87 Results

Sort

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

16-night Spotlight With Southern Living Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

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

$2,862

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 beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Caribbean Voyage: San Juan, Antigua & Barbados

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$3,949

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*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

12-night Antillean Island Sojourn Voyage

Aboard

Vista

From

Miami, Florida

Published prices from

$4,462

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Maarten

Aboard

Azamara Journey

From

Bridgetown, Barbados

Published prices from

$4,499

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
Regent Seven Seas Cruises.

10-night Riviera Chic & Caribbean Cool Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

Published prices from

$7,499

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

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

10-night Tropical Island Havens Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$3,899

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

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Southern Caribbean Cruise

Aboard

Silver Spirit

From

Bridgetown, Barbados

Published prices from

$4,300

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

12-night Collector's Caribbean Voyage

Aboard

Marina

From

Miami, Florida

Published prices from

$4,099

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

17-night Tropical Sparkle & Holiday Cheer Cruise

Aboard

Seven Seas Splendor

From

Galveston, Texas

Published prices from

$9,999

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 Ray

From

Miami, Florida

Published prices from

$6,400

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*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

9-night Sunlit Caribbean Gems Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$3,549

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas

Aboard

Azamara Journey

From

Bridgetown, Barbados

Published prices from

$4,949

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

18-night Caribbean Holiday Voyage: San Juan, St. Barts & Curacao

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$6,249

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

10-night Southern Caribbean Voyage: Antigua, St.Barts & Martinique

Aboard

Azamara Journey

From

San Juan, Puerto Rico

Published prices from

$2,549

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

$5,519

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

17-night Tropical Serenade Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$9,499

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.