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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.

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

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

14-night Eastern Caribbean Adventurer Cruise

Port Canaveral

Grand Turk

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

+3 more

Aboard

Sky Princess

From

Port Canaveral, Florida

5 Sailings

Nov 30, 2025 - Feb 22, 2026

5 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$2,723

per person*

taxes & fees included

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

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

6-night Eastern Caribbean With Turks & Caicos Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

4 Sailings

Dec 8, 2025 - Feb 16, 2026

4 Sailings

Dec 8, 2025 - Feb 16, 2026

Published prices from

$1,109

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

14-night Eastern Caribbean Adventurer Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

8 Sailings

May 17 - Sep 6, 2026

8 Sailings

May 17 - Sep 6, 2026

Published prices from

$2,220

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

12-night Southern Caribbean Islander Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Published prices from

$1,789

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

6-night Eastern Caribbean with Turks & Caicos Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

May 11, 2026

1 Sailing

May 11, 2026

Published prices from

$1,096

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern/Eastern Caribbean Adventurer Cruise

Grand Cayman (George Town)

+3 more

Aboard

Regal Princess

From

Fort Lauderdale, Florida

9 Sailings

Nov 8, 2026 - Feb 28, 2027

9 Sailings

Nov 8, 2026 - Feb 28, 2027

Published prices from

$2,263

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Turks & Caicos Cruise

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

Oct 10 - Oct 17, 2026

2 Sailings

Oct 10 - Oct 17, 2026

Published prices from

$1,149

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

6-night Eastern Caribbean With Turks & Caicos Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

Published prices from

$1,816

per person*

taxes & fees included

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

8-night Eastern Caribbean with Puerto Rico Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Published prices from

$2,509

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Eastern Caribbean With Turks & Caicos Cruise

Aboard

Regal Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 8, 2026 - Apr 4, 2027

10 Sailings

Nov 8, 2026 - Apr 4, 2027

Published prices from

$1,059

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

14-night Eastern/Western Caribbean Adventurer Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

13 Sailings

May 31 - Oct 4, 2026

13 Sailings

May 31 - Oct 4, 2026

Published prices from

$2,190

per person*

taxes & fees included

A sunny, idyllic beach scene in Amber Cove, Dominican Republic, with a small boat and paddle resting under a palm tree beside the turquoise ocean and a clear blue sky.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

7-night Eastern Caribbean Cruise with Turks & Caicos

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

Sep 20, 2026

1 Sailing

Sep 20, 2026

Published prices from

$1,186

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

3-night Maiden Caribbean With Princess Cays Crusie

Ft. Lauderdale

Princess Cays®

Nassau

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 7, 2025

1 Sailing

Nov 7, 2025

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

6-night Eastern Caribbean Cruise With Turks & Caicos

Aboard

Sky Princess

From

Port Canaveral, Florida

9 Sailings

Jan 19, 2026 - Mar 1, 2027

9 Sailings

Jan 19, 2026 - Mar 1, 2027

Published prices from

$1,045

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

14-night Eastern Caribbean Adventurer Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

2 Sailings

Dec 22 - Dec 28, 2025

2 Sailings

Dec 22 - Dec 28, 2025

Published prices from

$3,028

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

7-night Eastern Caribbean with Turks & Caicos Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

7 Sailings

May 17 - Oct 11, 2026

7 Sailings

May 17 - Oct 11, 2026

Published prices from

$1,221

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

13-night Southern Caribbean Islander Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 28, 2026

1 Sailing

Apr 28, 2026

Published prices from

$1,929

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Caribbean Eastern Adventurer Cruise

St. Maarten (Philipsburg)

+3 more

Aboard

Regal Princess

From

Fort Lauderdale, Florida

8 Sailings

Nov 22, 2026 - Feb 20, 2027

8 Sailings

Nov 22, 2026 - Feb 20, 2027

Published prices from

$2,397

per person*

taxes & fees included