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Sunshine Skyway Bridge near Tampa, Florida at sunset.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

15-night Leeward Isles Serenade Voyage

Aboard

Insignia

From

Tampa, Florida

Published prices from

$4,160

per person*

taxes & fees included

A beautiful sailboat rests in the shallow, clear turquoise waters off the coast of Belize City, with lush palm trees and colorful buildings lining the shore.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Cunard

21-night Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$2,259

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 South Caribbean

Aboard

MSC Virtuosa

From

Bridgetown, Barbados

Published prices from

$1,219

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Ultimate Southern Caribbean Cruise

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

Published prices from

$1,562

per person*

taxes & fees included

A scenic view of Princess Cays, Bahamas, featuring a row of colorful cabanas with thatched roofs, surrounded by swaying palm trees on a white-sand beach.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

20-night Caribbean Explorer Cruise

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Eastern Caribbean With Tortola Cruise

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

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

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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

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

7 nights Central Caribbean

Aboard

MSC Virtuosa

From

Fort de France, Martinique

Published prices from

$737

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.
Military Families Save 10%*
MSC Cruises logo

7 nights Central Caribbean

Aboard

MSC Virtuosa

From

Pointe-à-Pitre, Guadeloupe

Published prices from

$808

per person*

taxes & fees included

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Barbados, Antigua & St. Lucia

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

Published prices from

$749

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.
FREE Dining, Onboard Activities & More*+ 2 more offers
Royal Caribbean logo

7-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

Published prices from

$1,154

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Wi-Fi, Dining, Spa Access & More*+ 1 more offer
Viking

10-night West Indies Explorer Cruise

Aboard

Viking Sea

From

San Juan, Puerto Rico

Published prices from

$3,699

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
Cunard

12-night Eastern Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

Published prices from

$1,399

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

8-night Antigua, St. Kitts, & San Juan Cruise

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

Published prices from

$2,213

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
Holland America logo

11-night Eastern Caribbean: Windward & Leeward Islands Cruise

Aboard

Zuiderdam

From

Miami, Florida

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

21-night Eastern & Southern Caribbean: Leeward & Abc Islands Cruise

Aboard

Zuiderdam

From

Miami, Florida

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

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Southern Caribbean With Martinique Cruise

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

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

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

7-night Classic Caribbean Yacht Harbors Cruise

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

Published prices from

$3,824

per person*

taxes & fees included

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

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

12-night Caribbean Islander Cruise

Aboard

Regal Princess

From

Galveston, Texas

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

*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.