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4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

Destinations Departure Ports Cruise Lines Deals Land Tours Find Cruises

1-800-377-9383

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72 Results

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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.

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

FREE All-Inclusive Package Upgrade*+ 1 more offer

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

St. Maarten (Philipsburg)

+7 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night San Juan & The Virgin Islands Cruise

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

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Package Upgrade*+ 1 more offer

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

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Feb 14 - Feb 21, 2026

2 Sailings

Feb 14 - Feb 21, 2026

Up to FREE $2,000 Onboard Credit*

7-night Classic Caribbean Yacht Harbors Cruise

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

12 Sailings

Jan 10, 2026 - Mar 13, 2027

12 Sailings

Jan 10, 2026 - Mar 13, 2027

Published prices from

$3,799

per person*

taxes & fees included

FREE All-Inclusive Package Upgrade*+ 1 more offer

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

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 24 - Jan 31, 2026

2 Sailings

Jan 24 - Jan 31, 2026

Immaculate Conception Cathedral in Colon.

FREE All-Inclusive Package Upgrade*+ 1 more offer

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

St. Maarten (Philipsburg)

+13 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

Up to FREE $2,000 Onboard Credit*

14-night Exotic Caribbean Isles Cruise

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

5 Sailings

Jan 10 - Mar 21, 2026

5 Sailings

Jan 10 - Mar 21, 2026

Published prices from

$8,099

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.

FREE All-Inclusive Package Upgrade*+ 1 more offer

18-night Star Collector: Deep Dive Into the Blue: Underwater Worlds of the Caribbean Cruise

Cozumel

Grand Cayman (George Town)

Aboard

Wind Surf

From

Cozumel, Mexico

1 Sailing

Feb 17, 2026

1 Sailing

Feb 17, 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

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027

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 All-Inclusive Package Upgrade*+ 1 more offer

5-night Barefoot Break in the British Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night San Juan & The Virgin Islands Cruise

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

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

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

4 Sailings

Dec 14, 2025 - Mar 28, 2026

4 Sailings

Dec 14, 2025 - Mar 28, 2026

Up to FREE $2,000 Onboard Credit*

14-night Yachtsman's Island Jewels Cruise

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 2026

Published prices from

$8,899

per person*

taxes & fees included

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Lovely Leewards Cruise

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

A close-up aerial view of the dramatic limestone bluff, known as the "Bluff," a landmark on Cayman Brac island, with waves crashing against its vertical face.

FREE All-Inclusive Package Upgrade*+ 1 more offer

19-night Star Collector: Caribbean Cultures: Latin America & the Greater Antilles Cruise

Aboard

Wind Surf

From

Colon, Panama

1 Sailing

Feb 9, 2026

1 Sailing

Feb 9, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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.

Up to FREE $2,000 Onboard Credit*

14-night Gems Of The Caribbean Cruise

St. Maarten (Philipsburg)

Sopers Hole

Carambola Beach

St. Pierre

Port Elizabeth (Bequia)

+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 17 - Feb 21, 2026

2 Sailings

Jan 17 - Feb 21, 2026

Published prices from

$8,699

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

12-night Azure Caribbean Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Jan 5, 2026

1 Sailing

Jan 5, 2026

Published prices from

$3,499

per person*

taxes & fees included

FREE All-Inclusive Package Upgrade*+ 1 more offer

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.

FREE All-Inclusive Package Upgrade*+ 1 more offer

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

19-night Star Collector: Hearty Ports & Rum Punches - A Trans-Atlantic Crossing Cruise

Lisbon

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Feb 7, 2026

2 Sailings

Jan 31 - Feb 7, 2026

Up to FREE $2,000 Onboard Credit*

14-night Southern Island Discovery Cruise

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 2026