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57 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

Published prices from

$17,100

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 $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

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

15-night Southern Caribbean In Depth Cruise From Miami, Florida

Miami
San Juan
Jost Van Dyke
Carambola Beach
Roseau
+8 more

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$8,199

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Leeward Island Jewels Cruise From Miami, Florida

Miami
San Juan
Road Bay
Carambola Beach
Roseau
+6 more

Aboard

Seabourn Quest

From

Miami, Florida

2 Sailings

Nov 22 - Dec 6, 2026

2 Sailings

Nov 22 - Dec 6, 2026

Published prices from

$6,999

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*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Exotic Caribbean In Depth Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

7 Sailings

Nov 28, 2026 - Mar 13, 2027

7 Sailings

Nov 28, 2026 - Mar 13, 2027

Published prices from

$7,999

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*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Classic Caribbean Yacht Harbors Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+3 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

13 Sailings

Nov 28, 2026 - Mar 11, 2028

13 Sailings

Nov 28, 2026 - Mar 11, 2028

Published prices from

$4,099

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

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

16-night Leeward Island Holiday Cruise From Miami, Florida

Miami
San Juan
Road Bay
Carambola Beach
Marigot
+8 more

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,999

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

$4,600

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

15-night An Extended Journey Through Island Joys & Volcanic Majesty From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
Cruz Bay
San Juan
+8 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Published prices from

$9,835

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

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 a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

16-night An Extended Journey Of Dazzling Skylines & Wildlife Exploration From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
St. John's
Little Bay
Roadtown
+6 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Jan 4, 2027

1 Sailing

Jan 4, 2027

Published prices from

$8,365

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

7-night A Journey Of Caribbean Delicacies & Idyllic Islands From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
St. John's
Little Bay
Roadtown
+2 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Jan 4, 2027

1 Sailing

Jan 4, 2027

Published prices from

$4,270

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 captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Gems In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Jan 16 - Mar 6, 2027

3 Sailings

Jan 16 - Mar 6, 2027

Published prices from

$10,199

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

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey From Vibrant Shores To Spectacular Scenery From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
Roadtown
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Mar 29, 2027

1 Sailing

Mar 29, 2027

Published prices from

$9,940

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

17-night A Grand Journey Through Balmy Shores & Enchanting Nature To Panama’S Wonders From San Juan, Puerto Rico

San Juan
Gustavia
Little Bay
Basseterre
Key West
+9 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2027

1 Sailing

Apr 5, 2027

Published prices from

$12,775

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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Balmy Shores & Stirring Scenery From San Juan, Puerto Rico

San Juan
Gustavia
Little Bay
Basseterre
Key West
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2027

1 Sailing

Apr 5, 2027

Published prices from

$5,250

per person*

taxes & fees included

A rugged, high-angle shot of the dramatic rocky coastline of Hebron, Labrador, with waves crashing against the jagged cliffs and dark blue water stretching to the horizon.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

69-night Northern Hemisphere Explorer: Arctic To South America Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+38 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

"A beautiful aerial view of the colorful, snow-covered houses of the small village of Uummannaq, Northwest Greenland, at the foot of the magnificent Uummannaq Mountain. "
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

53-night Arctic Expeditions & Southern Caribbean Harbors Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+29 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

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

94-night Grand Expedition: Pole To Pole Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Pond Inlet
Northwest Passage
Ellesmere Island
+45 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Aug 17, 2027

1 Sailing

Aug 17, 2027

Colorful houses along the waterfront in Nuuk, Greenland.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

82-night Grand Expedition: Arctic To Antarctica Cruise From Reykjavik, Iceland

Reykjavik
Kangerlussuaq Fjord
Nuuk
Iqaluit (Nunavut)
Diana Island
+42 more

Aboard

Seabourn Venture

From

Reykjavik, Iceland

2 Sailings

Aug 29, 2027 - Aug 30, 2028

2 Sailings

Aug 29, 2027 - Aug 30, 2028

    • Showing results 1 - 24 of 57

*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.