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362 Results

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Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to 60% off 2nd Guest + Kids Sail Free*
Royal Caribbean logo

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

Port Canaveral
St. Croix
St. Thomas (Charlotte Amalie)
San Juan
Perfect Day at CocoCay

Aboard

Adventure of the Seas

From

Port Canaveral, Florida

1 Sailing

Oct 16, 2026

1 Sailing

Oct 16, 2026

Published prices from

$975

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Save up to 55% on Select Sailings*
Carnival Cruise Line Logo

8-night Eastern Caribbean Cruise From Port Canaveral, Florida

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

Aboard

Carnival Vista

From

Port Canaveral, Florida

10 Sailings

Oct 17, 2026 - Dec 31, 2027

10 Sailings

Oct 17, 2026 - Dec 31, 2027

Published prices from

$638

per person*

taxes & fees included

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

3 Sailings

Oct 17 - Oct 31, 2026

3 Sailings

Oct 17 - Oct 31, 2026

Published prices from

$509

per person*

taxes & fees included

Historic buildings in Galveston, Texas.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

14-night Carnival Journeys Cruise - Eastern Caribbean From Galveston, Texas

Galveston
Key West
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
+5 more

Aboard

Carnival Dream

From

Galveston, Texas

2 Sailings

Oct 17, 2026 - Jan 16, 2027

2 Sailings

Oct 17, 2026 - Jan 16, 2027

Published prices from

$1,489

per person*

taxes & fees included

A beautiful autumn landscape in Saguenay with a river flowing under a bridge, surrounded by hillsides adorned with houses and vibrant yellow, orange, and red fall foliage.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

25-night Canada & Caribbean Isles Voyage From Montreal, Quebec

Montreal
Quebec City
Saguenay
Baie-Comeau (Comeau Bay)
Sept-Iles
+16 more

Aboard

Vista

From

Montreal, Quebec

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$11,949

per person*

taxes & fees included

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

54 Sailings

Oct 18, 2026 - Mar 26, 2028

54 Sailings

Oct 18, 2026 - Mar 26, 2028

Published prices from

$647

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 50% off + Kids Sail Free*
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

2 Sailings

Oct 18 - Nov 1, 2026

2 Sailings

Oct 18 - Nov 1, 2026

Published prices from

$559

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

14-night Journeys - Southern Caribbean Cruise From Port Canaveral, Florida

Port Canaveral
St. Thomas (Charlotte Amalie)
St. John's
Fort de France
St. George's
+5 more

Aboard

Carnival Venezia

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Published prices from

$1,167

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
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

31 Sailings

Oct 18, 2026 - Apr 16, 2028

31 Sailings

Oct 18, 2026 - Apr 16, 2028

Published prices from

$1,216

per person*

taxes & fees included

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

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

13 Sailings

Oct 24, 2026 - Apr 10, 2027

13 Sailings

Oct 24, 2026 - Apr 10, 2027

Published prices from

$1,375

per person*

taxes & fees included

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

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

Published prices from

$518

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

Published prices from

$1,789

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

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

$1,054

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

$1,694

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

Published prices from

$525

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*+ 2 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

$776

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

$869

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

$1,181

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*+ 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

$1,069

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

$539

per person*

taxes & fees included

    • Showing results 1 - 24 of 362

*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.