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105 Results

Taxes and fees included in all prices shown

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Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
MSC Cruises logo

10 nights Caribbean Mini Cruise From Port Canaveral, Florida

Port Canaveral
Nassau
Ocean Cay
Ocho Rios
George Town

Aboard

MSC Seashore

From

Port Canaveral, Florida

3 Sailings

Oct 15 - Dec 17, 2026

3 Sailings

Oct 15 - Dec 17, 2026

Published prices from

$707

per person*

taxes & fees included

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

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

Galveston
Key West
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
+5 more

Aboard

Carnival Dream

From

Galveston, Texas

2 Sailings

Oct 17, 2026 - Jan 16, 2027

2 Sailings

Oct 17, 2026 - Jan 16, 2027

Published prices from

$1,489

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

5 nights West Caribbean From Miami, Florida

Miami
George Town
Ocho Rios

Aboard

MSC Poesia

From

Miami, Florida

2 Sailings

Oct 17, 2026 - Oct 16, 2027

2 Sailings

Oct 17, 2026 - Oct 16, 2027

Published prices from

$398

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*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

15 nights West Caribbean From Miami, Florida

Miami
George Town
Ocho Rios
Kralendijk
Oranjestad
+3 more

Aboard

MSC Poesia

From

Miami, Florida

2 Sailings

Oct 17, 2026 - Oct 16, 2027

2 Sailings

Oct 17, 2026 - Oct 16, 2027

Published prices from

$1,219

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*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

11 nights West Caribbean From Port Canaveral, Florida

Port Canaveral
Nassau
Ocho Rios
George Town
Ocean Cay

Aboard

MSC Seashore

From

Port Canaveral, Florida

2 Sailings

Oct 18 - Nov 22, 2026

2 Sailings

Oct 18 - Nov 22, 2026

Published prices from

$692

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
MSC Cruises logo

10 nights West Caribbean From Miami, Florida

Miami
Willemstad
Kralendijk
Oranjestad
Cabo Rojo
+2 more

Aboard

MSC Poesia

From

Miami, Florida

14 Sailings

Oct 22, 2026 - Mar 16, 2028

14 Sailings

Oct 22, 2026 - Mar 16, 2028

Published prices from

$729

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*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

21 nights West Caribbean From Miami, Florida

Miami
Ocho Rios
Cartagena (Colombia)
Colon (Panama)
Puerto Limon
+7 more

Aboard

MSC Poesia

From

Miami, Florida

23 Sailings

Oct 22, 2026 - Mar 16, 2028

23 Sailings

Oct 22, 2026 - Mar 16, 2028

Published prices from

$2,081

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*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Southern Caribbean & Panama Canal: Abc Islands Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Cabo Rojo
Willemstad
Oranjestad
Half Moon Cay
+8 more

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

1 Sailing

Oct 30, 2026

1 Sailing

Oct 30, 2026

Published prices from

$1,999

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*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

11 nights West Caribbean From Miami, Florida

Miami
Ocho Rios
Cartagena (Colombia)
Colon (Panama)
Puerto Limon
+3 more

Aboard

MSC Poesia

From

Miami, Florida

15 Sailings

Nov 1, 2026 - Mar 26, 2028

15 Sailings

Nov 1, 2026 - Mar 26, 2028

Published prices from

$1,053

per person*

taxes & fees included

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern/Eastern Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Princess Cays®
Grand Turk
Nassau
Grand Cayman (George Town)
+3 more

Aboard

Regal Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 8, 2026 - Mar 6, 2027

10 Sailings

Nov 8, 2026 - Mar 6, 2027

Published prices from

$2,753

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

17-night Western Caribbean Cruise: Greater Antilles & Honduras From Miami, Florida

Miami
Kralendijk
Willemstad
Oranjestad
Cabo Rojo
+6 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$1,429

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

21 nights East Caribbean From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Basseterre
Philipsburg
St. John's
+9 more

Aboard

MSC Poesia

From

Miami, Florida

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$2,435

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

8-night Southern Caribbean With Abc Islands Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Grand Cayman (George Town)
Ocho Rios
Oranjestad

Aboard

Regal Princess

From

Fort Lauderdale, Florida

4 Sailings

Nov 14, 2026 - Feb 6, 2027

4 Sailings

Nov 14, 2026 - Feb 6, 2027

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

14-night Western & Eastern Caribbean Cruise: Mexico & Bahamas From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Ocho Rios
Grand Cayman (George Town)
Cozumel
+4 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

