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20 Results

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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

7-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Fort de France
Deshaies
Gustavia
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 5, 2026 - Feb 28, 2027

2 Sailings

Dec 5, 2026 - Feb 28, 2027

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

$4,500

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 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

8-night Caribbean Cruise From Bridgetown, Barbados

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

Aboard

Silver Nova

From

Bridgetown, Barbados

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$4,700

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

11-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Deshaies
St. John's
Oranjestad
+5 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 4, 2027 - Feb 29, 2028

3 Sailings

Jan 4, 2027 - Feb 29, 2028

Published prices from

$5,100

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

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

12-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+5 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 25 - Mar 7, 2027

2 Sailings

Jan 25 - Mar 7, 2027

Published prices from

$6,100

per person*

taxes & fees included

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

12-night Eastern & Southern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Basseterre
Gustavia
+7 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 7, 2027

1 Sailing

Feb 7, 2027

Published prices from

$8,300

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 panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

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

Bridgetown (Barbados)
Bequia
St. George's
Fort de France
Deshaies
+7 more

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Feb 26, 2027

1 Sailing

Feb 26, 2027

Published prices from

$8,100

per person*

taxes & fees included

A breathtaking panoramic aerial view of the city of Mindelo on the island of São Vicente, Cape Verde, with its bustling harbor and town surrounded by rugged, volcanic hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

25-night Trans-Atlantic Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Willemstad
+9 more

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Mar 19, 2027

1 Sailing

Mar 19, 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 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

$5,300

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

13-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Bequia
Castries
Kralendijk
+7 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

Published prices from

$7,500

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

12-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Castries
Kralendijk
Willemstad
+6 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 10 - Feb 17, 2028

3 Sailings

Jan 10 - Feb 17, 2028

Published prices from

$5,600

per person*

taxes & fees included

An aerial shot of the port city of Ushuaia, Argentina, at dusk, showing city lights along the Beagle Channel with the snow-capped Andes Mountains in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

77-night Grand Voyage Cruise From Miami, Florida

Miami
Cozumel
Puerto Limon
Colon (Panama)
Panama Canal
+37 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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

7-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Fort de France
Gustavia
Roseau
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 22 - Mar 11, 2028

3 Sailings

Jan 22 - Mar 11, 2028

Published prices from

$4,100

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

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

26-night Transatlantic Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Castries
Fort de France
Roseau
+10 more

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

12-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Castries
Fort de France
Roseau
+7 more

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

Published prices from

$7,450

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.