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.

79-night Circle South America Grand Voyage

Roundtrip Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
1/6/26
From
$26,759
11-night Eastern Caribbean Voyage

Miami to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
1/6/26
From
$3,039
22-night Barbados To Brazil & Buenos Aires Voyage

Bridgetown (Barbados) to Buenos Aires

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
1/17/26
From
$8,109
11-night Caribbean Quest Voyage

Fuerte Amador (Panama City) to Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
3/15/26
From
$3,799
12-night Transatlantic Voyage: Florida, Bermuda & Portugal

Miami to Lisbon

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
3/26/26
From
$2,229
56-night Grand Voyage: Venice to Miami

Venice to Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Onward
Departs
10/6/26
 
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26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados

Montreal to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
10/19/26
From
$6,279
9-night Bermuda & Caribbean Voyage: New York, Bermuda & St. Maarten

New York City to San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
10/29/26
From
$1,449
16-night Caribbean Voyage: New York, Bermuda & Barbados

New York City to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
10/29/26
From
$2,669
38-night Athens To Miami Grand Voyage

Athens (Piraeus) to Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
10/31/26
From
$10,859
14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts

Roundtrip San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/7/26
From
$2,549
7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados

San Juan to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/7/26
From
$1,299
7-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts

Bridgetown (Barbados) to San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/14/26
From
$1,399
14-night Caribbean Voyage: Barbados, St. Lucia & St. Kitts

Roundtrip Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/14/26
From
$2,549
7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados

San Juan to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/21/26
From
$1,299
14-night Caribbean Voyage: San Juan, Antigua & Barbados

Roundtrip San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/21/26
From
$2,539
15-night Transatlantic Voyage: Lisbon, Tenerife & Miami

Lisbon to Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
11/23/26
From
$2,419
14-night Caribbean Voyage: Barbados, St. Lucia & St. Maarten

Roundtrip Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/28/26
From
$2,539
7-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts

Bridgetown (Barbados) to San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
11/28/26
From
$1,399
7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados

San Juan to Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
12/5/26
From
$1,299
13-night Caribbean Voyage: San Juan, Antigua & St. Lucia

Roundtrip San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
12/5/26
From
$2,359
10-night Eastern Caribbean Voyage: St.Maarten, St.Kitts & Miami

Roundtrip Miami

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Quest
Departs
12/8/26
From
$1,799
16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas

Roundtrip Bridgetown (Barbados)

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
12/12/26
From
$2,859
6-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts

Bridgetown (Barbados) to San Juan

Cruise Line
Azamara Cruises
Cruise Ship
Azamara Journey
Departs
12/12/26
From
$1,139