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Star Collector: The Best Of The Windward & Leeward Isles

Ship: Wind Surf   
Departure: Sunday, January 4, 2026
Nights: 28 nights
One Way Trip
One
way trip
Duration
28
Nights
Days at Sea
4
Sea Days
Ports
20
Ports
Countries Visted
17
Countries
  • Itinerary

    Star Collector: The Best Of The Windward & Leeward Isles

    Ports of call

    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
    View of St Martin (Philipsburg), Sint Maarten (Dutch part)

    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)

    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

    3 Tuesday, January 6, 2026 Road Bay
    4 Wednesday, January 7, 2026 Sopers Hole, Virgin Islands (British) 08:00 18:00

    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)

    4 Wednesday, January 7, 2026 San Juan, Puerto Rico 19:00 23:59
    View of San Juan, Puerto Rico

    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

    5 Thursday, January 8, 2026 San Juan, Puerto Rico 22:00
    View of San Juan, Puerto Rico

    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

    6 Friday, January 9, 2026 Virgin Gorda, Virgin Islands (British) 08:00 17:00
    View of Virgin Gorda, Virgin Islands (British)

    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)

    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
    View of St Martin (Philipsburg), Sint Maarten (Dutch part)

    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)

    9 Monday, January 12, 2026 Basseterre, Saint Kitts and Nevis 07:00 22:00
    View of Basseterre, Saint Kitts and Nevis

    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

    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

    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

    13 Friday, January 16, 2026 Roseau, Dominica 08:00 17:00
    View of Roseau, Dominica

    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

    14 Saturday, January 17, 2026 Pigeon Island, Saint Lucia 07:00 16:00
    View of Pigeon Island, Saint Lucia

    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

    15 Sunday, January 18, 2026 Bridgetown, Barbados 05:00 18:00
    View of Bridgetown, Barbados

    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

    16 Monday, January 19, 2026 Anse Mitan, Martinique 09:00 23:00

    Anse Mitan (Mitan Cove) is located just to the west of the town of Les Trois-Îlets, on the SW coast of the island Martinique, a French region in the Lesser Antilles in the Caribbean Sea. The cove is adjacent to Pointe du Bout (‘Land’s End’), in one of the most popular tourist destinations on the island. The cove has a half-kilometre curved and narrow sandy beach with calm water, backing onto a 200m wide isthmus. Read more about Anse Mitan, Martinique

    17 Tuesday, January 20, 2026 Castries, Saint Lucia 08:00 16:00
    View of Castries, Saint Lucia

    Castries is the capital of the volcanic island country of Saint Lucia, part of the Lesser Antilles in the eastern Caribbean Sea. Its popularity stems from the tropical weather (the dry season runs from December through May), scenery, and numerous beaches. Saint Lucia's population is predominantly of African and mixed African-European descent, and while the official language is English, French-Creole is spoken by 95% of the population. Read more about Castries, Saint Lucia

    17 Tuesday, January 20, 2026 Pigeon Island, Saint Lucia 18:00 23:59
    View of Pigeon Island, Saint Lucia

    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

    18 Wednesday, January 21, 2026 Pigeon Island, Saint Lucia 18:00
    View of Pigeon Island, Saint Lucia

    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

    19 Thursday, January 22, 2026 Bequia, Saint Vincent and the Grenadines 08:00 22:00
    View of Bequia, Saint Vincent and the Grenadines

    Saint Vincent and the Grenadines is a country of 32 beautiful Caribbean islands in the idyllic Caribbean, stretching south from Saint Vincent Island to Grenada. Proud of its French and British colonial history, it is now part of the Commonwealth of Nations and the Caribbean Community of 15 nations. Bequia (pronounced "Beck-way”) is blessed with white sandy beaches, coral reefs, and friendly people. Read more about Bequia, Saint Vincent and the Grenadines

    20 Friday, January 23, 2026 Mayreau, Saint Vincent and the Grenadines 08:00 18:00
    View of Mayreau, Saint Vincent and the Grenadines

    Mayreau is the smallest inhabited island of the Grenadines, in the far SE of the Caribbean Sea. It has a population of about 300, centred at the Old Wall village, with its small school, a telecommunications building, and the Mayreau Catholic Church located on a hilltop in the SW of the island. With its picture-postcard beaches, it truly is a secret treasure of peace and tranquillity. Read more about Mayreau, Saint Vincent and the Grenadines

    21 Saturday, January 24, 2026 St George's, Grenada 07:00 14:00
    View of St George's, Grenada

    St. George's is the capital of Grenada, British West Indies. The city surrounds a horseshoe-shaped harbour, and is an attractive colonial-era town with a distinctly Mediterranean feel that appears to spill down the hill side. Read more about St George's, Grenada

