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12 Results

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Offramp
Immaculate Conception Cathedral in Colon.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+13 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+7 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night San Juan & The Virgin Islands Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 23 - Mar 6, 2026

4 Sailings

Jan 23 - Mar 6, 2026

*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.

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

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

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern Caribbean: Antilles & Private Island Holiday Cruise

Ft. Lauderdale
Cruz Bay
Port of Spain
St. George's
Roseau
+6 more

Aboard

Volendam

From

Fort Lauderdale, Florida

1 Sailing

Dec 21, 2025

1 Sailing

Dec 21, 2025

Published prices from

$2,274

per person*

taxes & fees included

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 Champagne, Entertainment, Dining & More*
Windstar

11-night Gems Of The Leeward Islands Cruise

San Juan
Cruz Bay
Gustavia
Basseterre
Falmouth Harbour
+6 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 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

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night San Juan & The Virgin Islands Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

10 Sailings

Nov 2, 2025 - Jan 10, 2027

10 Sailings

Nov 2, 2025 - Jan 10, 2027

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 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

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

7 Sailings

Jan 23 - Mar 6, 2026

7 Sailings

Jan 23 - Mar 6, 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