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Five cruise ships in the port with very blue water surrounding them

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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

7-night Southern Caribbean Cruise From Colon, Panama

Colon (Panama)
Cartagena (Colombia)
Santa Marta
Willemstad
Oranjestad

Aboard

Grandeur of the Seas

From

Colon, Panama

38 Sailings

Oct 31, 2026 - Apr 22, 2028

38 Sailings

Oct 31, 2026 - Apr 22, 2028

Published prices from

$993

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 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

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

$954

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

$1,654

per person*

taxes & fees included

Belém Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

24-night Star Collector: Classic Crossing To Spain & More Cruise From Barcelona, Spain

Barcelona
Barcelona (Tarragona)
Palma de Mallorca
Valencia
Cartagena (Spain)
+5 more

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$7,382

per person*

taxes & fees included

A panoramic view of a long, gray pier extending into the calm turquoise waters of St. Croix, US Virgin Islands, with the town and a lush green mountain in the background.
FREE Spa Treatment*+ 1 more offer
Royal Caribbean logo

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. Croix
St. Maarten (Philipsburg)
St. John's
Fort de France
+2 more

Aboard

Rhapsody of the Seas

From

San Juan, Puerto Rico

37 Sailings

Oct 31, 2026 - Apr 15, 2028

37 Sailings

Oct 31, 2026 - Apr 15, 2028

Published prices from

$530

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

14-night Carnival Journeys Cruise - Southern Caribbean From Baltimore, Maryland

Baltimore
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
Oranjestad
+3 more

Aboard

Carnival Pride

From

Baltimore, Maryland

2 Sailings

Nov 1, 2026 - Jan 10, 2027

2 Sailings

Nov 1, 2026 - Jan 10, 2027

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

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
Roadtown
St. John's
Fort de France
St. Vincent (Kingstown)
+2 more

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

42 Sailings

Nov 1, 2026 - Apr 16, 2028

42 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$521

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

7-night Southern Caribbean Cruise From Cartagena, Colombia

Cartagena (Colombia)
Willemstad
Oranjestad
Colon (Panama)

Aboard

Grandeur of the Seas

From

Cartagena, Colombia

34 Sailings

Nov 1, 2026 - Apr 16, 2028

34 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$1,070

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
Oceania Cruises

47-night Footsteps of Columbus Voyage From Barcelona, Spain

Barcelona
Palma de Mallorca
Alicante
Cartagena (Spain)
Malaga
+24 more

Aboard

Insignia

From

Barcelona, Spain

1 Sailing

Nov 2, 2026

1 Sailing

Nov 2, 2026

Published prices from

$28,049

per person*

taxes & fees included

A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Barcelona
Mystery Island (Aneityum)
Malaga
Tangier
Casablanca
+3 more

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Nov 4, 2026

1 Sailing

Nov 4, 2026

Published prices from

$7,587

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
Viking

10-night West Indies Explorer Cruise From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Castries
Bridgetown (Barbados)
+4 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

25 Sailings

Nov 5, 2026 - Jan 29, 2029

25 Sailings

Nov 5, 2026 - Jan 29, 2029

Published prices from

$3,599

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

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

16-night Panama Canal - Ocean To Ocean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Panama Canal
Fuerte Amador (Panama City)
Puntarenas
+5 more

Aboard

Sapphire Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 6, 2026

1 Sailing

Nov 6, 2026

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

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

12-night Southern Caribbean Islander Cruise From New York City, New York

New York City
St. Maarten (Philipsburg)
Basseterre
Castries
Curacao
+3 more

Aboard

Majestic Princess

From

New York City, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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 beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+3 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

3 Sailings

Nov 7 - Dec 5, 2026

3 Sailings

Nov 7 - Dec 5, 2026

Published prices from

$839

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*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+9 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

A stunning view of Santa Cruz de la Palma's black sand beach, with gentle waves from the Atlantic Ocean, a colorful town, and green, volcanic mountains in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

28-night Trans-Atlantic Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Nafplion (Nauplia)
Crete
Valletta
Trapani
+11 more

Aboard

Silver Spirit

From

Piraeus (Athens), Greece

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 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
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

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

14-night Caribbean: Aruba & Curacao Cruise From Boston, Massachusetts

Boston
St. Thomas (Charlotte Amalie)
Castries
St. George's
Willemstad
+4 more

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

Published prices from

$869

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

6-night Southern Caribbean Cruise From Cartagena, Colombia

Cartagena (Colombia)
Oranjestad
Willemstad
Colon (Panama)

Aboard

Grandeur of the Seas

From

Cartagena, Colombia

3 Sailings

Nov 8, 2026 - Apr 23, 2028

3 Sailings

Nov 8, 2026 - Apr 23, 2028

Published prices from

$1,079

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
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,442

per person*

taxes & fees included

    • Showing results 1 - 24 of 716

*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.