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Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 8, 2025

1 Sailing

Dec 8, 2025

Published prices from

$5,800

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

7-night Eastern and Southern Caribbean Cruise

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

+2 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 2026

Published prices from

$5,800

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

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

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

10-night Caribbean Cruise

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

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

TCW EXCLUSIVE

10-night Caribbean Cruise

Aboard

Silver Spirit

From

Fort Lauderdale, Florida

1 Sailing

Jan 16, 2026

1 Sailing

Jan 16, 2026

Published prices from

$7,300

per person*

taxes & fees included

8-night Caribbean Cruise

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Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$6,000

per person*

taxes & fees included

10-night Southern Caribbean Cruise

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Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 15 - Feb 18, 2027

2 Sailings

Jan 15 - Feb 18, 2027

Published prices from

$6,700

per person*

taxes & fees included

7-night Eastern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

3 Sailings

Dec 21, 2027 - Feb 5, 2028

3 Sailings

Dec 21, 2027 - Feb 5, 2028

Published prices from

$4,600

per person*

taxes & fees included

14-night Eastern and Southern Caribbean Cruise

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

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 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.

11-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 5, 2026 - Feb 29, 2028

3 Sailings

Jan 5, 2026 - Feb 29, 2028

Published prices from

$5,600

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.

10-night Eastern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

4 Sailings

Dec 11, 2027 - Feb 22, 2028

4 Sailings

Dec 11, 2027 - Feb 22, 2028

Published prices from

$5,000

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.

10-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 2, 2026

1 Sailing

Feb 2, 2026

Published prices from

$7,200

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.

8-night Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 19 - Dec 27, 2026

2 Sailings

Dec 19 - Dec 27, 2026

Published prices from

$6,400

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.

14-night Caribbean Cruise

St. George's

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

Basseterre

+7 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

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

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.

7-night Eastern & Southern Caribbean Cruise

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

+2 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 4 - Jan 18, 2026

2 Sailings

Jan 4 - Jan 18, 2026

Published prices from

$6,100

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.

TCW EXCLUSIVE

12-night Southern Caribbean Cruise

Aboard

Silver Spirit

From

Miami, Florida

2 Sailings

Feb 6 - Mar 19, 2027

2 Sailings

Feb 6 - Mar 19, 2027

Published prices from

$7,000

per person*

taxes & fees included

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

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

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

7-night Eastern & Southern Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 15, 2025

1 Sailing

Dec 15, 2025

Published prices from

$5,200

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.

21-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 5 - Feb 2, 2026

2 Sailings

Jan 5 - Feb 2, 2026

7-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

5 Sailings

Dec 22, 2025 - Mar 11, 2028

5 Sailings

Dec 22, 2025 - Mar 11, 2028

Published prices from

$3,800

per person*

taxes & fees included

20-night Transatlantic Cruise

Lisbon

Funchal (Madeira)

Santa Cruz de La Palma

Sao Vicente (Mindelo)

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

+7 more

Aboard

Silver Spirit

From

Lisbon, Portugal

1 Sailing

Nov 25, 2025

1 Sailing

Nov 25, 2025

10-night Southern Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$4,400

per person*

taxes & fees included

A white colonial-style cathedral with a bell tower and wooden doors is visible under a clear blue sky, likely in Santa Marta, Colombia.

9-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

3 Sailings

Dec 1, 2025 - Feb 3, 2026

3 Sailings

Dec 1, 2025 - Feb 3, 2026

Published prices from

$5,300

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

10-night Eastern & Southern Caribbean Cruise