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Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

25-night Canada & Caribbean Cruise From Montreal, Quebec

Halifax (Nova Scotia)

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

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.

Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,568

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$7,400

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.

Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,070

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

8 Sailings

Nov 15, 2026 - Mar 20, 2028

8 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,548

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$8,000

per person*

taxes & fees included

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.

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

Carambola Beach

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$7,198

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

8-night Southern Caribbean Gems Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$3,998

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

14-night Leeward Island Jewels Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

2 Sailings

Nov 22 - Dec 6, 2026

2 Sailings

Nov 22 - Dec 6, 2026

Published prices from

$6,498

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.

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

Bridgetown (Barbados)

Carambola Beach

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

$6,998

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 Classic Caribbean Yacht Harbors Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Carambola Beach

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

$3,598

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$7,500

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.

Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 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.

10-night Caribbean Cruise From Miami, Florida

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

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$6,300

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,623

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.

Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

14 Sailings

Dec 19, 2026 - Jan 23, 2028

14 Sailings

Dec 19, 2026 - Jan 23, 2028

Published prices from

$4,208

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.

16-night Leeward Island Holiday Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,998

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.

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 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.

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

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

$7,898

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.

10-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$10,800

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

*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.