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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

Published prices from

$1,789

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

Miami
St. Maarten (Philipsburg)
St. John's
Fort de France
Roseau
+4 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$1,054

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

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

$1,694

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

$1,749

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

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

Ft. Lauderdale
St. Maarten (Philipsburg)
St. John's
Roseau
Castries
+4 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

6 Sailings

Nov 10, 2026 - Mar 16, 2027

6 Sailings

Nov 10, 2026 - Mar 16, 2027

Published prices from

$1,104

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

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

Ft. Lauderdale
Half Moon Cay
Amber Cove
Grand Turk
Key West
+3 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$1,074

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
Holland America logo

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

Miami
Half Moon Cay
Amber Cove
Grand Turk
Nassau
+3 more

Aboard

Zuiderdam

From

Miami, Florida

2 Sailings

Nov 28, 2026 - Nov 27, 2027

2 Sailings

Nov 28, 2026 - Nov 27, 2027

Published prices from

$994

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

7-night Eastern Caribbean Cruise: San Juan & St. Thomas From Fort Lauderdale, Florida

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

Aboard

Eurodam

From

Fort Lauderdale, Florida

3 Sailings

Nov 28, 2026 - Jan 29, 2028

3 Sailings

Nov 28, 2026 - Jan 29, 2028

Published prices from

$634

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

7-night Eastern Caribbean Cruise: San Juan & St. Thomas From Miami, Florida

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

Aboard

Zuiderdam

From

Miami, Florida

2 Sailings

Dec 5, 2026 - Dec 4, 2027

2 Sailings

Dec 5, 2026 - Dec 4, 2027

Published prices from

$634

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern Caribbean Cruise: Bahamas & San Juan Holiday From Fort Lauderdale, Florida

Ft. Lauderdale
Nassau
Grand Turk
Amber Cove
Half Moon Cay
+3 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$1,114

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

$2,139

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

7-night Eastern Caribbean Holiday Cruise: San Juan & St. Thomas From Fort Lauderdale, Florida

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

Aboard

Eurodam

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$734

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 Caribbean Cruise: Bahamas & San Juan Holiday From Miami, Florida

Miami
Amber Cove
Grand Turk
Half Moon Cay
Key West
+3 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$1,429

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 Eastern/Western Caribbean Cruise: San Juan & Mexico Holiday 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

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$1,434

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

$2,179

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean Holiday Cruise: Windward & Leeward Islands From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Roseau
Castries
+4 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$1,554

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 Eastern Caribbean Holiday Cruise: San Juan & St. Thomas From Miami, Florida

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

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Published prices from

$1,034

per person*

taxes & fees included

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

14-night Eastern Caribbean Holiday Cruise: Bahamas & San Juan From Fort Lauderdale, Florida

Ft. Lauderdale
Nassau
Grand Turk
Amber Cove
Half Moon Cay
+3 more

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Published prices from

$1,429

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
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

Nieuw Statendam

From

Fort Lauderdale, Florida

4 Sailings

Jan 3 - Mar 7, 2027

4 Sailings

Jan 3 - Mar 7, 2027

Published prices from

$1,419

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

7-night Eastern Caribbean Cruise: San Juan & St. Thomas From Fort Lauderdale, Florida

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

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

5 Sailings

Jan 3 - Mar 28, 2027

5 Sailings

Jan 3 - Mar 28, 2027

Published prices from

$734

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

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

Ft. Lauderdale
Nassau
Half Moon Cay
Grand Turk
Amber Cove
+3 more

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

4 Sailings

Jan 17 - Mar 21, 2027

4 Sailings

Jan 17 - Mar 21, 2027

Published prices from

$1,509

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 Panama Canal & Eastern Caribbean Cruise: U.S. Virgin Islands From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Oranjestad
Cartagena (Colombia)
Cristobal (Colon)
+10 more

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

2 Sailings

Jan 17 - Feb 28, 2027

2 Sailings

Jan 17 - Feb 28, 2027

Published prices from

$2,654

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

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

Ft. Lauderdale
Nassau
Grand Turk
Amber Cove
Half Moon Cay
+3 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

1 Sailing

Jan 23, 2027

1 Sailing

Jan 23, 2027

Published prices from

$1,379

per person*

taxes & fees included

    • Showing results 1 - 24 of 51

*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.