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

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412 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

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

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
MSC Cruises logo

16 nights South Caribbean From Florence/Pisa (Livorno), Italy

Florence/Pisa (Livorno)
Provence (Marseille)
Barcelona (Tarragona)
Tangier
St. John's
+4 more

Aboard

MSC Opera

From

Florence/Pisa (Livorno), Italy

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$1,159

per person*

taxes & fees included

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

19 nights South Caribbean From Genoa, Italy

Genoa
Provence (Marseille)
Barcelona (Tarragona)
Gibraltar
Tangier
+7 more

Aboard

MSC Opera

From

Genoa, Italy

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

16 nights South Caribbean From Genoa, Italy

Genoa
Provence (Marseille)
Barcelona (Tarragona)
Gibraltar
Tangier
+5 more

Aboard

MSC Opera

From

Genoa, Italy

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$949

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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+6 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Into Caribbean Exploration & Island Delights From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$6,750

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
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 picturesque white sand beach in La Romana, Dominican Republic, with a distinctive black and white striped lighthouse and a wooden pier extending over the clear turquoise water. "
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

19 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Gibraltar
Tangier
St. John's
+7 more

Aboard

MSC Opera

From

Marseille, Provence, France

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$1,459

per person*

taxes & fees included

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

15 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Gibraltar
Tangier
St. John's
+4 more

Aboard

MSC Opera

From

Marseille, Provence, France

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$656

per person*

taxes & fees included

"A picturesque white sand beach in La Romana, Dominican Republic, with a distinctive black and white striped lighthouse and a wooden pier extending over the clear turquoise water. "
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

14 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Gibraltar
Tangier
St. John's
Philipsburg
+3 more

Aboard

MSC Opera

From

Tarragona, Spain

1 Sailing

Nov 2, 2026

1 Sailing

Nov 2, 2026

Published prices from

$852

per person*

taxes & fees included

A scenic panoramic shot from the top of the Rock of Gibraltar, overlooking the city, marina, and the Mediterranean Sea under a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

17 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Gibraltar
Tangier
St. John's
Philipsburg
+5 more

Aboard

MSC Opera

From

Tarragona, Spain

1 Sailing

Nov 2, 2026

1 Sailing

Nov 2, 2026

Published prices from

$1,344

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

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-night St. Thomas & St. Kitts Cruise From Port Canaveral, Florida

Port Canaveral
Puerto Plata
St. Thomas (Charlotte Amalie)
Basseterre

Aboard

Celebrity Apex

From

Port Canaveral, Florida

11 Sailings

Nov 7, 2026 - Apr 10, 2027

11 Sailings

Nov 7, 2026 - Apr 10, 2027

Published prices from

$1,169

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

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

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

8-night Eastern Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Basseterre
St. Maarten (Philipsburg)
San Juan
Grand Turk

Aboard

Adventure of the Seas

From

Fort Lauderdale, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$724

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
Silversea logo

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+3 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$6,300

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

Boats on a canal in Fort Lauderdale.
Princess Cruises logo

10-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. John's
St. Maarten (Philipsburg)
Dominica
Basseterre
+2 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 8 - Nov 18, 2026

2 Sailings

Nov 8 - Nov 18, 2026

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,108

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

12-night Caribbean Cruise: Dominican Republic & St. Thomas From New York City, New York

New York City
Puerto Plata
San Juan
Basseterre
Roadtown
+3 more

Aboard

Norwegian Bliss

From

New York City, New York

7 Sailings

Nov 9, 2026 - Mar 1, 2027

7 Sailings

Nov 9, 2026 - Mar 1, 2027

Published prices from

$1,119

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

$1,669

per person*

taxes & fees included

    • Showing results 1 - 24 of 412

*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.