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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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52 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.

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

TCW EXCLUSIVE

10-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

3 Sailings

Dec 2, 2025 - Jan 27, 2026

3 Sailings

Dec 2, 2025 - Jan 27, 2026

Published prices from

$7,900

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Caribbean Cruise

St. Maarten (Philipsburg)

+6 more

Aboard

Silver Spirit

From

Fort Lauderdale, Florida

1 Sailing

Feb 12, 2026

1 Sailing

Feb 12, 2026

Published prices from

$7,100

per person*

taxes & fees included

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

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$6,800

per person*

taxes & fees included

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

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

7-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Jan 3 - Jan 30, 2027

2 Sailings

Jan 3 - Jan 30, 2027

Published prices from

$5,200

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

Published prices from

$9,800

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Miami, Florida

4 Sailings

Dec 11, 2026 - Jan 27, 2027

4 Sailings

Dec 11, 2026 - Jan 27, 2027

Published prices from

$7,300

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$6,800

per person*

taxes & fees included

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

TCW EXCLUSIVE

21-night Caribbean & South America Cruise

Ft. Lauderdale

San Juan

St. Thomas (Charlotte Amalie)

Gustavia

St. John's

+12 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

A high-angle view of the rugged, rocky coastline of St. John, US Virgin Islands, with the deep blue sea crashing against the cliffs and islands in the distance under a cloudy blue sky.

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$6,200

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

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

14-night Eastern and Southern Caribbean Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2026

1 Sailing

Feb 24, 2026

Published prices from

$10,100

per person*

taxes & fees included

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 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

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

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

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise

Ft. Lauderdale

San Juan

St. Thomas (Charlotte Amalie)

Gustavia

St. John's

+7 more

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

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.

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

3 Sailings

Dec 12, 2025 - Feb 6, 2026

3 Sailings

Dec 12, 2025 - Feb 6, 2026

Published prices from

$8,400

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

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

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

28-night Transatlantic Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2026

1 Sailing

Feb 24, 2026

A beautiful mountain lake with a small, snow-covered island in the foreground, with majestic, snow-capped mountains and evergreen trees in the background under a clear blue sky.

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

TCW EXCLUSIVE

76-night Grand Voyage

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

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

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

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

25-night Canada & Caribbean Cruise

Montreal

Quebec City

Charlottetown

Halifax (Nova Scotia)

Boston

+11 more

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026