Caribbean

Destinations / Caribbean

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.

Caribbean Cruises

6,130 cruises cruises

Includes free extras and bonus savings available only from CruiseInsider.

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
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