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413 Results

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"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

$1,094

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

$953

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

36 Sailings

Nov 7, 2026 - Apr 15, 2028

36 Sailings

Nov 7, 2026 - Apr 15, 2028

Published prices from

$657

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

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

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

41 Sailings

Nov 8, 2026 - Apr 16, 2028

41 Sailings

Nov 8, 2026 - Apr 16, 2028

Published prices from

$567

per person*

taxes & fees included

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

$4,014

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

$1,749

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

$1,154

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

25-night Transatlantic Crossing and Eastern Caribbean Cruise From Southampton (London), England

London (Southampton)
New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
+2 more

Aboard

Queen Mary 2

From

Southampton (London), England

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$3,005

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*+ 3 more offers
TCW EXCLUSIVE
Cunard

18-night Transatlantic Crossing and Eastern Caribbean Cruise From Southampton (London), England

London (Southampton)
New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
+2 more

Aboard

Queen Mary 2

From

Southampton (London), England

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

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 Dutchman's Caribbean Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Falmouth (Jamaica)
Oranjestad
Willemstad
+5 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$5,649

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
MSC Cruises logo

10 nights East Caribbean From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Basseterre
Philipsburg
St. John's
+3 more

Aboard

MSC Poesia

From

Miami, Florida

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$1,069

per person*

taxes & fees included

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

21 nights East Caribbean From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Basseterre
Philipsburg
St. John's
+9 more

Aboard

MSC Poesia

From

Miami, Florida

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$2,435

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

22 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+10 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,369

per person*

taxes & fees included

A panoramic aerial shot of the arid landscape of Fuerteventura, Spain, with the town of Antigua visible in the foreground and the Atlantic Ocean in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

21 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
La Spezia
Provence (Marseille)
Barcelona (Tarragona)
+9 more

Aboard

MSC World Europa

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,261

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

28 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
La Spezia
Provence (Marseille)
Barcelona (Tarragona)
+12 more

Aboard

MSC World Europa

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

An aerial view of Kingston Beach, a residential suburb near Hobart, Tasmania, Australia. The image shows the curved white-sand beach and the adjacent neighborhood of houses and streets, bordering the calm, blue waters of the River Derwent estuary.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

18 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+9 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

An aerial view of Kingston Beach, a residential suburb near Hobart, Tasmania, Australia. The image shows the curved white-sand beach and the adjacent neighborhood of houses and streets, bordering the calm, blue waters of the River Derwent estuary.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

28 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+13 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,985

per person*

taxes & fees included

    • Showing results 1 - 24 of 413

*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.