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13 Results

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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

10-night Caribbean Cruise From Miami, Florida

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

$5,200

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

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

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

San Juan
Jost Van Dyke
Gustavia
St. John's
Little Bay
+6 more

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

$5,300

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

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Castries
Trois Isles
+6 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$6,800

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

18-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Willemstad
Oranjestad
+10 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 29, 2028

1 Sailing

Feb 29, 2028

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

16-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan
Charlestown
St. Maarten (Philipsburg)
Iles des Saintes
Roseau
+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2028

1 Sailing

Dec 7, 2028

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
Silversea logo

9-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan
Charlestown
St. Maarten (Philipsburg)
Iles des Saintes
Roseau
+4 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2028

1 Sailing

Dec 7, 2028

Published prices from

$5,300

per person*

taxes & fees included

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

7-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
Iles des Saintes
St. Maarten (Philipsburg)
+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

5 Sailings

Dec 16, 2028 - Feb 10, 2029

5 Sailings

Dec 16, 2028 - Feb 10, 2029

Published prices from

$4,150

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Silversea logo

14-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan
St. John (U.S.V.I.)
St. John's
Charlestown
St. Maarten (Philipsburg)
+6 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Dec 23, 2028 - Jan 27, 2029

2 Sailings

Dec 23, 2028 - Jan 27, 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
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.