The Cruise Web logo - 32 Years in Business

Our expert consultants and customer service teams are standing by to help with all of your cruising needs.

Explore with us

FacebookTwitterInstagramPinterestyoutube

Follow us for the latest cruise and travel news, including our best vacation deals.

Subscribe

Cruise Deals - delivered to your inbox

Five cruise ships in the port with very blue water surrounding them
Five cruise ships in the port with very blue water surrounding them

Destinations

Alaska

Asia

Australia/New Zealand

Canada/New England

Caribbean

Europe

Hawaii

Bahamas

All Destinations

Departure Ports

Baltimore

Galveston

New Orleans

Miami

Port Canaveral

All Departure Ports

Cruise Lines

Carnival Cruise Line

Celebrity Cruises

Holland America Line

Norwegian Cruise Line

Princess Cruises

Royal Caribbean Int'l

All Cruise Lines

Deals

Family Deals

Holiday Deals

Military Deals

Last Minute Deals

2026 Deals

Land Vacations

Cosmos Tours

Globus Tours

All Land Tours

All About Cruising

Articles

Experiences

All Ports

Contact Us

About Us

Already Booked

Gift Certificates

Future Cruise Credits

The Cruise Web, Inc.

8614 Westwood Center Drive
 Suite 800
 Tysons, VA 22182

Phone: 1-800-377-9383

International: +1 240-487-0155

Fax: 1-240-487-0154

BBB LogoCruise Lines International Association logo

© 1994 – 2026 The Cruise Web, Inc.

Terms and Conditions

Privacy Policy

Privacy Preferences

Do Not Sell or Share My Personal Information

4.9/5 ⭐Google 660+ Reviews | A+ Better Business Bureau

The Cruise Web logo - 32 Years in Business
DestinationsDeparture PortsCruise LinesDealsLand ToursFind Cruises
1-800-377-9383
The Cruise Web logo - 32 Years in Business
1-800-377-9383

Call

Offramp

30 Results

Taxes and fees included in all prices shown

Sort

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
Princess Cruises logo

8-night Southern Caribbean Islander Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Curacao
St. John's
St. Thomas (Charlotte Amalie)
+2 more

Aboard

Crown Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

11-night Southern Caribbean With Martinique Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
Basseterre
Fort de France
Bridgetown (Barbados)
+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+5 more

Aboard

Crown Princess

From

San Juan, Puerto Rico

12 Sailings

Dec 27, 2026 - Mar 14, 2027

12 Sailings

Dec 27, 2026 - Mar 14, 2027

Published prices from

$1,457

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean Cruise With Barbados From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+2 more

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

$667

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

5-night Eastern Caribbean With St. Kitts Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Dominica
St. George's

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 3, 2027

1 Sailing

Jan 3, 2027

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+2 more

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Puerto Rico Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
Pointe A Pitre
Dominica
+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

5 Sailings

Jan 29 - Mar 12, 2027

5 Sailings

Jan 29 - Mar 12, 2027

Published prices from

$1,489

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Islander Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Basseterre
St. John's
Castries
+5 more

Aboard

Regal Princess

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$1,224

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Adventurer Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Falmouth (Jamaica)
Oranjestad
Curacao
San Juan
+6 more

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$1,533

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

9-night Eastern Caribbean With St. Thomas Cruise From Port Canaveral, Florida

Port Canaveral
Grand Turk
Amber Cove
San Juan
St. Maarten (Philipsburg)
+2 more

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

$1,069

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

5-night Southern Caribbean With St. Lucia Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Dominica
Castries

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$618

per person*

taxes & fees included

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Barbados And St. Lucia Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Dominica
Castries
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$889

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Dominica
Castries
+5 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

14 Sailings

Nov 21, 2027 - Mar 12, 2028

14 Sailings

Nov 21, 2027 - Mar 12, 2028

Published prices from

$1,658

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

15-night Eastern Caribbean Adventurer Cruise From Miami, Florida

Miami
Amber Cove
San Juan
St. Maarten (Philipsburg)
Roadtown
+3 more

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

Published prices from

$1,683

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
Princess Cruises logo

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+2 more

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

$1,604

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
Princess Cruises logo

14-night Eastern/Western Caribbean Adventurer Cruise From Miami, Florida

Miami
Half Moon Cay
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Belize City
+4 more

Aboard

Regal Princess

From

Miami, Florida

10 Sailings

Dec 5, 2027 - Mar 26, 2028

10 Sailings

Dec 5, 2027 - Mar 26, 2028

Published prices from

$1,308

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Eastern Caribbean With St. Thomas Cruise From Miami, Florida

Miami
Half Moon Cay
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

Published prices from

$744

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Barbados And St. Lucia Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

8 Sailings

Dec 5, 2027 - Mar 12, 2028

8 Sailings

Dec 5, 2027 - Mar 12, 2028

Published prices from

$879

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Eastern Caribbean With St. Thomas Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 11, 2027 - Feb 12, 2028

3 Sailings

Dec 11, 2027 - Feb 12, 2028

Published prices from

$739

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Southern Caribbean With St. Lucia Cruise From Port Canaveral, Florida

Port Canaveral
San Juan
Basseterre
Castries
St. Maarten (Philipsburg)
+2 more

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

$1,324

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Adventurer Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+6 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

3 Sailings

Dec 12 - Dec 26, 2027

3 Sailings

Dec 12 - Dec 26, 2027

Published prices from

$1,793

per person*

taxes & fees included

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean With Martinique Holiday Cruise From Port Canaveral, Florida

Port Canaveral
Princess Cays®
Roadtown
St. Maarten (Philipsburg)
Fort de France
+6 more

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

Published prices from

$1,884

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With St. Lucia Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

1 Sailing

Dec 31, 2027

1 Sailing

Dec 31, 2027

Published prices from

$2,167

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

11-night Southern Caribbean With Barbados Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
Basseterre
Castries
Bridgetown (Barbados)
+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Jan 4 - Feb 15, 2028

3 Sailings

Jan 4 - Feb 15, 2028

Published prices from

$1,334

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-Eastern Caribbean Adventurer Cruise From Miami, Florida

Miami
Basseterre
San Juan
Amber Cove
Half Moon Cay
+3 more

Aboard

Regal Princess

From

Miami, Florida

5 Sailings

Jan 9 - Apr 2, 2028

5 Sailings

Jan 9 - Apr 2, 2028

Published prices from

$1,338

per person*

taxes & fees included

    • Showing results 1 - 24 of 30

*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.