    22 Sunday, January 25, 2026 Bridgetown, Barbados 06:00 18:00
    View of Bridgetown, Barbados

    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

    23 Monday, January 26, 2026 Man-O-War Bay
    24 Tuesday, January 27, 2026 Mayreau, Saint Vincent and the Grenadines 08:00 18:00
    View of Mayreau, Saint Vincent and the Grenadines

    Mayreau is the smallest inhabited island of the Grenadines, in the far SE of the Caribbean Sea. It has a population of about 300, centred at the Old Wall village, with its small school, a telecommunications building, and the Mayreau Catholic Church located on a hilltop in the SW of the island. With its picture-postcard beaches, it truly is a secret treasure of peace and tranquillity. Read more about Mayreau, Saint Vincent and the Grenadines

    25 Wednesday, January 28, 2026 Soufriere
    26 Thursday, January 29, 2026 At Sea
    27 Friday, January 30, 2026 Kralendijk, Bonaire, Bonaire, Sint Eustatius and Saba 13:00 22:00
    28 Saturday, January 31, 2026 Willemstad, Curaçao, Curaçao 08:00 18:00
    29 Sunday, February 1, 2026 Oranjestad, Aruba, Aruba 06:00 Disembark
    View of Oranjestad, Aruba, Aruba

    In the southern Caribbean, Oranjestad is the capital of the small island of Aruba, and an island territory of the Kingdom of the Netherlands. It is an attractive and historic harbour town just 27 km north of Venezuela. It can be divided into Upper and Lower Towns. Read more about Oranjestad, Aruba, Aruba

  • Ship

    Wind Surf Overview

    Wind Surf

    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.

  • Cabins

    Wind Surf Cabins

    Bridge Suite

    Bridge Suite

    Bridge Suite on the Wind Surf Bridge Suite on the Wind Surf

    Cabin Types

    brs, BS

    Average Cabin Size – 0 m2

    Average Balcony Size – 0 m2

    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.

    Suite

    Suite

    Suite on the Wind Surf Suite on the Wind Surf

    Cabin Types

    ste, Owner, OS

    Average Cabin Size – 0 m2

    Average Balcony Size – 0 m2

    Size: 242-376 square feet (22.5-35 square meters). Some Suites have 2 bathrooms.

    Oceanview

    Oceanview

    Oceanview on the Wind Surf Oceanview on the Wind Surf

    Cabin Types

    TX, BX, AX, B, A

    Average Cabin Size – 0 m2

    Average Balcony Size – 0 m2

    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.

    Guarantee

    Guarantee

    Guarantee on the Wind Surf Guarantee on the Wind Surf

    Cabin Types

    Y

    Average Cabin Size – 0 m2

    Average Balcony Size – 0 m2

    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.

  • Deck Plans

    Deck Plans for Wind Surf

    Legend

    • Restricted View
    • Adjoining Suites
    • Elevator
    • Modified Accessible Suites
    • One queen size bed only
    • Shower only
    • Shower only (Star Legend)
  • Promotions

    Current Cruise Deals for Wind Surf

    Windstar Cruises - Luxury inclusions

    Windstar Cruises - Luxury inclusions

    Windstar Luxury Inclusions:
    • Open dining with no reservations required
    • Non-alcoholic beverages, including coffee, tea and soda
    • Beautifully appointed ocean-view staterooms and suites
    • Plush bathrobes and slippers
    • Fresh flowers and fruit in your stateroom or suite
    • Newly renovated marble bathrooms
    • Flat-screen TV with DVD player
    • Spectacular onboard barbecue*
    • Onboard entertainment, including local performances in most regions
    • Room service
    • Fully equipped water-sports platform and use of all water-sports equipment*
    • Access to the open bridge
    • Champagne welcome reception
    • Beautiful sail-away from every port*
    • Access to WorldSpa by Windstar facilities and fitness classes
    *Depending on port and weather conditions

    Terms & Conditions apply.

Cabin Availability

Hold a cabin or view live cabin availability aboard Wind Surf for this sailing

Guarantee at the Wind Surf

Guarantee

Sold out
Oceanview at the Wind Surf

Oceanview

From $15317
Suite at the Wind Surf

Suite

Sold out
Bridge Suite at the Wind Surf

Bridge Suite

Sold out

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  • Star Collector: The Best Of The Windward & Leeward Isles

    Cruiseline: Windstar Ship: Wind Surf Departure: Sunday, January 4, 2026 Nights: 28 nights Departs: St Martin (Philipsburg) Returns: Oranjestad, Aruba

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