Caribbean Cruises Starting In October 2026, 2027, 2028 and 2029
Are you planning a cruise to the Caribbean in October 2026, 2027, 2028 or 2029? Choose from 210 unique cruises and 1,989 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveller reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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210 Cruises(1,989 Departures)
210 Cruises(1,989 Departures)
Departures
Oct 2027
(102)
Oct 2028
(33)
Oct 2029
(1)
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Mega Cruise Ships
(102)
Large Cruise Ships
(74)
Mid-Size Cruise Ships
(8)
Small Cruise Ships
(22)
Expedition Cruise Ships
(4)
Anguilla
(2)
Antarctica
(1)
Antigua and Barbuda
(40)
Argentina
(2)
Aruba
(41)
Bahamas
(109)
Barbados
(27)
Belize
(15)
Bermuda
(12)
Bonaire
(19)
Brazil
(5)
Canada
(8)
Cayman Islands
(23)
Chile
(2)
Colombia
(18)
Costa Rica
(13)
Curacao
(40)
Dominica
(10)
Dominican Republic
(71)
Ecuador
(1)
England
(5)
Falkland Islands
(1)
France
(4)
French Guiana
(5)
Grenada
(6)
Guadeloupe
(13)
Guatemala
(5)
Haiti
(3)
Holland
(1)
Honduras
(26)
Italy
(5)
Jamaica
(19)
Malta
(1)
Martinique
(19)
Mexico
(67)
Montserrat
(1)
Morocco
(4)
Nicaragua
(1)
Panama
(19)
Peru
(2)
Portugal
(5)
Puerto Rico
(47)
Saint Barthelemy
(12)
Saint Kitts and Nevis
(31)
Saint Lucia
(25)
Saint Martin
(35)
Saint Vincent
(8)
Sardinia
(1)
Sicily
(1)
Sint Maarten
(7)
Spain
(17)
Trinidad and Tobago
(8)
Tunisia
(1)
Turks and Caicos Islands
(34)
Uruguay
(2)
USA
(180)
Virgin Islands
(53)
Visits:
USA, Turks and Caicos Islands, Curacao, Bonaire +7 more, Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Visits:
USA, Puerto Rico, Antigua and Barbuda, Saint Lucia +7 more, Barbados, Saint Martin, Virgin Islands, Turks and Caicos Islands, Curacao, Bonaire, Aruba