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Five cruise ships in the port with very blue water surrounding them

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12 Results

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The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Fort de France
Roseau
St. John's
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,950

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Canouan Island
Roseau
Anguilla
+3 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 19 - Dec 27, 2026

2 Sailings

Dec 19 - Dec 27, 2026

Published prices from

$5,050

per person*

taxes & fees included

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

14-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+7 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

7-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+2 more

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

$4,900

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Castries
St. George's
Canouan Island
+4 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 15 - Feb 18, 2027

2 Sailings

Jan 15 - Feb 18, 2027

Published prices from

$5,900

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
Silversea logo

10-night Eastern & Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Canouan Island
Castries
Trois Isles
Roseau
+6 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Jan 20, 2027

1 Sailing

Jan 20, 2027

Published prices from

$6,500

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
Silversea logo

21-night Eastern & Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Gustavia
Basseterre
Fort de France
+9 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

11-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Gustavia
Roseau
Canouan Island
+5 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 25, 2028

1 Sailing

Jan 25, 2028

Published prices from

$5,200

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.
Silversea logo

10-night Southern Caribbean Featuring St. Kitts & Canouan Cruise From San Juan, Puerto Rico

San Juan
Rodney Bay
Bridgetown (Barbados)
St. George's
Canouan Island
+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Jan 6 - Mar 10, 2029

3 Sailings

Jan 6 - Mar 10, 2029

Published prices from

$5,850

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.
Silversea logo

11-night Southern Caribbean Featuring Aruba & Canouan Cruise From San Juan, Puerto Rico

San Juan
Oranjestad
Willemstad
Kralendijk
Canouan Island
+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Jan 16, 2029

1 Sailing

Jan 16, 2029

Published prices from

$6,450

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.
Silversea logo

17-night Southern Caribbean Featuring Les Saintes & Canouan Juan Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
St. John's
Iles des Saintes
St. Maarten (Philipsburg)
+11 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 10, 2029

1 Sailing

Feb 10, 2029

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.
Silversea logo

11-night Southern Caribbean Featuring Aruba & Canouan Cruise From San Juan, Puerto Rico

San Juan
Gustavia
St. John's
Iles des Saintes
Castries
+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 27, 2029

1 Sailing

Feb 27, 2029

Published prices from

$6,450

per person*

taxes & fees included

*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.