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8 Results

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

8-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. John (U.S.V.I.)
Charlestown
Roseau
St. John's
+3 more

Aboard

Silver Nova

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2026

1 Sailing

Dec 29, 2026

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

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
St. George's
Bequia
Fort de France
+4 more

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$5,200

per person*

taxes & fees included

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 breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.
Silversea logo

11-night Eastern Caribbean Featuring Puerto Rico & St. Barts Cruise From Miami, Florida

Miami
Grand Turk
St. John (U.S.V.I.)
Gustavia
Anguilla
+3 more

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Dec 22, 2028

1 Sailing

Dec 22, 2028

Published prices from

$5,750

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 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

*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.