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71 Results

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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

Miami
St. Maarten (Philipsburg)
St. John's
Fort de France
Roseau
+8 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

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
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

22 Sailings

Nov 1, 2026 - Mar 16, 2028

22 Sailings

Nov 1, 2026 - Mar 16, 2028

Published prices from

$2,081

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
Royal Caribbean logo

9-night Southern Caribbean & Perfect Day Cruise From Miami, Florida

Miami
Willemstad
Oranjestad
Cabo Rojo
Perfect Day at CocoCay

Aboard

Freedom of the Seas

From

Miami, Florida

3 Sailings

Nov 5, 2026 - Jan 28, 2027

3 Sailings

Nov 5, 2026 - Jan 28, 2027

Published prices from

$664

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.

12-night Panama Canal Cruise: Bahamas & Costa Rica From Miami, Florida

Miami
Great Stirrup Cay
Cabo Rojo
Willemstad
Oranjestad
+5 more

Aboard

Norwegian Sun

From

Miami, Florida

2 Sailings

Nov 6 - Dec 21, 2026

2 Sailings

Nov 6 - Dec 21, 2026

Published prices from

$1,169

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

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*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

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

Miami
Kralendijk
Willemstad
Oranjestad
Cabo Rojo
+2 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

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

8-nights Southern Caribbean & Perfect Day Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Willemstad
Oranjestad
Cabo Rojo
Perfect Day at CocoCay

Aboard

Legend of the Seas

From

Fort Lauderdale, Florida

11 Sailings

Nov 14, 2026 - Apr 17, 2027

11 Sailings

Nov 14, 2026 - Apr 17, 2027

Published prices from

$1,789

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*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

9-night Southern Caribbean Cruise From Port Canaveral, Florida

Port Canaveral
Nassau
Cabo Rojo
Oranjestad
Willemstad
+2 more

Aboard

Explorer of the Seas

From

Port Canaveral, Florida

2 Sailings

Nov 18, 2026 - Feb 24, 2027

2 Sailings

Nov 18, 2026 - Feb 24, 2027

Published prices from

$855

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

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
Royal Caribbean logo

9-night Southern Caribbean & Perfect Day Cruise From Port Canaveral, Florida

Port Canaveral
Bimini
Willemstad
Oranjestad
Cabo Rojo
+2 more

Aboard

Explorer of the Seas

From

Port Canaveral, Florida

3 Sailings

Dec 2, 2026 - Jan 27, 2027

3 Sailings

Dec 2, 2026 - Jan 27, 2027

Published prices from

$1,319

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
Royal Caribbean logo

9-night Southern Caribbean Cruise From Miami, Florida

Miami
Willemstad
Oranjestad
Cabo Rojo
Perfect Day at CocoCay

Aboard

Freedom of the Seas

From

Miami, Florida

7 Sailings

Dec 3, 2026 - Feb 24, 2028

7 Sailings

Dec 3, 2026 - Feb 24, 2028

Published prices from

$853

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*+ 2 more offers
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

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*+ 2 more offers
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

13 Sailings

Dec 3, 2026 - Mar 16, 2028

13 Sailings

Dec 3, 2026 - Mar 16, 2028

Published prices from

$729

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

Yellow kayak on sandy beach in Puerto Vallarta, Mexico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

18-night Panama Canal Voyage: Colombia, Costa Rica & Mexico From Miami, Florida

Miami
Cabo Rojo
Cartagena (Colombia)
Panama Canal
Puntarenas
+5 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

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
Royal Caribbean logo

8-night Southern Caribbean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Nassau
Cabo Rojo
Willemstad
Oranjestad

Aboard

Adventure of the Seas

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$2,139

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.

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

Miami
Great Stirrup Cay
Cabo Rojo
Oranjestad
Willemstad
+5 more

Aboard

Norwegian Jewel

From

Miami, Florida

1 Sailing

Dec 23, 2026

1 Sailing

Dec 23, 2026

Published prices from

$1,599

per person*

taxes & fees included

The welcome sign with a hot air balloon, and the Daredevil Tower waterslides in the background at Cococay, Royal Caribbean's private island.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

8-nights Southern Caribbean & Perfect Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Cabo Rojo
Perfect Day at CocoCay

Aboard

Legend of the Seas

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Published prices from

$3,599

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.

10-night Caribbean Round-Trip Tampa Cruise: Curacao & Dominican Republic From Tampa, Florida

Tampa
Cabo Rojo
Willemstad
Falmouth (Jamaica)
Grand Cayman (George Town)

Aboard

Norwegian Gem

From

Tampa, Florida

1 Sailing

Jan 4, 2027

1 Sailing

Jan 4, 2027

Published prices from

$899

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.

10-night Caribbean Round-Trip Tampa Cruise: Curacao, Aruba & Dominican Republic From Tampa, Florida

Tampa
Cabo Rojo
Willemstad
Oranjestad
Falmouth (Jamaica)
+2 more

Aboard

Norwegian Gem

From

Tampa, Florida

1 Sailing

Jan 18, 2027

1 Sailing

Jan 18, 2027

Published prices from

$1,189

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

12-night Panama Canal Round-trip Miami Cruise: Bahamas & Costa Rica From Miami, Florida

Miami
Great Stirrup Cay
Cabo Rojo
Willemstad
Oranjestad
+5 more

Aboard

Norwegian Sun

From

Miami, Florida

2 Sailings

Jan 25 - Mar 1, 2027

2 Sailings

Jan 25 - Mar 1, 2027

Published prices from

$1,499

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

9-night Bahamas Round-trip Tampa Cruise: Great Stirrup Cay & Key West From Tampa, Florida

Tampa
Key West
Great Stirrup Cay
Cabo Rojo
Falmouth (Jamaica)
+2 more

Aboard

Norwegian Gem

From

Tampa, Florida

1 Sailing

Feb 12, 2027

1 Sailing

Feb 12, 2027

Published prices from

$1,189

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
Oceania Cruises

20-night Sju to Mia Voyage From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
St. John's
+10 more

Aboard

Allura

From

San Juan, Puerto Rico

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$11,349

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
Oceania Cruises

12-night Radiant Island Retreats Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Falmouth (Jamaica)
Oranjestad
Willemstad
+4 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Feb 27, 2027

1 Sailing

Feb 27, 2027

Published prices from

$6,799

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

18-night Eastern/Southern Caribbean Cruise: Amber Cove & Abc Islands From Miami, Florida

Miami
Half Moon Cay
Amber Cove
Grand Turk
Nassau
+5 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Mar 6, 2027

1 Sailing

Mar 6, 2027

Published prices from

$2,074

per person*

taxes & fees included

    • Showing results 1 - 24 of 71

*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.