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104 Results

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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

Ft. Lauderdale
Half Moon Cay
Falmouth (Jamaica)
Grand Cayman (George Town)
Mahogany Bay
+9 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

6 Sailings

Oct 31, 2026 - Mar 6, 2027

6 Sailings

Oct 31, 2026 - Mar 6, 2027

Published prices from

$1,654

per person*

taxes & fees included

An aerial view of the historic town of Falmouth, Jamaica, showing a coastal promenade along the turquoise sea, colorful colonial-era buildings, and lush green hills in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

10-night Western Caribbean Cruise: Greater Antilles, Belize & Mexico From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Falmouth (Jamaica)
Grand Cayman (George Town)
Mahogany Bay
+3 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

7 Sailings

Oct 31, 2026 - Mar 6, 2027

7 Sailings

Oct 31, 2026 - Mar 6, 2027

Published prices from

$799

per person*

taxes & fees included

Ornate ironwork balconies in the French Quarter of New Orleans, Louisiana.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean Cruise From New Orleans, Louisiana

New Orleans
Cozumel
Grand Cayman (George Town)
Falmouth (Jamaica)

Aboard

Mariner of the Seas

From

New Orleans, Louisiana

36 Sailings

Nov 7, 2026 - Apr 15, 2028

36 Sailings

Nov 7, 2026 - Apr 15, 2028

Published prices from

$556

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*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean & Perfect Day Cruise From Miami, Florida

Miami
Perfect Day at CocoCay
Grand Cayman (George Town)
Falmouth (Jamaica)

Aboard

Independence of the Seas

From

Miami, Florida

6 Sailings

Nov 8, 2026 - Apr 25, 2027

6 Sailings

Nov 8, 2026 - Apr 25, 2027

Published prices from

$554

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

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

Ft. Lauderdale
St. Maarten (Philipsburg)
St. John's
Roseau
Castries
+9 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

5 Sailings

Nov 10, 2026 - Feb 23, 2027

5 Sailings

Nov 10, 2026 - Feb 23, 2027

Published prices from

$1,669

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Dutchman's Caribbean Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Falmouth (Jamaica)
Oranjestad
Willemstad
+5 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$6,499

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to 60% off 2nd Guest + Kids Sail Free*
Royal Caribbean logo

7-night Western Caribbean & Perfect Day Cruise From Miami, Florida

Miami
Nassau
Perfect Day at CocoCay
Falmouth (Jamaica)

Aboard

Allure of the Seas

From

Miami, Florida

7 Sailings

Nov 15, 2026 - Apr 18, 2027

7 Sailings

Nov 15, 2026 - Apr 18, 2027

Published prices from

$633

per person*

taxes & fees included

A stunning shot of a small, natural tunnel in the cliffs of the rugged coastline near Puerto Limon, Costa Rica, with a gnarled tree branch reaching across the top and water flowing through.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

11-night Panama Canal Cruise: Jamaica & Costa Rica From Miami, Florida

Miami
Great Stirrup Cay
Cartagena (Colombia)
Panama Canal
Colon (Panama)
+4 more

Aboard

Norwegian Sun

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$769

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean Cruise From Miami, Florida

Miami
Nassau
Falmouth (Jamaica)
Grand Cayman (George Town)
Cozumel

Aboard

Independence of the Seas

From

Miami, Florida

2 Sailings

Nov 22, 2026 - Feb 19, 2028

2 Sailings

Nov 22, 2026 - Feb 19, 2028

Published prices from

$815

per person*

taxes & fees included

Sunshine Skyway Bridge near Tampa, Florida at sunset.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

12-night Caribbean Round-Trip Tampa Cruise: Jamaica & Puerto Rico From Tampa, Florida

Tampa
San Juan
Roadtown
Basseterre
St. Maarten (Philipsburg)
+4 more

Aboard

Norwegian Gem

From

Tampa, Florida

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

Published prices from

$909

per person*

taxes & fees included

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

10-night Caribbean Cruise: Curacao, Aruba & Dominican Republic From Miami, Florida

Miami
Great Stirrup Cay
Cabo Rojo
Willemstad
Oranjestad
+3 more

Aboard

Norwegian Jewel

From

Miami, Florida

4 Sailings

Nov 28, 2026 - Mar 19, 2027

4 Sailings

Nov 28, 2026 - Mar 19, 2027

Published prices from

$719

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

11-night Panama Canal Round-trip Miami Cruise: Jamaica & Costa Rica From Miami, Florida

Miami
Great Stirrup Cay
Cartagena (Colombia)
Panama Canal
Colon (Panama)
+4 more

Aboard

Norwegian Sun

From

Miami, Florida

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$769

per person*

taxes & fees included

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

11-night Caribbean Round-Trip Tampa Cruise: Bahamas & Jamaica From Tampa, Florida

