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31 Results

Taxes and fees included in all prices shown

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Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

13-night Caribbean Cruise: Aruba, Bahamas & Bermuda From New York City, New York

New York City
Royal Naval Dockyard
San Juan
St. Thomas (Charlotte Amalie)
Roadtown
+6 more

Aboard

Norwegian Sun

From

New York City, New York

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Caribbean Enchantment Voyage From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Roadtown
St. John's
Basseterre
+6 more

Aboard

Vista

From

New York City, New York

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$5,599

per person*

taxes & fees included

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

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

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+8 more

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

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*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

30-night Legendary Amazon Explorer Cruise From New York City, New York

New York City
Ft. Lauderdale
St. Maarten (Philipsburg)
Fort de France
Bridgetown (Barbados)
+12 more

Aboard

Volendam

From

New York City, New York

1 Sailing

Nov 22, 2026

1 Sailing

Nov 22, 2026

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

14-night Caribbean Celebration Cruise From New York City, New York

New York City
Roadtown
St. Maarten (Philipsburg)
Bridgetown (Barbados)
Castries
+3 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$1,899

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

23-night Transatlantic Crossing and Caribbean Celebration Cruise From New York City, New York

New York City
Roadtown
St. Maarten (Philipsburg)
Bridgetown (Barbados)
Castries
+4 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$3,389

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
Cunard

17-night 2027 World Voyage Segment: New York To Los Angeles From New York City, New York

New York City
Oranjestad
Panama Canal
Acajutla
Puerto Vallarta
+2 more

Aboard

Queen Victoria

From

New York City, New York

1 Sailing

Jan 19, 2027

1 Sailing

Jan 19, 2027

Published prices from

$2,959

per person*

taxes & fees included

Waterfall and rainbow in Hilo, Hawaii.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

100-night 2027 World Voyage From New York City, New York

New York City
Oranjestad
Panama Canal
Acajutla
Puerto Vallarta
+29 more

Aboard

Queen Victoria

From

New York City, New York

1 Sailing

Jan 19, 2027

1 Sailing

Jan 19, 2027

Published prices from

$25,569

per person*

taxes & fees included

Hollywood sign on hills of Los Angeles.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

35-night 2027 World Voyage Segment: New York To Sydney From New York City, New York

New York City
Oranjestad
Panama Canal
Acajutla
Puerto Vallarta
+8 more

Aboard

Queen Victoria

From

New York City, New York

1 Sailing

Jan 19, 2027

1 Sailing

Jan 19, 2027

Published prices from

$9,409

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
Azamara logo

17-night Bermuda & Eastern Caribbean Cruise: Sint Maarten, Antigua & Tobago From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+9 more

Aboard

Azamara Quest

From

New York City, New York

1 Sailing

Oct 28, 2027

1 Sailing

Oct 28, 2027

Published prices from

$4,129

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
Azamara logo

24-night Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+13 more

Aboard

Azamara Quest

From

New York City, New York

1 Sailing

Oct 28, 2027

1 Sailing

Oct 28, 2027

Published prices from

$6,129

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

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

New York City
St. Thomas (Charlotte Amalie)
St. Croix
Oranjestad
Curacao
+3 more

Aboard

Carnival Firenze

From

New York City, New York

1 Sailing

Nov 2, 2027

1 Sailing

Nov 2, 2027

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

10-night Caribbean from New York to San Juan Cruise: Bermuda & Barbados From New York City, New York

New York City
Royal Naval Dockyard
Roadtown
Basseterre
Bridgetown (Barbados)
+5 more

Aboard

Norwegian Prima

From

New York City, New York

1 Sailing

Nov 3, 2027

1 Sailing

Nov 3, 2027

Published prices from

$1,789

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 Sun-Kissed Soiree Cruise From New York City, New York

New York City
Nassau
Bahamian Waters
Cabo Rojo
Willemstad
+6 more

Aboard

Seven Seas Grandeur

From

New York City, New York

1 Sailing

Nov 4, 2027

1 Sailing

Nov 4, 2027

Published prices from

$8,799

per person*

taxes & fees included

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

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

New York City
St. Thomas (Charlotte Amalie)
Basseterre
St. John's
Castries
+5 more

Aboard

Regal Princess

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$1,224

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
Oceania Cruises

15-night Broadway To The Abc Islands Voyage From New York City, New York

New York City
Roadtown
St. John's
Basseterre
Kralendijk
+6 more

Aboard

Sirena

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$4,149

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
Cunard

13-night Eastern Caribbean Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Basseterre
Castries
Bridgetown (Barbados)
+3 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Nov 19, 2027

1 Sailing

Nov 19, 2027

Published prices from

$1,599

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

20-night Transatlantic & Caribbean Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Basseterre
Castries
Bridgetown (Barbados)
+4 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Nov 19, 2027

1 Sailing

Nov 19, 2027

Published prices from

$2,779

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

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

New York City
San Juan
Oranjestad
Curacao
Ft. Lauderdale

Aboard

Coral Princess

From

New York City, New York

1 Sailing

Nov 26, 2027

1 Sailing

Nov 26, 2027

Published prices from

$1,359

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

13-night Caribbean Cruise From New York City, New York

New York City
Basseterre
Castries
Bridgetown (Barbados)
Roseau
+2 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Dec 21, 2027

1 Sailing

Dec 21, 2027

Published prices from

$2,399

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

21-night Transatlantic & Caribbean Cruise From New York City, New York

New York City
Basseterre
Castries
Bridgetown (Barbados)
Roseau
+3 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Dec 21, 2027

1 Sailing

Dec 21, 2027

Published prices from

$3,169

per person*

taxes & fees included

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

20-night Transatlantic Crossing Cruise From New York City, New York

New York City
Basseterre
Castries
Bridgetown (Barbados)
Roseau
+3 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$3,079

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

12-night Eastern Caribbean Cruise From New York City, New York

New York City
Basseterre
Castries
Bridgetown (Barbados)
Roseau
+2 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$1,999

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Silversea logo

13-night Southern Caribbean Featuring St. Barts & Aruba Cruise From New York City, New York

New York City
Hamilton
Virgin Gorda
Gustavia
Willemstad
+3 more

Aboard

Silver Spirit

From

New York City, New York

1 Sailing

Oct 21, 2028

1 Sailing

Oct 21, 2028

Published prices from

$6,250

per person*

taxes & fees included

    • Showing results 1 - 24 of 31

*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.