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146 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

A scenic coastal view in Curaçao featuring houses with orange roofs on a cliffside overlooking a rocky beach with beautiful turquoise Caribbean water.
Save up to 55% on Select Sailings*
Carnival Cruise Line Logo

8-night Southern Caribbean Cruise From Miami, Florida

Miami
Curacao
Kralendijk
Oranjestad

Aboard

Carnival Horizon

From

Miami, Florida

13 Sailings

Nov 7, 2026 - Apr 24, 2027

13 Sailings

Nov 7, 2026 - Apr 24, 2027

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

8-night Aruba, Curacao & Bonaire Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Willemstad
Kralendijk

Aboard

Celebrity Silhouette

From

Fort Lauderdale, Florida

15 Sailings

Nov 7, 2026 - Apr 1, 2028

15 Sailings

Nov 7, 2026 - Apr 1, 2028

Published prices from

$932

per person*

taxes & fees included

A serene hiking path winds through a dense, lush green jungle with a towering tree on the left, capturing the essence of an adventure in nature.
Holland America logo

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

Ft. Lauderdale
Half Moon Cay
Oranjestad
Cartagena (Colombia)
Cristobal (Colon)
+8 more

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

2 Sailings

Nov 8, 2026 - Mar 21, 2027

2 Sailings

Nov 8, 2026 - Mar 21, 2027

Published prices from

$1,709

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

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Lisbon
Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$7,989

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

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
Royal Caribbean logo

10-night Southern Caribbean Cruise From Colon, Panama

Colon (Panama)
Kralendijk
Oranjestad
Willemstad
Port of Spain
+2 more

Aboard

Grandeur of the Seas

From

Colon, Panama

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Historic buildings in Galveston, Texas.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night Sapphire Sea Dreams Cruise From Miami, Florida

Miami
Old Bahama Channel
Willemstad
Oranjestad
Kralendijk
+7 more

Aboard

Seven Seas Splendor

From

Miami, Florida

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

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.
Holland America logo

9-night Southern Caribbean & Abc Islands With History Channel Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Kralendijk
Willemstad
Half Moon Cay

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

4 Sailings

Nov 20, 2026 - Apr 2, 2027

4 Sailings

Nov 20, 2026 - Apr 2, 2027

Published prices from

$744

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

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

Ft. Lauderdale
Kralendijk
Willemstad
Half Moon Cay
St. Maarten (Philipsburg)
+7 more

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$1,694

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

11-nights Panama Canal & Southern Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Cartagena (Colombia)
Panama Canal
Colon (Panama)
Oranjestad
+3 more

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

2 Sailings

Nov 23, 2026 - Mar 8, 2027

2 Sailings

Nov 23, 2026 - Mar 8, 2027

Published prices from

$2,032

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+11 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$8,272

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+5 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$4,792

per person*

taxes & fees included

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Anse Mitan
Pigeon Island
Castries
The Pitons
+9 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$4,768

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

8-night Aruba, Bonaire & Curacao Cruise From Miami, Florida

Miami
Oranjestad
Kralendijk
Willemstad

Aboard

Celebrity Xcel

From

Miami, Florida

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

Published prices from

$7,608

per person*

taxes & fees included

An aerial view of the Old Bahama Channel, showing a small white boat sailing on the stunning turquoise waters and small rocky islands of the Caribbean.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Sunset Serenity Cruise From Miami, Florida

Miami
Old Bahama Channel
Oranjestad
Willemstad
Kralendijk
+4 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Dec 1, 2026

1 Sailing

Dec 1, 2026

Published prices from

$7,899

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 breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+10 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$5,244

per person*

taxes & fees included

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+5 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$2,760

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
Regent Seven Seas Cruises.

14-night Caribbean Celebration Cruise From Tampa, Florida

Tampa
Grand Cayman (George Town)
Ocho Rios
Oranjestad
Willemstad
+6 more

Aboard

Seven Seas Mariner

From

Tampa, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$12,399

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

12-night Southern Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Basseterre
Castries
Bridgetown (Barbados)
Willemstad
+3 more

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$3,302

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 Caribbean Celebration Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Montego Bay
Oranjestad
Willemstad
+5 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$4,699

per person*

taxes & fees included

    • Showing results 1 - 24 of 146

*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.