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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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29 Results

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Showing results 1 - 24 of 29

*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.

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

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 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

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

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

14-night Transatlantic Cruise

San Juan

Jost Van Dyke

St. John's

Santa Cruz de La Palma

Santa Cruz de Tenerife

+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 9, 2027

1 Sailing

Mar 9, 2027

Published prices from

$7,600

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

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

Modern building illuminated at sunset along the coast in Callao, Peru.

Up to $500 FREE Onboard Credit*

TCW EXCLUSIVE

77-night Grand Voyage Cruise

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

Up to $500 FREE Onboard Credit*

TCW EXCLUSIVE

12-night Caribbean Cruise

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Jan 3, 2028

1 Sailing

Jan 3, 2028

Published prices from

$7,400

per person*

taxes & fees included

8-night Caribbean Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$6,600

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

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

7-night Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Dec 20, 2026 - Feb 26, 2027

3 Sailings

Dec 20, 2026 - Feb 26, 2027

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

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

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.

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

TCW EXCLUSIVE

10-night 2028 World Cruise Segment: Chapter 1 - Anthem of the Tropics

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

Published prices from

$5,900

per person*

taxes & fees included

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

TCW EXCLUSIVE

41-night 2028 World Cruise Segment: Chapter 1, 2 & 3

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

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

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

21-night Eastern & Southern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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

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

11-night Eastern & Southern Caribbean Cruise

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 4, 2028

1 Sailing

Jan 4, 2028

Published prices from

$6,500

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

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 panoramic shot of the Gqeberha coastline in South Africa, showcasing the city skyline and a pier over the water, with waves crashing on the rocky shoreline in the foreground.

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

TCW EXCLUSIVE

132-night 2028 World Cruise: An Ode to the Moment

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

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