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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.
Celebrity Cruise Line logo

7-nights Tortola, St. Kitts & Puerto Plata Cruise From Miami, Florida

Aboard

Celebrity Beyond

From

Miami, Florida

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Royal Caribbean logo

8-night Eastern Caribbean & Perfect Day Cruise From Fort Lauderdale, Florida

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

Published prices from

$1,188

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Aboard

Coral Princess

From

Fort Lauderdale, Florida

Published prices from

$1,249

per person*

taxes & fees included

Historic buildings in Galveston, Texas.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

14-night Carnival Journeys Cruise - Eastern Caribbean From Galveston, Texas

Aboard

Carnival Dream

From

Galveston, Texas

A beautiful autumn landscape in Saguenay with a river flowing under a bridge, surrounded by hillsides adorned with houses and vibrant yellow, orange, and red fall foliage.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

25-night Canada & Caribbean Isles Voyage From Montreal, Quebec

Aboard

Vista

From

Montreal, Quebec

Published prices from

$11,949

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

25-night Canada & Caribbean Cruise From Montreal, Quebec

Aboard

Silver Shadow

From

Montreal, Quebec

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 Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

14-night An Extended Journey Of Maritime Soul & Island Zest From Miami, Florida

Aboard

EXPLORA III

From

Miami, Florida

Published prices from

$12,280

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Caribbean Enchantment Voyage From New York City, New York

Aboard

Vista

From

New York City, New York

Published prices from

$3,930

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 $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$5,008

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 Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Aboard

Coral Princess

From

Fort Lauderdale, Florida

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

25 nights South Caribbean From Civitavecchia, Rome, Italy

Aboard

MSC Opera

From

Civitavecchia, Rome, Italy

Published prices from

$5,232

per person*

taxes & fees included

St. Peter's Basilica, Rome cityscape at sunset.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

18 nights South Caribbean From Civitavecchia, Rome, Italy

Aboard

MSC Opera

From

Civitavecchia, Rome, Italy

Published prices from

$935

per person*

taxes & fees included

A beautiful image of a narrow, stone-paved street in a medieval Italian village near Livorno, adorned with ivy-covered walls, potted plants, and colorful flowers, giving a feeling of tranquility.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

17 nights South Caribbean From Genoa, Italy

Aboard

MSC Opera

From

Genoa, Italy

Published prices from

$700

per person*

taxes & fees included

A scenic view of Catalina Island, Dominican Republic, with a pristine sandy beach lined with palm trees and the calm turquoise waters of the Caribbean Sea in the background.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

24 nights South Caribbean From Genoa, Italy

Aboard

MSC Opera

From

Genoa, Italy

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

20 nights South Caribbean From Genoa, Italy

Aboard

MSC Opera

From

Genoa, Italy

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

17 nights South Caribbean From Florence/Pisa (Livorno), Italy

Aboard

MSC Opera

From

Florence/Pisa (Livorno), Italy

Notre-Dame Basilica in Montreal.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

16-night Epic Atlantic Escapade Cruise From Montreal, Quebec

Aboard

Seven Seas Splendor

From

Montreal, Quebec

Published prices from

$15,099

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 $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Eastern & Western Caribbean Cruise: Leeward Islands & Mexico From Miami, Florida

Aboard

Zuiderdam

From

Miami, Florida

Published prices from

$1,879

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
Holland America logo

11-night Eastern Caribbean Cruise: Windward & Leeward Islands From Miami, Florida

Aboard

Zuiderdam

From

Miami, Florida

Published prices from

$1,154

per person*

taxes & fees included

A secluded cove with white sand and turquoise water on Half Moon Cay, Bahamas, surrounded by jagged, rocky cliffs and a serene blue ocean under a partly cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Western & Eastern Caribbean Cruise: Mexico & Leeward Islands From Fort Lauderdale, Florida

Aboard

Rotterdam

From

Fort Lauderdale, Florida

Published prices from

$1,904

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*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

16 nights South Caribbean From Florence/Pisa (Livorno), Italy

Aboard

MSC Opera

From

Florence/Pisa (Livorno), Italy

Published prices from

$1,159

per person*

taxes & fees included

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

19 nights South Caribbean From Genoa, Italy

Aboard

MSC Opera

From

Genoa, Italy

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

16 nights South Caribbean From Genoa, Italy

Aboard

MSC Opera

From

Genoa, Italy

Published prices from

$949

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
Carnival Cruise Line

14-night Carnival Journeys Cruise - Southern Caribbean From Baltimore, Maryland

Aboard

Carnival Pride

From

Baltimore, Maryland

Published prices from

$1,871

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

Published prices from

$12,000

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.