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91 Results

Taxes and fees included in all prices shown

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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

25-night Canada & Caribbean Cruise From Montreal, Quebec

Montreal
Quebec City
Charlottetown
Halifax (Nova Scotia)
Boston
+11 more

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

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

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+3 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
St. John's
+4 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$6,500

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

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+2 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$5,700

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

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 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

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

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Basseterre
Gustavia
+3 more

Aboard

Silver Ray

From

Miami, Florida

4 Sailings

Dec 11, 2026 - Jan 27, 2027

4 Sailings

Dec 11, 2026 - Jan 27, 2027

Published prices from

$8,350

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

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Fort de France
Roseau
St. John's
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

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

$5,050

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 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

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

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

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

Miami
Grand Turk
Basseterre
Oranjestad
Kralendijk
+4 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$11,050

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

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 wide-angle view of a serene rainforest stream with moss-covered rocks and lush green vegetation near Macapa, Brazil, at the mouth of the Amazon River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

76-night Grand Voyage From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+32 more

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

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

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

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+5 more

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

Published prices from

$7,600

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 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

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

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

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

12-night Southern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Oranjestad
Willemstad
+5 more

Aboard

Silver Spirit

From

Miami, Florida

2 Sailings

Feb 6 - Mar 19, 2027

2 Sailings

Feb 6 - Mar 19, 2027

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

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

    • Showing results 1 - 24 of 91

*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.