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21-night Caribbean & South America Cruise

Ft. Lauderdale

San Juan

Gustavia

+12 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Cupecoy Beach with white resort buildings, St. Maarten.

19-night Yachtsman's Caribbean & Atlantic Passage Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 20, 2027

1 Sailing

Mar 20, 2027

Published prices from

$9,699

per person*

taxes & fees included

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

28-night Mediterranean Medley & Atlantic Crossing Cruise

Aboard

Seabourn Ovation

From

Piraeus (Athens), Greece

1 Sailing

Oct 30, 2027

1 Sailing

Oct 30, 2027

Published prices from

$14,099

per person*

taxes & fees included

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

10-night Caribbean Cruise

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$6,300

per person*

taxes & fees included

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

2 Sailings

Dec 19, 2025 - Feb 3, 2026

2 Sailings

Dec 19, 2025 - Feb 3, 2026

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

14-night Eastern and Southern Caribbean Cruise

Up to $500 FREE Onboard Credit*+ 1 more offer

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 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 Butler Service, Gourmet Dining & More*+ 1 more offer

21-night Atlantic Crossing & Iberian Peninsula Cruise

Aboard

Seabourn Ovation

From

Barcelona, Spain

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$9,599

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.

14-night Caribbean Cruise

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 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.

10-night Eastern & Southern Caribbean Cruise

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Jan 20, 2027

1 Sailing

Jan 20, 2027

Published prices from

$6,800

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.

12-night Treasures Of Aruba, Bonaire & Curacao Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$15,999

per person*

taxes & fees included

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.

14-night Caribbean Gems In Depth Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Jan 16 - Mar 6, 2027

3 Sailings

Jan 16 - Mar 6, 2027

Published prices from

$8,399

per person*

taxes & fees included

A long, green steel-arched bridge with multiple supports, the Laviolette Bridge, spanning the wide St. Lawrence River near Trois-Rivières, with a grassy riverbank in the foreground.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

13-night Atlantic Crossing Cruise

Aboard

Seabourn Ovation

From

Lisbon, Portugal

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$5,299

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

7-night Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 11 - Feb 26, 2026

2 Sailings

Jan 11 - Feb 26, 2026

Published prices from

$5,500

per person*

taxes & fees included

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.

14-night Exotic Caribbean In Depth Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

7 Sailings

Nov 28, 2026 - Mar 13, 2027

7 Sailings

Nov 28, 2026 - Mar 13, 2027

Published prices from

$7,299

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

14-night Yachtsman's Island Jewels Cruise

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

14-night Yachtsman's Caribbean In Depth Cruise

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$7,999

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.

10-night Eastern & Southern Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Jan 10 - Feb 6, 2027

2 Sailings

Jan 10 - Feb 6, 2027

Published prices from

$6,300

per person*

taxes & fees included

A scenic Caribbean bay near Kingstown, Saint Vincent and the Grenadines, with small boats anchored in the turquoise water and lush green hillsides with colorful houses.

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

12-night Eastern & Southern Caribbean Cruise

Ft. Lauderdale

San Juan

Gustavia

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$7,800

per person*

taxes & fees included

7-night Southern Caribbean Cruise

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

St. Vincent (Kingstown)

Roseau

Gustavia

+3 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 12, 2026

1 Sailing

Feb 12, 2026

Published prices from

$5,400

per person*

taxes & fees included

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.

26-night Crossing And Southern Caribbean Cruise

Aboard

Seabourn Ovation

From

Barcelona, Spain

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

14-night Yachtsman's Island Jewels Cruise

St. Pierre

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Mar 7, 2026

2 Sailings

Jan 31 - Mar 7, 2026

Published prices from

$8,899

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

20-night Southern Caribbean Discovery Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$11,499

per person*

taxes & fees included

7-night Caribbean Cruise

St. Vincent (Kingstown)

St. George's

+3 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Published prices from

$5,600

per person*

taxes & fees included

7-night Caribbean Gems Cruise