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.
6,130 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
Fuerte Amador to Oranjestad, Aruba |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
3/8/25
|
From
$3,265
|
18-night Star Collector – Reefs and Rainforests – the Caribbean, Colombia, Panama, and Costa Rica via the Panama Canal Cruise
Puerto Caldera to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
3/8/25
|
Call For Pricing
|
7-night Beach Fun & Sun – A Remote Caribbean Getaway Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/8/25
|
Call For Pricing
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/8/25
|
From
$11,019
|
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
3/8/25
|
Call For Pricing
|
11-night Colombian and Southern Caribbean Coastlines Cruise
Colon (Panama) to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
3/15/25
|
From
$4,780
|
7-night Classic Caribbean Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/15/25
|
From
$3,551
|
14-night Star Collector – Caribbean Explorations Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/15/25
|
From
$5,719
|
7-night Windward Ways and Tobago Cays Cruise
Oranjestad, Aruba to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
3/15/25
|
From
$3,220
|
7-night Beach Fun & Sun – A Remote Caribbean Getaway Cruise
Roundtrip St. Maarten (Philipsburg) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/22/25
|
From
$3,567
|
7-night Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
3/22/25
|
Call For Pricing
|
15-night Ocean Crossing Cruise
Bridgetown (Barbados) to Lisbon |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
3/26/25
|
From
$3,125
|
25-night Star Collector – Classic Crossing to Spain and More Cruise
Bridgetown (Barbados) to Barcelona |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Star
|
Departs
3/26/25
|
Call For Pricing
|
7-night Jewels of the Windward Islands Cruise
Roundtrip Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
3/29/25
|
From
$3,038
|
14-night Ocean Crossing and Ponta Delgada, Azores Cruise
St. Maarten (Philipsburg) to Lisbon |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/29/25
|
From
$2,826
|
22-night Star Collector – Atlantic Interludes and Iberian Indulgences Cruise
St. Maarten (Philipsburg) to Barcelona |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Surf
|
Departs
3/29/25
|
From
$7,788
|
10-night Ocean Crossing Cruise
Bridgetown (Barbados) to Santa Cruz de Tenerife |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
4/5/25
|
From
$2,704
|
18 night Star Collector – Song of the Canaries – A Transatlantic Crossing
Bridgetown (Barbados) to Lisbon |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
4/5/25
|
From
$5,267
|
7-night Bermuda Bliss Cruise
New York City to San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/19/25
|
From
$2,426
|
24-night Star Collector: Classic Crossing To Spain & More Cruise
Barcelona to Bridgetown (Barbados) |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
10/25/25
|
From
$6,390
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
10/26/25
|
From
$5,162
|
7-night San Juan & The Virgin Islands Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/2/25
|
From
$2,862
|
14-night Star Collector: Lovely Leewards Cruise
Roundtrip San Juan |
Cruise Line
Windstar Cruises
|
Cruise Ship
Star Pride
|
Departs
11/2/25
|
From
$4,693
|
14-night Ocean Crossings
Lisbon to Barbados |
Cruise Line
Windstar Cruises
|
Cruise Ship
Wind Spirit
|
Departs
11/4/25
|
From
$2,625
|