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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.

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Feb 14 - Feb 21, 2026

2 Sailings

Feb 14 - Feb 21, 2026

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector: Seeking The Antilles Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+10 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Gems Of The Leeward Islands Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Ocean Crossings Cruise

Lisbon
St. John's
St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Nov 18, 2025 - Dec 5, 2026

2 Sailings

Nov 18, 2025 - Dec 5, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Antilles Adventure Cruise

St. Maarten (Philipsburg)
Basseterre
Gustavia
St. John's
Iles des Saintes
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Sublime Southern Caribbean Cruise

Bridgetown (Barbados)
Mayreau
Roseau
Anse Mitan
Deshaies
+6 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)
Basseterre
St. John's
Iles des Saintes
Roseau
+3 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+14 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

22-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+9 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+30 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
FREE Champagne, Entertainment, Dining & More*
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise

Lisbon
St. John's
St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+16 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026