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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.

14-night Caribbean Cruise From San Juan, Puerto Rico

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.

7-night Caribbean Cruise From San Juan, Puerto Rico

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

$5,300

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.

8-night Caribbean Cruise From San Juan, Puerto Rico

St. John (U.S.V.I.)

Aboard

Silver Nova

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2026

1 Sailing

Dec 29, 2026

Published prices from

$8,000

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.

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

St. John (U.S.V.I.)

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

$5,100

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 & Southern Caribbean Cruise From San Juan, Puerto Rico

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

$7,000

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.

23-night Transatlantic Cruise From San Juan, Puerto Rico

Santa Cruz de La Palma

Santa Cruz de Tenerife

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.

14-night Transatlantic Cruise From San Juan, Puerto Rico

Santa Cruz de La Palma

Santa Cruz de Tenerife

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 9, 2027

1 Sailing

Mar 9, 2027

Published prices from

$8,000

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.

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

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

$6,100

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.

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

St. John (U.S.V.I.)

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

$5,400

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.

8-night Caribbean Cruise From San Juan, Puerto Rico

St. John (U.S.V.I.)

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$8,400

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.

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

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

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.

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

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.

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

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 25, 2028

1 Sailing

Jan 25, 2028

Published prices from

$6,500

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.