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Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Dining, Onboard Activities & More*+ 1 more offer
Royal Caribbean logo

10-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

Published prices from

$1,420

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

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

7-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Bridgetown, Barbados

Published prices from

$7,200

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

14-night Eastern and Southern Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

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

7-night Caribbean Cruise

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$6,300

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

12-night Dutch Isles Delights Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$5,199

per person*

taxes & fees included

Two colorful striped beach chairs sit on the white sand beach of Great Stirrup Cay, Bahamas, facing the clear turquoise water under a bright blue sky with palm fronds overhead.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

28-night Antilles & Atlantic Gems Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$12,649

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
FREE Dining, Waterparks, Entertainment & More*+ 1 more offer
Carnival Cruise Line

14-night Journeys - Southern Caribbean Cruise

Aboard

Carnival Venezia

From

Port Canaveral, Florida

Published prices from

$1,844

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.
Up to 60% off 2nd Guest + Kids Sail Free*
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

Published prices from

$612

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.
Active & Retired Military Members Save up to $200*+ 1 more offer
Celebrity Cruise Line logo

11-night Southern Caribbean Intensive Cruise

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

Published prices from

$1,583

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
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Best Of Southern Caribbean Cruise

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

Published prices from

$1,894

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*+ 1 more offer
TCW EXCLUSIVE
Oceania Cruises

12-night Exotic Caribbean Escape Voyage

Aboard

Marina

From

Miami, Florida

Published prices from

$3,799

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

7-night Colon To San Juan Cruise

Aboard

Grandeur of the Seas

From

Colon, Panama

Published prices from

$718

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.
Celebrity Cruise Line logo

9-night Southern Caribbean Cruise

Aboard

Celebrity Summit

From

San Juan, Puerto Rico

Published prices from

$1,177

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night Heavenly Hideaways Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

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

14-night Festive Caribbean Frolic Voyage

Aboard

Sirena

From

Miami, Florida

Published prices from

$4,399

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Celebrity Cruise Line logo

13-night Ultimate Southern Caribbean Holiday Cruise

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

Published prices from

$2,946

per person*

taxes & fees included

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

26-night Transatlantic Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$5,259

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to 60% off 2nd Guest + Kids Sail Free*
Royal Caribbean logo

8-night Southern Caribbean Holiday Cruise

Aboard

Rhapsody of the Seas

From

San Juan, Puerto Rico

Published prices from

$1,348

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Give $250, Get $250*
Regent Seven Seas Cruises.

10-night Untouched Treasures Cruise

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

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.
Give $250, Get $250*
Regent Seven Seas Cruises.

10-night Tropical Heart & Soul Cruise

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

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.
Give $250, Get $250*
Regent Seven Seas Cruises.

10-night Be My Island Valentine Cruise

Aboard

Seven Seas Grandeur

From

Bridgetown, Barbados

*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.