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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

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

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

$4,898

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

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$12,000

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

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

$12,700

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

14-night An Extended Journey Of Blissful Escapes & Shoreline Splendour From Miami, Florida

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

Published prices from

$10,910

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*+ 2 more offers

7-night A Journey Through Beguiling Caribbean Coastlines & Lush Landscapes From Miami, Florida

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

Published prices from

$4,480

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*+ 2 more offers

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

$3,902

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

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

$2,443

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

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.

Up to $500 FREE Onboard Credit*+ 3 more offers

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

$6,799

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*+ 3 more offers

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

$3,654

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

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

$5,524

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

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

$6,884

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

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

$3,824

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

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

$7,700

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

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

$9,500

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.

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

15-night An Extended Journey Through Wild Beauty And Tropical Festivities From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$10,985

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

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

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$5,132

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 2 more offers

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

$2,693

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

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

$9,349

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.

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

16-night An Extended Journey Of Sparkling Skies & Dramatic Natural Beauty From Miami, Florida

Catalina Island/Casa de Campo

St. Maarten (Philipsburg)

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$15,975

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

8-night A Journey Of Tropical Festivities & Dazzling Island Beauty From Miami, Florida

Catalina Island/Casa de Campo

St. Maarten (Philipsburg)

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$5,285

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

15-night An Extended Journey Into Island Bliss & Lively Celebrations From San Juan, Puerto Rico

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$12,365

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

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

*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.