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4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

Destinations Departure Ports Cruise Lines Deals Land Tours Find Cruises

1-800-377-9383

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34 Results

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*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.

Calshot Castle, a historic Tudor fort near Southampton, England.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

20-night Transatlantic Crossing And Caribbean Celebration Cruise

New York City

St. Thomas (Charlotte Amalie)

Basseterre

St. Maarten (Philipsburg)

Roadtown

+2 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

Statue of Liberty and Manhattan skyline.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

9-night Eastern Caribbean Cruise

Aboard

Carnival Venezia

From

New York, New York

1 Sailing

Jun 1, 2026

1 Sailing

Jun 1, 2026

Published prices from

$839

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

12-night Caribbean Celebration Cruise

New York City

St. Thomas (Charlotte Amalie)

Basseterre

St. Maarten (Philipsburg)

Roadtown

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean Islander Cruise

New York City

St. Maarten (Philipsburg)

Aboard

Majestic Princess

From

New York, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$2,299

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 more offers

TCW EXCLUSIVE

18-night Transatlantic Crossing and Eastern Caribbean Cruise

New York City

St. Thomas (Charlotte Amalie)

Basseterre

English Harbour

St. Maarten (Philipsburg)

+2 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$2,929

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

15-night Auburn Sunsets, Turquoise Seas Cruise

Bridgetown (Barbados)

+7 more

Aboard

Seven Seas Splendor

From

New York, New York

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 2025

Published prices from

$13,299

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

12-night Carnival Journeys Cruise - Southern Caribbean

New York City

St. Thomas (Charlotte Amalie)

Aboard

Carnival Venezia

From

New York, New York

1 Sailing

Nov 8, 2025

1 Sailing

Nov 8, 2025

Published prices from

$769

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

19-night Transatlantic Crossing And Eastern Caribbean Cruise

New York City

St. Maarten (Philipsburg)

Roseau

Bridgetown (Barbados)

Castries

+3 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Nov 26, 2025

1 Sailing

Nov 26, 2025

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

12-night Eastern Caribbean Cruise

New York City

St. Maarten (Philipsburg)

Roseau

Bridgetown (Barbados)

Castries

+2 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Nov 26, 2025

1 Sailing

Nov 26, 2025

Published prices from

$2,979

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 6 more offers

TCW EXCLUSIVE

12-night Caribbean Cruise: Barbados & Antigua

New York City

Basseterre

Castries

Bridgetown (Barbados)

St. Maarten (Philipsburg)

+2 more

Aboard

Norwegian Breakaway

From

New York, New York

3 Sailings

Nov 30, 2025 - Feb 22, 2026

3 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$899

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 6 more offers

TCW EXCLUSIVE

12-night Caribbean Cruise: Dominican Republic & St. Thomas

Aboard

Norwegian Bliss

From

New York, New York

7 Sailings

Nov 9, 2026 - Mar 1, 2027

7 Sailings

Nov 9, 2026 - Mar 1, 2027

Published prices from

$1,730

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 more offers

TCW EXCLUSIVE

14-night Caribbean Celebration Cruise

New York City

Roadtown

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Castries

+3 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$3,749

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Caribbean Islander Cruise

New York City

St. Maarten (Philipsburg)

Aboard

Enchanted Princess

From

New York, New York

1 Sailing

Nov 1, 2025

1 Sailing

Nov 1, 2025

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.

Up to $500 FREE Onboard Credit*+ 6 more offers

TCW EXCLUSIVE

10-night Caribbean Cruise: Dominican Republic & St. Thomas

New York City

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

Roadtown

+2 more

Aboard

Norwegian Escape

From

New York, New York

1 Sailing

Aug 19, 2026

1 Sailing

Aug 19, 2026

Published prices from

$2,190

per person*

taxes & fees included

An aerial view of the vast Amazon River in Peru, meandering through a dense, green rainforest with a small floating lodge anchored along its banks.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

30-night Legendary Amazon Explorer Cruise

New York City

Ft. Lauderdale

St. Maarten (Philipsburg)

Fort de France

Bridgetown (Barbados)

+12 more

Aboard

Volendam

From

New York, New York

1 Sailing

Nov 22, 2026

1 Sailing

Nov 22, 2026

Published prices from

$6,854

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*+ 4 more offers

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise

New York City

St. Thomas (Charlotte Amalie)

Basseterre

English Harbour

St. Maarten (Philipsburg)

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,779

per person*

taxes & fees included

A stunning underwater view of two sea turtles swimming gracefully in the crystal-clear turquoise waters of the Bahamas, with a small island visible in the background.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

8-night Eastern Caribbean Cruise

Aboard

Carnival Venezia

From

New York, New York

8 Sailings

Jun 10 - Sep 2, 2026

8 Sailings

Jun 10 - Sep 2, 2026

Published prices from

$779

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*+ 6 more offers

TCW EXCLUSIVE

13-night Caribbean Cruise: Aruba, Bahamas & Bermuda

New York City

Royal Naval Dockyard

San Juan

St. Thomas (Charlotte Amalie)

Roadtown

+6 more

Aboard

Norwegian Sun

From

New York, New York

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

Published prices from

$1,960

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

30-night Amazon Explorer Cruise

New York City

Ft. Lauderdale

St. Maarten (Philipsburg)

Castries

Bridgetown (Barbados)

+15 more

Aboard

Volendam

From

New York, New York

1 Sailing

Nov 21, 2025

1 Sailing

Nov 21, 2025

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

16-night Caribbean Voyage: New York, Bermuda & Barbados

New York City

Hamilton

St. Maarten (Philipsburg)

Roadtown

San Juan

+8 more

Aboard

Azamara Journey

From

New York, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$3,439

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*

TCW EXCLUSIVE

14-night Caribbean Enchantment Voyage

New York City

St. Thomas (Charlotte Amalie)

Aboard

Vista

From

New York, New York

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,999

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 more offers

TCW EXCLUSIVE

23-night Transatlantic Crossing and Caribbean Celebration Cruise

New York City

Roadtown

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Castries

+4 more

Aboard

Queen Mary 2

From

New York, New York

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$5,513

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*+ 6 more offers

TCW EXCLUSIVE

11-night Caribbean Cruise: Barbados & Antigua

New York City

Roadtown

Basseterre

St. Thomas (Charlotte Amalie)

San Juan

+2 more

Aboard

Norwegian Breakaway

From

New York, New York

1 Sailing

Dec 12, 2025

1 Sailing

Dec 12, 2025

Published prices from

$799

per person*

taxes & fees included

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Bermuda & Caribbean Voyage: New York, Bermuda & St. Maarten

New York City

Hamilton

St. Maarten (Philipsburg)

Roadtown

San Juan

Aboard

Azamara Journey

From

New York, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$1,809

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*+ 6 more offers

TCW EXCLUSIVE

11-night Caribbean Cruise: Dominican Republic & St. Thomas

New York City

Puerto Plata

San Juan

St. Maarten (Philipsburg)

Roadtown

+2 more

Aboard

Norwegian Breakaway

From

New York, New York

3 Sailings

Jan 12 - Feb 3, 2026

3 Sailings

Jan 12 - Feb 3, 2026

Published prices from

$780

per person*

taxes & fees included