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374 Results

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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.
Carnival Cruise Line Logo

8-night Eastern Caribbean Cruise From Miami, Florida

Miami
Half Moon Cay
San Juan
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)

Aboard

Carnival Magic

From

Miami, Florida

20 Sailings

Oct 31, 2026 - Mar 11, 2028

20 Sailings

Oct 31, 2026 - Mar 11, 2028

Two colorful striped beach chairs sit on the white sand beach of Great Stirrup Cay, Bahamas, facing the clear turquoise water under a bright blue sky with palm fronds overhead.
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay, Dominican Republic & Tortola From Miami, Florida

Miami
Puerto Plata
St. Thomas (Charlotte Amalie)
Roadtown
Great Stirrup Cay

Aboard

Norwegian Luna

From

Miami, Florida

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$609

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

A golden-hour shot of a sandy beach in Portimão, Portugal, with the clear water of the Atlantic Ocean gently washing over the sand and the large, jagged limestone rock formations of the Algarve coast lit by the sun.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

38-night Athens to Miami Grand Voyage From Piraeus (Athens), Greece

Athens (Piraeus)
Olympia
Sarande
Siracusa
Catania
+21 more

Aboard

Azamara Quest

From

Piraeus (Athens), Greece

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

7-night Eastern Caribbean Cruise From Port Canaveral, Florida

Port Canaveral
Celebration Key
San Juan
St. Thomas (Charlotte Amalie)

Aboard

Carnival Venezia

From

Port Canaveral, Florida

11 Sailings

Nov 1, 2026 - May 2, 2027

11 Sailings

Nov 1, 2026 - May 2, 2027

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.
50% Off + Kids Sail FREE + FREE Pre-Paid Tips*
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic From Port Canaveral, Florida

Port Canaveral
Puerto Plata
St. Thomas (Charlotte Amalie)
Roadtown
Great Stirrup Cay

Aboard

Norwegian Prima

From

Port Canaveral, Florida

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$509

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Eastern Caribbean & Perfect Day Cruise From Miami, Florida

Miami
Perfect Day at CocoCay
San Juan
St. Thomas (Charlotte Amalie)

Aboard

Allure of the Seas

From

Miami, Florida

4 Sailings

Nov 1, 2026 - Apr 11, 2027

4 Sailings

Nov 1, 2026 - Apr 11, 2027

Published prices from

$682

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Eastern Caribbean & Perfect Day Cruise From Port Canaveral, Florida

Port Canaveral
Perfect Day at CocoCay
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)

Aboard

Star of the Seas

From

Port Canaveral, Florida

29 Sailings

Nov 1, 2026 - Apr 16, 2028

29 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$1,123

per person*

taxes & fees included

Anaga Mountains landscape, Tenerife.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

14-night Transatlantic Cruise: Bahamas & Spain From Barcelona, Spain

Barcelona
Seville (Cadiz)
Santa Cruz de Tenerife
St. Thomas (Charlotte Amalie)
Great Stirrup Cay
+2 more

Aboard

Norwegian Epic

From

Barcelona, Spain

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$969

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*+ 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

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to 60% off 2nd Guest + Kids Sail Free*
Royal Caribbean logo

7-night Eastern Caribbean & Perfect Day Cruise From Miami, Florida

Miami
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
Perfect Day at CocoCay

Aboard

Icon of the Seas

From

Miami, Florida

12 Sailings

Nov 7, 2026 - Apr 10, 2027

12 Sailings

Nov 7, 2026 - Apr 10, 2027

Published prices from

$1,399

per person*

taxes & fees included

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.
Carnival Cruise Line Logo

7-night Eastern Caribbean Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
San Juan
Celebration Key

Aboard

Carnival Celebration

From

Miami, Florida

52 Sailings

Nov 8, 2026 - Mar 26, 2028

52 Sailings

Nov 8, 2026 - Mar 26, 2028

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

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.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic From Miami, Florida

Miami
Puerto Plata
St. Thomas (Charlotte Amalie)
Roadtown
Great Stirrup Cay

Aboard

Norwegian Aqua

From

Miami, Florida

21 Sailings

Nov 8, 2026 - Mar 28, 2027

21 Sailings

Nov 8, 2026 - Mar 28, 2027

Published prices from

$439

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 Puerto Plata & St. Maarten Cruise From Miami, Florida

Miami
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
Puerto Plata

Aboard

Celebrity Xcel

From

Miami, Florida

3 Sailings

Nov 8, 2026 - Mar 14, 2027

3 Sailings

Nov 8, 2026 - Mar 14, 2027

Published prices from

$1,143

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

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

$1,104

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

$2,839

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

    • Showing results 1 - 24 of 374

*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.