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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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18 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.

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

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

Cupecoy Beach with white resort buildings, St. Maarten.

Exclusive Savings & Events with Oceania Club*

20-night Sju to Mia Voyage

San Juan

Gustavia

St. Maarten (Philipsburg)

Basseterre

St. John's

+10 more

Aboard

Allura

From

San Juan, Puerto Rico

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$7,799

per person*

taxes & fees included

27-night East Coast Escapade Voyage

Montreal

Quebec City

Saguenay

Baie-Comeau (Comeau Bay)

Havre-Saint-Pierre

+16 more

Aboard

Sirena

From

Montreal, Quebec

1 Sailing

Oct 25, 2027

1 Sailing

Oct 25, 2027

Published prices from

$8,799

per person*

taxes & fees included

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

TCW EXCLUSIVE

15-night Broadway To The Abc Islands Voyage

Aboard

Sirena

From

New York, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$4,199

per person*

taxes & fees included

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

Up to $500 FREE Onboard Credit*

TCW EXCLUSIVE

31-night Loving The Island Life Voyage

Aboard

Sirena

From

Miami, Florida

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$8,299

per person*

taxes & fees included

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

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

Modern Panama City skyline with skyscrapers.

Exclusive Savings & Events with Oceania Club*

11-night Classic Caribbean Canal Voyage

Aboard

Nautica

From

Panama City, Panama

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

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

A breathtaking view of the Los Morrillos Lighthouse and the rugged coastline of Cabo Rojo, Puerto Rico, with dramatic cliffs and turquoise water.

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

TCW EXCLUSIVE

12-night Dutch & French Flair Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Mar 7, 2028

1 Sailing

Mar 7, 2028

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*+ 1 more offer

TCW EXCLUSIVE

14-night Festive Caribbean Frolic Voyage

Aboard

Sirena

From

Miami, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

Published prices from

$4,399

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

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 Curated Caribbean Voyage

Aboard

Marina

From

Miami, Florida

1 Sailing

Jan 26, 2028

1 Sailing

Jan 26, 2028

Published prices from

$3,799

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

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*+ 1 more offer

TCW EXCLUSIVE

12-night Radiant Island Retreats Voyage

Miami

Grand Cayman (George Town)

Aboard

Allura

From

Miami, Florida

1 Sailing

Feb 27, 2027

1 Sailing

Feb 27, 2027

Published prices from

$4,599

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Caribbean Carousel Voyage

Aboard

Sirena

From

Miami, Florida

1 Sailing

Nov 28, 2027

1 Sailing

Nov 28, 2027

Published prices from

$3,399

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