performances in most regions
• Fully equipped water-sports platform and use of all water-sports equipment (weather and port dependant)
• Access to the open bridge
• Champagne welcome reception and beautiful sail-away from every port
• Access to WorldSpa by Windstar facilities and fitness classes
Terms & Conditions apply.
Hold a cabin or view live cabin availability aboard Wind Surf for this sailing
Speak to our team about your travel plans or book over the phone today!
1800 121 187
Cruiseline: Windstar Ship: Wind Surf Departure: Sunday, January 4, 2026 Nights: 14 nights Departs: St Martin (Philipsburg) Returns: Bridgetown
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