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

10-night Caribbean Cruise

Bridgetown (Barbados)

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

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

28-night Mediterranean & Caribbean Cruise

Lisbon

Funchal (Madeira)

Las Palmas (Gran Canaria)

Santa Cruz de Tenerife

Ft. Lauderdale

+9 more

Aboard

Silver Dawn

From

Lisbon, Portugal

1 Sailing

Dec 8, 2025

1 Sailing

Dec 8, 2025

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

7-night South Caribbean Cruise - Bridgetown To Bridgetown

Bridgetown (Barbados)

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.

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

14-night Eastern and Southern Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 2026

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.

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

21-night Caribbean Cruise

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 5 - Feb 2, 2026

2 Sailings

Jan 5 - Feb 2, 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 Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Eastern & Southern Caribbean Cruise

Bridgetown (Barbados)

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

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

Bridgetown (Barbados)

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

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.

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

20-night Transatlantic Cruise

Lisbon

Funchal (Madeira)

Santa Cruz de La Palma

Sao Vicente (Mindelo)

Bridgetown (Barbados)

+7 more

Aboard

Silver Spirit

From

Lisbon, Portugal

1 Sailing

Nov 25, 2025

1 Sailing

Nov 25, 2025

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.

21-night Eastern & Southern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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

16-night Southern & Eastern Caribbean Cruise

Bridgetown (Barbados)

Aboard

Silver Nova

From

Bridgetown, Barbados

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 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 Butler Service, Gourmet Dining & More*+ 1 more offer

10-night Caribbean Cruise

Bridgetown (Barbados)

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

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

7-night Southern Caribbean Cruise

Bridgetown (Barbados)

Trois Isles

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

18-night Caribbean Cruise

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 29, 2028

1 Sailing

Feb 29, 2028

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.

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

TCW EXCLUSIVE

14-night Caribbean Cruise

Ft. Lauderdale

Grand Turk

St. Thomas (Charlotte Amalie)

Basseterre

Roseau

+5 more

Aboard

Silver Dawn

From

Fort Lauderdale, Florida

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

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

7-night Caribbean Cruise

Bridgetown (Barbados)

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

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.

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

8-night Caribbean Cruise

Bridgetown (Barbados)

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

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

11-night Caribbean Cruise

Bridgetown (Barbados)

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

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.

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

14-night Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

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

11-night Southern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 25, 2028

1 Sailing

Jan 25, 2028

Published prices from

$5,800

per person*

taxes & fees included

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

7-night Caribbean Cruise

St. Maarten (Philipsburg)

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

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

8-night Caribbean Cruise

Aboard

Silver Nova

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2026

1 Sailing

Dec 29, 2026

Published prices from

$7,900

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 7, 2027

1 Sailing

Feb 7, 2027

Published prices from

$9,300

per person*

taxes & fees included