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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

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

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

7-night Eastern Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. John (U.S.V.I.)
Gustavia
St. John's
Little Bay
+2 more

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

$5,500

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.
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

A scenic view of the iconic Plaza de España in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

23-night Transatlantic Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
St. John's
Santa Cruz de La Palma
Santa Cruz de Tenerife
+8 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 9, 2027

1 Sailing

Mar 9, 2027

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

14-night Transatlantic Cruise From San Juan, Puerto Rico

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

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

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

San Juan
Jost Van Dyke
Basseterre
Gustavia
Fort de France
+5 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

2 Sailings

Dec 11, 2027 - Jan 15, 2028

2 Sailings

Dec 11, 2027 - Jan 15, 2028

Published prices from

$5,100

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

7-night Eastern Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. John (U.S.V.I.)
Basseterre
Castries
St. John's
+2 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

2 Sailings

Dec 21 - Dec 28, 2027

2 Sailings

Dec 21 - Dec 28, 2027

Published prices from

$4,100

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
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.)
St. John's
Fort de France
Basseterre
+3 more

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$5,800

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

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

San Juan
Jost Van Dyke
Gustavia
Basseterre
Fort de France
+5 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 4, 2028

1 Sailing

Jan 4, 2028

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.
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 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 $5,000 Off + up to $600 Onboard Credit*
Silversea logo

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

San Juan
Virgin Gorda
Anguilla
Gustavia
Basseterre
+4 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Feb 10, 2028

1 Sailing

Feb 10, 2028

Published prices from

$4,900

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.
Up to $5,000 Off + up to $600 Onboard Credit*
Silversea logo

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

San Juan
Basseterre
Gustavia
Deshaies
St. John's
+3 more

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2028

1 Sailing

Feb 24, 2028

Published prices from

$4,900

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 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

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

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Silversea logo

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

San Juan
St. John (U.S.V.I.)
St. John's
Anguilla
Basseterre
+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 3, 2029

1 Sailing

Feb 3, 2029

Published prices from

$4,350

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

A stunning view of Santa Cruz de la Palma's black sand beach, with gentle waves from the Atlantic Ocean, a colorful town, and green, volcanic mountains in the background.
Silversea logo

14-night Transatlantic Crossing Featuring the Caribbean & Spain Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
St. John's
Santa Cruz de La Palma
Barcelona

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 20, 2029

1 Sailing

Mar 20, 2029

Published prices from

$4,200

per person*

taxes & fees included

    • Showing results 1 - 24 of 25

*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.