2 Sailings

Nov 14 - Dec 5, 2026

2 Sailings

Nov 14 - Dec 5, 2026

Published prices from

$989

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

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

Ft. Lauderdale
Half Moon Cay
Ocho Rios
Grand Cayman (George Town)
Cozumel

Aboard

Eurodam

From

Fort Lauderdale, Florida

3 Sailings

Nov 14, 2026 - Feb 6, 2027

3 Sailings

Nov 14, 2026 - Feb 6, 2027

Published prices from

$534

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Cozumel From Port Canaveral, Florida

Port Canaveral
Great Stirrup Cay
Ocho Rios
Cozumel

Aboard

Norwegian Epic

From

Port Canaveral, Florida

20 Sailings

Nov 15, 2026 - Mar 28, 2027

20 Sailings

Nov 15, 2026 - Mar 28, 2027

Published prices from

$379

per person*

taxes & fees included

A panoramic shot of the colorful waterfront houses and palm trees of Key West, Florida, reflecting on the calm, turquoise water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Western & Eastern Caribbean Cruise: Mexico & Bahamas From Miami, Florida

Miami
Key West
Ocho Rios
Grand Cayman (George Town)
Cozumel
+5 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$989

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
Holland America logo

7-night Western Caribbean Cruise: Greater Antilles & Mexico From Miami, Florida

Miami
Key West
Ocho Rios
Grand Cayman (George Town)
Cozumel

Aboard

Zuiderdam

From

Miami, Florida

2 Sailings

Nov 21 - Dec 12, 2026

2 Sailings

Nov 21 - Dec 12, 2026

Published prices from

$584

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*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

6-night Western Caribbean Cruise From Miami, Florida

Miami
Grand Cayman (George Town)
Ocho Rios
Celebration Key

Aboard

Carnival Sunrise

From

Miami, Florida

2 Sailings

Nov 23, 2026 - Nov 22, 2027

2 Sailings

Nov 23, 2026 - Nov 22, 2027

Published prices from

$1,034

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern & Western Caribbean Cruise: San Juan & Mexico From Fort Lauderdale, Florida

Ft. Lauderdale
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
Half Moon Cay
+4 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

2 Sailings

Nov 28, 2026 - Feb 20, 2027

2 Sailings

Nov 28, 2026 - Feb 20, 2027

Published prices from

$1,114

per person*

taxes & fees included

A breathtaking view of the Los Morrillos Lighthouse and the rugged coastline of Cabo Rojo, Puerto Rico, with dramatic cliffs and turquoise water.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
MSC Cruises logo

20 nights West Caribbean From Miami, Florida

Miami
Willemstad
Oranjestad
Cabo Rojo
Ocho Rios
+3 more

Aboard

MSC Poesia

From

Miami, Florida

1 Sailing

Dec 3, 2026

1 Sailing

Dec 3, 2026

Published prices from

$1,596

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
Holland America logo

14-night Eastern & Western Caribbean Cruise: San Juan & Mexico From Miami, Florida

Miami
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
Half Moon Cay
+4 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$1,034

per person*

taxes & fees included

A scenic beach in Montego Bay, Jamaica, with a long line of palm trees and resort hotels along the white sand, and a large school of fish visible in the clear blue water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

17-night Tropical Sparkle & Holiday Cheer Cruise From Galveston, Texas

Galveston
Montego Bay
Ocho Rios
Punta Cana
San Juan
+6 more

Aboard

Seven Seas Splendor

From

Galveston, Texas

1 Sailing

Dec 11, 2026

1 Sailing

Dec 11, 2026

Published prices from

$12,799

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Western & Eastern Caribbean Cruise: Mexico & Bahamas Holiday From Miami, Florida

Miami
Half Moon Cay
Ocho Rios
Grand Cayman (George Town)
Cozumel
+4 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$1,079

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

15-night An Extended Journey Through Wild Beauty And Tropical Festivities From San Juan, Puerto Rico

San Juan
Road Bay
St. John's
Basseterre
Grand Turk
+7 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$10,985

per person*

taxes & fees included

    • Showing results 1 - 24 of 105

*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.