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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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43 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.

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

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

TCW EXCLUSIVE

14-night Caribbean Celebration Voyage

Miami

Grand Cayman (George Town)

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$4,599

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Exclusive Savings & Events with Oceania Club*+ 1 more offer

10-night Classic Canal & Tropics Voyage

Aboard

Insignia

From

Panama City, Panama

1 Sailing

Apr 4, 2026

1 Sailing

Apr 4, 2026

Published prices from

$3,299

per person*

taxes & fees included

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

TCW EXCLUSIVE

19-night Caribbean Tour De Force Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Jan 8, 2026

1 Sailing

Jan 8, 2026

Published prices from

$5,699

per person*

taxes & fees included

Modern Panama City skyline with skyscrapers.

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

TCW EXCLUSIVE

20-night Panama Canal Connoisseur Voyage

Aboard

Insignia

From

Tampa, Florida

1 Sailing

Mar 25, 2026

1 Sailing

Mar 25, 2026

Published prices from

$5,799

per person*

taxes & fees included

Exclusive Savings & Events with Oceania Club*+ 1 more offer

10-night Canal & Caribbean Discovery Voyage

Aboard

Nautica

From

Panama City, Panama

1 Sailing

Jan 27, 2026

1 Sailing

Jan 27, 2026

Published prices from

$3,299

per person*

taxes & fees included

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

TCW EXCLUSIVE

14-night Holiday Havens Voyage

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 21, 2025

1 Sailing

Dec 21, 2025

Published prices from

$7,099

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Curated Caribbean Voyage

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$4,999

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Radiant Island Dawns Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Jan 15, 2026

1 Sailing

Jan 15, 2026

Published prices from

$3,499

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Tropical Island Rhythms Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Feb 26, 2026

1 Sailing

Feb 26, 2026

Published prices from

$3,599

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

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*+ 1 more offer

TCW EXCLUSIVE

12-night Exotic Caribbean Escape Voyage

Miami

Oranjestad

Willemstad

St. Vincent (Kingstown)

Castries

+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 1, 2027

1 Sailing

Feb 1, 2027

Published prices from

$3,799

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

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

TCW EXCLUSIVE

20-night Caribbean Kaleidoscope Voyage

Santo Tomas de Castilla

+10 more

Aboard

Nautica

From

Miami, Florida

1 Sailing

Jan 17, 2026

1 Sailing

Jan 17, 2026

Published prices from

$5,999

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Azure Caribbean Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Jan 5, 2026

1 Sailing

Jan 5, 2026

Published prices from

$3,499

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*+ 1 more offer

TCW EXCLUSIVE

13-night Bountiful Caribbean Voyage

Miami

Grand Cayman (George Town)

Aboard

Allura

From

Miami, Florida

1 Sailing

Jan 7, 2027

1 Sailing

Jan 7, 2027

Published prices from

$4,999

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Sunkissed Caribbean Shores Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Dec 7, 2025

1 Sailing

Dec 7, 2025

Published prices from

$2,499

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.

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

TCW EXCLUSIVE

28-night Antilles & Atlantic Gems Voyage

St. Vincent (Kingstown)

+9 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Mar 9, 2026

1 Sailing

Mar 9, 2026

Published prices from

$11,199

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

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

TCW EXCLUSIVE

36-night Caribbean To Cape Horn Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$9,999

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*+ 2 more offers

TCW EXCLUSIVE

12-night Dutch Isles Delights Voyage

St. Vincent (Kingstown)

+3 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Mar 9, 2026

1 Sailing

Mar 9, 2026

Published prices from

$5,849

per person*

taxes & fees included

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.

Exclusive Savings & Events with Oceania Club*

10-night Panama To Caribbean Joy Voyage

Aboard

Marina

From

Panama City, Panama

1 Sailing

Jan 15, 2027

1 Sailing

Jan 15, 2027

Published prices from

$2,999

per person*

taxes & fees included

A scenic panorama of the coastal city of Manta, Ecuador, with a densely packed urban area surrounded by lush green hills under a dramatic cloudy sky.

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

TCW EXCLUSIVE

15-night Antilles To Andes Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$4,099

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

31-night Island & Amazon Immersion Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Jan 15, 2026

1 Sailing

Jan 15, 2026

Published prices from

$8,099

per person*

taxes & fees included

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.

25-night Canada & Caribbean Isles Voyage

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

$11,299

per person*

taxes & fees included

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*+ 1 more offer

TCW EXCLUSIVE

14-night Dutchman's Caribbean Voyage

Miami

Grand Cayman (George Town)

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$4,899

per person*

taxes & fees included

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

TCW EXCLUSIVE

19-night Caribbean Spectrum Voyage

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$6,499

per person*

taxes & fees included

A white colonial-style cathedral with a bell tower and wooden doors is visible under a clear blue sky, likely in Santa Marta, Colombia.

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

TCW EXCLUSIVE

20-night Panama Canal & Caribbean Voyage

Santo Tomas de Castilla

+11 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Jan 5, 2027

1 Sailing

Jan 5, 2027

Published prices from

$6,199

per person*

taxes & fees included