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28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

Windstar

+1 more deal

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.

Windstar's WInd Surf sailing yacht at sea.

1 of 2

ABOARD

Wind Surf

4.7

18 reviews

Refurbished 2024

342 passengers

Built 1990

Windstar's WInd Surf sailing yacht at sea.

Cupecoy Beach with white resort buildings, St. Maarten.

Departing

Visiting

Philipsburg, St. Maarten, The Netherlands

22 Ports of Call

Sailing Jan 4, 2026

Call us for Pricing

Offramp

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Taxes & fees included

Taxes and fees included in all prices shown

Taxes and fees included in all prices shown

All special promotions on this sailing

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1 Sailing

2026

Prices from*

Taxes & fees included

Staterooms prices for Jan 4, 2026

Taxes and fees included in all prices shown

Taxes and fees included in all prices shown

Suite

Suite

published prices from

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for pricing

Contact Us to Book

Oceanview

Oceanview

published prices from

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for pricing

Contact Us to Book

Daily Itinerary

Sunday, January 4, 2026

Philipsburg, St. Maarten, The Netherlands

7:00 PM - 12:00 AM

Monday, January 5, 2026

Falmouth Harbour, Antigua

6:00 PM - 8:00 AM

Tuesday, January 6, 2026

Road Bay, Anguilla

6:00 PM - 8:00 AM

Wednesday, January 7, 2026

Sopers Hole, Tortola, British Virgin Islands

6:00 PM - 8:00 AM

Wednesday, January 7, 2026

Jost Van Dyke, British Virgin Islands

11:59 PM - 7:00 PM

Thursday, January 8, 2026

Jost Van Dyke, British Virgin Islands

10:00 PM - 12:00 AM

Friday, January 9, 2026

Virgin Gorda, British Virgin Islands

5:00 PM - 8:00 AM

Saturday, January 10, 2026

Gustavia, St. Barts

10:00 PM - 8:00 AM

Sunday, January 11, 2026

Philipsburg, St. Maarten, The Netherlands

7:00 PM - 6:00 AM

Monday, January 12, 2026

Basseterre, St. Kitts

10:00 PM - 7:00 AM

Tuesday, January 13, 2026

Little Bay, Caribbean

6:00 PM - 8:00 AM

Wednesday, January 14, 2026

Gustavia, St. Barts

11:00 PM - 8:00 AM

Thursday, January 15, 2026

Deshaies, Guadeloupe

10:00 PM - 12:30 PM

Friday, January 16, 2026

Roseau, Dominica

5:00 PM - 8:00 AM

Saturday, January 17, 2026

Pigeon Island, St. Lucia

4:00 PM - 7:00 AM

Sunday, January 18, 2026

Bridgetown, Barbados

6:00 PM - 5:00 AM

Monday, January 19, 2026

Anse Mitan, Martinique

11:00 PM - 9:00 AM

Tuesday, January 20, 2026

Castries, St. Lucia

4:00 PM - 8:00 AM

Tuesday, January 20, 2026

Pigeon Island, St. Lucia

11:59 PM - 6:00 PM

Wednesday, January 21, 2026

Pigeon Island, St. Lucia

6:00 PM - 12:00 AM

Thursday, January 22, 2026

Bequia, St. Vincent and the Grenadines

10:00 PM - 8:00 AM

Friday, January 23, 2026

Mayreau, The Grenadines, Caribbean

6:00 PM - 8:00 AM

Saturday, January 24, 2026

St. George's, Grenada

2:00 PM - 7:00 AM

Sunday, January 25, 2026

Bridgetown, Barbados

6:00 PM - 6:00 AM

Monday, January 26, 2026

Man O'War Bay, Tobago

5:00 PM - 8:00 AM

Tuesday, January 27, 2026

Mayreau, The Grenadines, Caribbean

6:00 PM - 8:00 AM

Wednesday, January 28, 2026

Soufriere, St. Lucia

4:00 PM - 8:00 AM

Thursday, January 29, 2026

Cruising at sea

Friday, January 30, 2026

Kralendijk, Bonaire

10:00 PM - 1:00 PM

Saturday, January 31, 2026

Willemstad, Curacao

6:00 PM - 8:00 AM

Sunday, February 1, 2026

Oranjestad, Aruba, Caribbean

12:00 AM - 6:00 AM

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.