Tampa
Great Stirrup Cay
Cabo Rojo
Oranjestad
Willemstad
+3 more

Aboard

Norwegian Gem

From

Tampa, Florida

2 Sailings

Dec 10, 2026 - Feb 21, 2027

2 Sailings

Dec 10, 2026 - Feb 21, 2027

Published prices from

$979

per person*

taxes & fees included

Immaculate Conception Cathedral in Colon.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

11-night Panama Canal Cruise: Mexico, Jamaica & Costa Rica From Miami, Florida

Miami
Falmouth (Jamaica)
Cartagena (Colombia)
Panama Canal
Colon (Panama)
+4 more

Aboard

Norwegian Sun

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$1,029

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*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Western & Eastern Caribbean Holiday Cruise: Belize & Mexico From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Falmouth (Jamaica)
Grand Cayman (George Town)
Mahogany Bay
+9 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$2,059

per person*

taxes & fees included

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

6-night Western Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Falmouth (Jamaica)
Grand Cayman (George Town)
Nassau

Aboard

Adventure of the Seas

From

Fort Lauderdale, Florida

6 Sailings

Dec 13, 2026 - Apr 4, 2027

6 Sailings

Dec 13, 2026 - Apr 4, 2027

Published prices from

$430

per person*

taxes & fees included

An aerial view of a long pier with a red trolley, stretching from the sandy beach of Bimini island to a collection of colorful houses, with clear turquoise water all around.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean Holiday Cruise From Miami, Florida

Miami
Bimini
Grand Cayman (George Town)
Ocho Rios
Falmouth (Jamaica)

Aboard

Independence of the Seas

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$1,444

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
MSC Cruises logo

14 nights East Caribbean From Miami, Florida

Miami
Ocean Cay
San Juan
Puerto Plata
Falmouth (Jamaica)
+3 more

Aboard

MSC Seaside

From

Miami, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$1,985

per person*

taxes & fees included

An aerial view of the historic town of Falmouth, Jamaica, showing a coastal promenade along the turquoise sea, colorful colonial-era buildings, and lush green hills in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean & Perfect Day Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Nassau
Perfect Day at CocoCay
Falmouth (Jamaica)

Aboard

Oasis of the Seas

From

Fort Lauderdale, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$1,987

per person*

taxes & fees included

A panoramic sunset view of a beautiful sandy beach on Grand Bahama Island, with palm trees silhouetted against a dramatic sky filled with vibrant pink and purple clouds.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Caribbean Holiday Cruise From Port Canaveral, Florida

Port Canaveral
Grand Bahama Island
Falmouth (Jamaica)
Grand Cayman (George Town)
Cozumel

Aboard

Explorer of the Seas

From

Port Canaveral, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$2,028

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

21-night Eastern & Western Caribbean Holiday Cruise: Belize & Mexico From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Roseau
Castries
+9 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$2,139

per person*

taxes & fees included

An aerial view of the historic town of Falmouth, Jamaica, showing a coastal promenade along the turquoise sea, colorful colonial-era buildings, and lush green hills in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Western Carib & Perfect Day Holiday Cruise From Miami, Florida

Miami
Perfect Day at CocoCay
Nassau
Falmouth (Jamaica)
Grand Cayman (George Town)

Aboard

Independence of the Seas

From

Miami, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Published prices from

$2,177

per person*

taxes & fees included

An idyllic, wide-angle photo of a beautiful white sand beach at Ocean Cay MSC Marine Reserve in The Bahamas. The foreground features soft, white sand leading to shallow turquoise water. Several upright palm trees are visible on the left, casting shadows, and the background shows the vast, clear blue ocean meeting a horizon under a sky with scattered white clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

7 nights West Caribbean From Miami, Florida

Miami
Ocean Cay
Falmouth (Jamaica)
George Town
Cozumel

Aboard

MSC Seaside

From

Miami, Florida

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$1,309

per person*

taxes & fees included

An idyllic, wide-angle photo of a beautiful white sand beach at Ocean Cay MSC Marine Reserve in The Bahamas. The foreground features soft, white sand leading to shallow turquoise water. Several upright palm trees are visible on the left, casting shadows, and the background shows the vast, clear blue ocean meeting a horizon under a sky with scattered white clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

11 nights West Caribbean From Miami, Florida

Miami
Ocean Cay
Falmouth (Jamaica)
George Town
Cozumel
+2 more

Aboard

MSC Seaside

From

Miami, Florida

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$1,583

per person*

taxes & fees included

An aerial shot of the Florida Keys at sunset, showing a long highway stretching along the thin strip of land, with the calm, turquoise Florida Strait on one side and a lush mangrove coastline on the other.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

11-night Azure Elegance Cruise From Miami, Florida

Miami
Florida Strait
Merida (Progreso)
Santo Tomas de Castilla
Harvest Caye
+4 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

    • Showing results 1 - 24 of 104

*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.