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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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31 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

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

2 Sailings

Dec 19, 2025 - Feb 3, 2026

2 Sailings

Dec 19, 2025 - Feb 3, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

Rio de Janeiro panoramic with Sugarloaf Mountain and Guanabara Bay.

FREE Roundtrip First Class Airfare on Select Sailings*+ 1 more offer

14-night Season of Samba Cruise

Bridgetown (Barbados)

St. Vincent (Kingstown)

Aboard

Seven Seas Splendor

From

Bridgetown, Barbados

1 Sailing

Dec 3, 2025

1 Sailing

Dec 3, 2025

Published prices from

$15,899

per person*

taxes & fees included

FREE Dining, Onboard Activities & More*

10-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

Published prices from

$1,728

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

14-night Eastern and Southern Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 2026

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

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

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

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

TCW EXCLUSIVE

21-night Caribbean & South America Cruise

Ft. Lauderdale

San Juan

St. Thomas (Charlotte Amalie)

Gustavia

St. John's

+12 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

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 panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 11 - Feb 26, 2026

2 Sailings

Jan 11 - Feb 26, 2026

Published prices from

$5,500

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.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Southern Caribbean Cruise

Bridgetown (Barbados)

Trois Isles

St. Vincent (Kingstown)

Roseau

Gustavia

+3 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 12, 2026

1 Sailing

Feb 12, 2026

Published prices from

$5,400

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.

FREE Dining, Waterparks, Entertainment & More*+ 1 more offer

14-night Journeys - Southern Caribbean Cruise

Port Canaveral

St. Thomas (Charlotte Amalie)

Aboard

Carnival Venezia

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Published prices from

$1,334

per person*

taxes & fees included

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Caribbean Cruise

Bridgetown (Barbados)

St. Vincent (Kingstown)

St. George's

Trois Isles

St. Thomas (Charlotte Amalie)

+3 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Published prices from

$5,600

per person*

taxes & fees included

A scenic Caribbean bay near Kingstown, Saint Vincent and the Grenadines, with small boats anchored in the turquoise water and lush green hillsides with colorful houses.

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise

Ft. Lauderdale

San Juan

St. Thomas (Charlotte Amalie)

Gustavia

St. John's

+7 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$7,800

per person*

taxes & fees included

FREE Dining, Onboard Activities & More*

7-night Southern Caribbean Cruise

St. Vincent (Kingstown)

+2 more

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

18 Sailings

Nov 9, 2025 - Apr 12, 2026

18 Sailings

Nov 9, 2025 - Apr 12, 2026

Published prices from

$655

per person*

taxes & fees included

An aerial view of the vast Amazon River in Peru, meandering through a dense, green rainforest with a small floating lodge anchored along its banks.

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

19-night Amazon To Caribbean Gems Voyage

Bridgetown (Barbados)

Amazon River

Santarem

Parintins (Amazon River)

Manaus (Amazon River)

+9 more

Aboard

Insignia

From

Bridgetown, Barbados

1 Sailing

Jan 27, 2026

1 Sailing

Jan 27, 2026

Published prices from

$5,499

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*+ 2 more offers

TCW EXCLUSIVE

35-night Eastern Caribbean Cruise

London (Southampton)

Funchal (Madeira)

Bridgetown (Barbados)

Castries

St. George's

+9 more

Aboard

Queen Victoria

From

Southampton (London), England

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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 scenic view of Devil's Island, a small tropical island in French Guiana, completely covered by a dense forest of palm trees.

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

TCW EXCLUSIVE

30-night Caribbean Shores to Rio's Marvels Cruise

Aboard

Seven Seas Splendor

From

Miami, Florida

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

14-night Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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 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

10-night Best Of Southern Caribbean Cruise

Ft. Lauderdale

St. John's

Castries

Bridgetown (Barbados)

St. Vincent (Kingstown)

+2 more

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

2 Sailings

Jan 29 - Mar 12, 2027

2 Sailings

Jan 29 - Mar 12, 2027

Published prices from

$1,894

per person*

taxes & fees included

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.

Active & Retired Military Members Save up to $200*+ 1 more offer

11-night Southern Caribbean Intensive Cruise

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,694

per person*

taxes & fees included

7-night Southern Caribbean Cruise

St. Vincent (Kingstown)

+2 more

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

21 Sailings

Nov 1, 2026 - Apr 4, 2027

21 Sailings

Nov 1, 2026 - Apr 4, 2027

Published prices from

$666

per person*

taxes & fees included