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*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.

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Windward Ways & Tobago Cays Cruise

Bridgetown (Barbados)
Man O'War Bay
Mayreau
Soufriere
Kralendijk
+3 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Windward Islands & Spanish New World Cruise

Bridgetown (Barbados)
Man O'War Bay
Mayreau
Soufriere
Kralendijk
+7 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)
Anse Mitan
Castries
Pigeon Island
Bequia
+8 more

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

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.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Windward Ways and Tobago Cays Cruise

Oranjestad
Willemstad
Kralendijk
Soufriere
Mayreau
+3 more

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 15, 2026

1 Sailing

Mar 15, 2026

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.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

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

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+19 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+33 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026