The Cruise Web | Find Cruises Deals

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

+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.

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

5-night Caribbean Getaway With Grand Turk Cruise

Amber Cove

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$1,644

per person*

taxes & fees included

6-night Eastern Caribbean With Turks & Caicos Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

Published prices from

$1,446

per person*

taxes & fees included

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

14-night Eastern/Western Caribbean Adventurer Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

34 Sailings

Nov 29, 2025 - Mar 20, 2027

34 Sailings

Nov 29, 2025 - Mar 20, 2027

Published prices from

$2,438

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

8-night Eastern Caribbean With St. Thomas Cruise

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

Aboard

Sky Princess

From

Port Canaveral, Florida

3 Sailings

Dec 14, 2025 - Feb 8, 2026

3 Sailings

Dec 14, 2025 - Feb 8, 2026

Published prices from

$1,694

per person*

taxes & fees included

Puntarenas, Costa Rica tropical landscape with palm trees and mountains.

27-night Panama Canal and Caribbean Adventurer Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

Published prices from

$4,373

per person*

taxes & fees included

8-night Eastern Caribbean Cruise With St. Thomas

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

Aboard

Star Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 28 - Apr 5, 2026

2 Sailings

Mar 28 - Apr 5, 2026

Published prices from

$2,224

per person*

taxes & fees included

8-night Eastern Caribbean With Puerto Rico Cruise

Amber Cove

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Published prices from

$1,684

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.

10-night Eastern Caribbean With St. Kitts Holiday Cruise

Princess Cays®

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

Basseterre

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 17, 2025 - Dec 27, 2026

3 Sailings

Dec 17, 2025 - Dec 27, 2026

Published prices from

$2,039

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.

18-night Southern Caribbean Adventurer Cruise

Dominica

St. George's

Bridgetown (Barbados)

+10 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 29, 2026

1 Sailing

Mar 29, 2026

Published prices from

$2,958

per person*

taxes & fees included

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

14-night Caribbean South/East Adventurer Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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

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

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

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

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

6 Sailings

Nov 15, 2025 - Dec 19, 2026

6 Sailings

Nov 15, 2025 - Dec 19, 2026

Published prices from

$3,503

per person*

taxes & fees included

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

7-night Eastern Caribbean With Bahamas Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 22 - Dec 20, 2025

2 Sailings

Nov 22 - Dec 20, 2025

Published prices from

$1,676

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.

14-night Circle Caribbean Cruise

Dominica

Castries

Bridgetown (Barbados)

+5 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Jan 31, 2026

1 Sailing

Jan 31, 2026

Published prices from

$3,129

per person*

taxes & fees included

12-night Eastern Caribbean Adventurer Cruise

Princess Cays®

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

+2 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 22, 2026

1 Sailing

Mar 22, 2026

Published prices from

$2,478

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.

8-night Eastern Caribbean with St. Thomas Cruise

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

Aboard

Sky Princess

From

Port Canaveral, Florida

2 Sailings

Nov 30, 2025 - Feb 22, 2026

2 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$1,704

per person*

taxes & fees included

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

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

11-night Southern Caribbean Islander Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

Published prices from

$1,834

per person*

taxes & fees included

5-night Caribbean Getaway With Grand Turk Cruise

Amber Cove

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 29, 2026

1 Sailing

Mar 29, 2026

Published prices from

$1,209

per person*

taxes & fees included

7-night Eastern Caribbean With Bahamas Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

7 Sailings

Dec 6, 2025 - Mar 14, 2026

7 Sailings

Dec 6, 2025 - Mar 14, 2026

Published prices from

$904

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.

14-night Circle the Caribbean Cruise