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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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41 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.

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

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

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

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

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

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

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

TCW EXCLUSIVE

14-night Eastern & Southern Caribbean Cruise

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$11,300

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

TCW EXCLUSIVE

10-night Caribbean Cruise

Miami

St. John (U.S.V.I.)

St. Maarten (Philipsburg)

Basseterre

Iles des Saintes

+5 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$6,400

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

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 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

Bridgetown (Barbados)

Castries

St. George's

St. Maarten (Philipsburg)

Basseterre

+7 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 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

28-night Transatlantic Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2026

1 Sailing

Feb 24, 2026

A tropical beach with golden sand, swaying palm trees, and two sailboats anchored in the bay in front of the lush green mountains of Soufrière, St. Lucia.

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

8-night Caribbean Cruise

Bridgetown (Barbados)

Aboard

Silver Nova

From

Bridgetown, Barbados

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$7,100

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

14-night Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

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

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

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

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

TCW EXCLUSIVE

14-night Eastern & Southern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

1 Sailing

Dec 23, 2025

1 Sailing

Dec 23, 2025

Published prices from

$12,700

per person*

taxes & fees included

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 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 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

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

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

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

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

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