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.
5,314 cruises cruises
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
|
22-night Star Collector – Fall Leaves and Caribbean Breezes Cruise
Montreal to San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/12/24
|
From
$9,839
|
|
11-night Boston Sights, Warm Caribbean Nights Cruise
Boston to San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/23/24
|
From
$2,799
|
|
6-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$2,499
|
|
13-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/3/24
|
From
$4,399
|
|
14-night Ocean Crossing Cruise
Lisbon to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
11/5/24
|
From
$2,399
|
|
7-night Windward Islands Surf and Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/24
|
From
$2,899
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/9/24
|
From
$4,399
|
|
14-night Ocean Crossing Cruise
Lisbon to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
11/13/24
|
From
$2,499
|
|
7-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/16/24
|
From
$2,499
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/16/24
|
From
$3,999
|
|
11-night Colombian and Southern Caribbean Coastlines Cruise
Bridgetown (Barbados) to Colon (Panama) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
11/19/24
|
From
$3,499
|
|
18-night Star Collector – Reefs and Rainforests – the Caribbean, Colombia, Panama, and Costa Rica via the Panama Canal Cruise
Bridgetown (Barbados) to Puerto Caldera |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
11/19/24
|
From
$5,499
|
|
14-night Star Collector – Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/23/24
|
From
$4,199
|
|
7-night Windward Islands Surf and Sunsets Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/23/24
|
From
$2,499
|
|
10-night Hidden Treasures of the Lesser Antilles Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
11/27/24
|
From
$3,699
|
|
7-night San Juan and the Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/30/24
|
From
$2,599
|
|
7-night Winter Antilles Escape Cruise
San Juan to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/24
|
From
$2,499
|
|
7-night Jewels of the Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/7/24
|
From
$2,499
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/7/24
|
From
$3,999
|
|
14-night Star Collector – White Sands of the Windward Islands Cruise
San Juan to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/7/24
|
From
$3,999
|
|
7-night Windward Ways and Tobago Cays Cruise
Bridgetown (Barbados) to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
12/14/24
|
From
$2,499
|
|
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
12/14/24
|
From
$4,399
|
|
7-night Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/14/24
|
From
$2,499
|
|
14-night Star Collector – Windward Treasures – An Antilles Odyssey Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
12/14/24
|
From
$4,299
|