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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.
Military Families Save 10%*
MSC Cruises logo

14 nights South Caribbean

Aboard

MSC Virtuosa

From

Bridgetown, Barbados

Published prices from

$1,219

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

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.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Yachtsman's Island Jewels Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Cupecoy Beach with white resort buildings, St. Maarten.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

7-night Yachtsman's Caribbean Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,654

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.
Military Families Save 10%*
MSC Cruises logo

14 nights Central Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

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.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

7-night Southern Caribbean with Barbados Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

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*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Dutch Isles Delights Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$6,349

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*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

28-night Antilles & Atlantic Gems Voyage

Aboard

Allura

From

Miami, Florida

Published prices from

$10,549

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
MSC Cruises logo

14 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$8,278

per person*

taxes & fees included

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Military Families Save 10%*
MSC Cruises logo

7 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$531

per person*

taxes & fees included

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Military Families Save 10%*
MSC Cruises logo

7 nights South Caribbean

Aboard

MSC Virtuosa

From

Pointe-à-Pitre, Guadeloupe

Published prices from

$852

per person*

taxes & fees included

A view of the stunning architecture of the Hassan II Mosque in Casablanca, Morocco, featuring a long series of ornate stone arches and a spacious courtyard.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

27-night Caribbean & Atlantic Passage Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Rocky beach and palm trees in Barbados.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

14-night Exotic Caribbean Isles Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$7,649

per person*

taxes & fees included

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

10-night Gems Of The Leeward Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,757

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$12,244

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
Save up to 30% on Last Minute Sailings*+ 1 more offer
Seabourn logo

20-night Spice Islands & Spice Market Crossing Cruise

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

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.
Military Families Save 10%*
MSC Cruises logo

23 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$1,399

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.
Military Families Save 10%*
MSC Cruises logo

20 nights South Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$1,139

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.
MSC Cruises logo

6 nights South Caribbean

Aboard

MSC Virtuosa

From

Pointe-à-Pitre, Guadeloupe

Published prices from

$479

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.
Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers
Princess Cruises logo

18-night Southern Caribbean Adventurer Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

Speicherstadt Warehouse District in Hamburg.
Military Families Save 10%*
MSC Cruises logo

20 nights South Caribbean

Aboard

MSC Virtuosa

From

Bridgetown, Barbados

Published prices from

$1,489

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
TCW EXCLUSIVE
Regent Seven Seas Cruises.

16-night Spotlight With Southern Living Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

Published prices from

$11,849

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.