55 Results

Sort

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

25-night Canada & Caribbean Cruise

Aboard

Silver Shadow

From

Montreal, Quebec

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.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,257

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

11-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

Miami, Florida

Published prices from

$5,500

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 All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,593

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,381

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

Aboard

Silver Shadow

From

Miami, Florida

Published prices from

$5,900

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

15-night Southern Caribbean In Depth Cruise

Aboard

Seabourn Ovation

From

Miami, Florida

Published prices from

$7,799

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
Seabourn logo

8-night Southern Caribbean Gems Cruise

Aboard

Seabourn Ovation

From

Miami, Florida

Published prices from

$4,099

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
Seabourn logo

14-night Leeward Island Jewels Cruise

Aboard

Seabourn Quest

From

Miami, Florida

Published prices from

$5,999

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 $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*
Seabourn logo

14-night Exotic Caribbean In Depth Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$8,399

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*
Seabourn logo

7-night Classic Caribbean Yacht Harbors Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$4,499

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

Aboard

Silver Shadow

From

Miami, Florida

Published prices from

$5,000

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.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise

Aboard

Wind Surf

From

Lisbon, Portugal

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Caribbean Cruise

Aboard

Silver Shadow

From

Miami, Florida

Published prices from

$4,300

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 All-Inclusive Upgrade*+ 1 more offer
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,167

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.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$5,419

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
Seabourn logo

16-night Leeward Island Holiday Cruise

Aboard

Seabourn Quest

From

Miami, Florida

Published prices from

$10,999

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

Published prices from

$3,500

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

14-night Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

16-night Southern & Eastern Caribbean Cruise

Aboard

Silver Nova

From

Bridgetown, Barbados

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

8-night Caribbean Cruise

Aboard

Silver Nova

From

San Juan, Puerto Rico

Published prices from

$5,100

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Eastern Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

Published prices from

$3,900

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.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

10-night Eastern & Southern Caribbean Cruise

Aboard

Silver Shadow

From

San Juan, Puerto Rico

Published prices from

$5,500

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 $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*
Seabourn logo

14-night Caribbean Gems In Depth Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$8,899

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

10-night Caribbean Cruise

Aboard

Silver Shadow

From

Bridgetown, Barbados

Published prices from

$6,000

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.