The Caribbean has been a haven for seafarers for centuries and is now considered heaven for modern-day travelers. With hundreds of unique islands and thousands of miles of unspoiled beaches dotted with secret bays, hidden coves and incredible ports of call, the Caribbean is widely considered among the world’s best vacation destinations.
Whether you enjoy the hustle and bustle of busy island ports, the sanctitude and solitude of hidden beaches, or fishing, diving and other aquatic adventures, there is something for every age and activity level in the breathtaking Caribbean islands of the Bahamas, Barbados, Virgin Islands, Cuba, Jamaica, Martinique, Puerto Rico, Trinidad and Tobago, Turks and Caicos, West Indies and more.
There are dozens of Caribbean cruise options to choose from, so speak to a CruiseInsider today at 1 (877) 734-6858 to start planning your island adventure or choose from one of the many Caribbean voyages offered below.
5,301 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
7-night Panama Canal, Cartagena, San Blas Islands, and More Cruise
Oranjestad, Aruba to Fuerte Amador |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/21/24
|
From
$2,999
|
|
7-night Jewels of the Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/21/24
|
From
$2,899
|
|
7-night Classic Caribbean Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
12/21/24
|
From
$2,999
|
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
12/21/24
|
From
$5,199
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/21/24
|
From
$4,699
|
|
7-night Panama Canal, Cartagena, San Blas Islands, and More Cruise
Fuerte Amador to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/28/24
|
From
$3,499
|
|
14-night Star Collector – Windward Islands and Spanish New World Cruise
Fuerte Amador to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/28/24
|
From
$4,799
|
|
7-night Beach Fun & Sun – A Remote Caribbean Getaway Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
12/28/24
|
From
$3,499
|
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
12/28/24
|
From
$5,199
|
|
7-night Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/28/24
|
From
$2,899
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/28/24
|
From
$4,399
|
|
7-night Windward Ways and Tobago Cays Cruise
Oranjestad, Aruba to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/4/25
|
From
$2,599
|
|
7-night Jewels of the Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
1/4/25
|
From
$2,599
|
|
7-night Classic Caribbean Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
1/4/25
|
From
$2,599
|
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
1/4/25
|
From
$4,599
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
1/4/25
|
From
$4,199
|
|
7-night Windward Ways and Tobago Cays Cruise
Bridgetown (Barbados) to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/11/25
|
From
$2,799
|
|
14-night Star Collector – Windward Islands and Spanish New World Cruise
Bridgetown (Barbados) to Fuerte Amador |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/11/25
|
From
$4,299
|
|
7-night Beach Fun & Sun – A Remote Caribbean Getaway Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
1/11/25
|
From
$2,799
|
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
1/11/25
|
From
$4,799
|
|
7-night Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
1/11/25
|
From
$2,699
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
1/11/25
|
From
$4,399
|
|
7-night Panama Canal, Cartagena, San Blas Islands, and More Cruise
Oranjestad, Aruba to Fuerte Amador |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
1/18/25
|
From
$2,599
|
|
7-night Jewels of the Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
1/18/25
|
From
$2,799
|