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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*+ 2 more offers

14-night Eastern/Western Caribbean Adventurer Cruise

Princess Cays®

Aboard

Regal Princess

From

Fort Lauderdale, Florida

22 Sailings

May 9, 2026 - Mar 20, 2027

22 Sailings

May 9, 2026 - Mar 20, 2027

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*+ 2 more offers

7-night Eastern Caribbean with St. Thomas Cruise

Princess Cays®

St. Thomas (Charlotte Amalie)

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

May 23 - Aug 15, 2026

2 Sailings

May 23 - Aug 15, 2026

A scenic view of Princess Cays, Bahamas, featuring a row of colorful cabanas with thatched roofs, surrounded by swaying palm trees on a white-sand beach.

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

7-night Eastern Caribbean Cruise with St. Thomas

Princess Cays®

St. Thomas (Charlotte Amalie)

Aboard

Regal Princess

From

Fort Lauderdale, Florida

1 Sailing

Jul 18, 2026

1 Sailing

Jul 18, 2026

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

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

8-night Southern Caribbean Islander Holiday Cruise

St. Thomas (Charlotte Amalie)

Aboard

Crown Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Boats on a canal in Fort Lauderdale.

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

11-night Southern Caribbean With Martinique Holiday Cruise

St. Thomas (Charlotte Amalie)

Bridgetown (Barbados)

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

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.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 1 more offer

14-night Southern Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

12 Sailings

Dec 27, 2026 - Mar 14, 2027

12 Sailings

Dec 27, 2026 - Mar 14, 2027

Rocky beach and palm trees in Barbados.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 1 more offer

7-night Southern Caribbean Cruise With Barbados

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

13 Sailings

Dec 27, 2026 - Mar 21, 2027

13 Sailings

Dec 27, 2026 - Mar 21, 2027

Published prices from

$1,161

per person*

taxes & fees included

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

5-night Eastern Caribbean With St. Kitts Cruise

St. Thomas (Charlotte Amalie)

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 3, 2027

1 Sailing

Jan 3, 2027

Rocky beach and palm trees in Barbados.

7-night Southern Caribbean With St. Lucia Cruise

Bridgetown (Barbados)

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

Bridgetown, Barbados

6 Sailings

Jan 8 - Mar 19, 2027

6 Sailings

Jan 8 - Mar 19, 2027

Rocky beach and palm trees in Barbados.

7-night Southern Caribbean With Puerto Rico Cruise

Bridgetown (Barbados)

St. Thomas (Charlotte Amalie)

Aboard

Crown Princess

From

Bridgetown, Barbados

5 Sailings

Jan 29 - Mar 12, 2027

5 Sailings

Jan 29 - Mar 12, 2027

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*

14-night Southern Caribbean Islander Cruise

St. Thomas (Charlotte Amalie)

Aboard

Regal Princess

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Up to $500 FREE Onboard Credit*

14-night Southern Caribbean Adventurer Holiday Cruise

Falmouth (Jamaica)

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Cupecoy Beach with white resort buildings, St. Maarten.

9-night Eastern Caribbean With St. Thomas Cruise

St. Maarten (Philipsburg)

Aboard

Star Princess

From

Port Canaveral, Florida

3 Sailings

Nov 14, 2027 - Mar 29, 2028

3 Sailings

Nov 14, 2027 - Mar 29, 2028

Published prices from

$1,724

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.

5-night Southern Caribbean With St. Lucia Holiday Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

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

7-night Southern Caribbean With Barbados And St. Lucia Holiday Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

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

14-night Southern Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

14 Sailings

Nov 21, 2027 - Mar 12, 2028

14 Sailings

Nov 21, 2027 - Mar 12, 2028

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

15-night Eastern Caribbean Adventurer Cruise

St. Maarten (Philipsburg)

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

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.

7-night Southern Caribbean With St. Lucia Cruise

Bridgetown (Barbados)

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

Bridgetown, Barbados

6 Sailings

Dec 3, 2027 - Mar 10, 2028

6 Sailings

Dec 3, 2027 - Mar 10, 2028

Published prices from

$1,924

per person*

taxes & fees included

A stunning underwater view of two sea turtles swimming gracefully in the crystal-clear turquoise waters of the Bahamas, with a small island visible in the background.

Up to $500 FREE Onboard Credit*

14-night Eastern/Western Caribbean Adventurer Cruise

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Regal Princess

From

Miami, Florida

10 Sailings

Dec 5, 2027 - Mar 26, 2028

10 Sailings

Dec 5, 2027 - Mar 26, 2028

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

Up to $500 FREE Onboard Credit*

7-night Eastern Caribbean With St. Thomas Cruise

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Regal Princess

From

Miami, Florida

6 Sailings

Dec 5, 2027 - Apr 9, 2028

6 Sailings

Dec 5, 2027 - Apr 9, 2028

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

7-night Southern Caribbean With Barbados And St. Lucia Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

8 Sailings

Dec 5, 2027 - Mar 12, 2028

8 Sailings

Dec 5, 2027 - Mar 12, 2028

A scenic view of Princess Cays, Bahamas, featuring a row of colorful cabanas with thatched roofs, surrounded by swaying palm trees on a white-sand beach.

Up to $500 FREE Onboard Credit*

7-night Eastern Caribbean With St. Thomas Cruise

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

4 Sailings

Dec 11, 2027 - Mar 4, 2028

4 Sailings

Dec 11, 2027 - Mar 4, 2028

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.

10-night Southern Caribbean With St. Lucia Cruise

Aboard

Star Princess

From

Port Canaveral, Florida

2 Sailings

Dec 12, 2027 - Mar 19, 2028

2 Sailings

Dec 12, 2027 - Mar 19, 2028

Published prices from

$1,959

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

14-night Southern Caribbean Adventurer Holiday Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

3 Sailings

Dec 12 - Dec 26, 2027

3 Sailings

Dec 12 - Dec 26, 2027

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.

14-night Southern Caribbean With Martinique Holiday Cruise

Celebration Key

St. Maarten (Philipsburg)

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

*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.