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Caribbean Cruises Starting In September 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in September 2027, 2028 or 2029? Choose from 68 unique cruises and 1,494 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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68 Cruises (1,494 Departures)
68 Cruises (1,494 Departures)
Departures
Duration
5 Days
81 Days
Start & End Cities
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Price
$300pp
$209,450pp
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8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$636
Oceanview
$814
Balcony
$1,081
Suite
$2,457
From (Per Person)
A$636
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,330
Oceanview
$1,686
Balcony
$2,221
Suite
$4,993
From (Per Person)
A$1,330
Save 21
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jul 2027 to Sep 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,526
Oceanview
$1,525
Balcony
$1,790
Suite
$4,758
From (Per Person)
A$1,525
Save 1,152
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic +3 more, Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$901
Oceanview
$1,170
Balcony
$1,274
Suite
$1,690
From (Per Person)
A$901
Save 18
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,270
Oceanview
$1,627
Balcony
$2,161
Suite
$4,924
From (Per Person)
A$1,270
Save 21
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Oct 2027
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,781
Oceanview
$1,999
Balcony
$2,321
Suite
$5,982
From (Per Person)
A$1,781
Save 1,526
Per Person
View Trip
6 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$664
Oceanview
$725
Balcony
$739
Suite
$843
From (Per Person)
A$664
Save 13
Per Person
View Trip
8 Day Caribbean Cruise From Galveston to Galveston with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Operator: Norwegian Cruise Line
Ships: Norwegian Escape, Norwegian Prima, Norwegian Viva
Departures: Oct 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,097
Oceanview
$1,202
Balcony
$1,350
Suite
$1,960
From (Per Person)
A$1,097
Save 23
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2027 to Sep 2027
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,434
Oceanview
$1,452
Balcony
$1,559
Suite
$4,142
From (Per Person)
A$1,434
Save 816
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Sep 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,047
Oceanview
$1,109
Balcony
$1,689
Suite
$2,312
From (Per Person)
A$1,047
Save 802
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2027 to Oct 2028
Visits: USA, Dominican Republic, Bahamas
Inside
$878
Oceanview
$1,100
Balcony
$1,320
Suite
$3,911
From (Per Person)
A$878
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ships: Brilliant Lady, Resilient Lady +2 more, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$952
Oceanview
$1,099
Balcony
$1,246
Suite
$2,649
From (Per Person)
A$952
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$715
Oceanview
$873
Balcony
$1,170
Suite
$2,210
From (Per Person)
A$715
Save 16
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic, Norwegian Escape
Departures: Dec 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,602
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ships: MSC Grandiosa, MSC World Atlantic
Departures: Nov 2026 to Nov 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$596
Oceanview
$774
Balcony
$1,041
Suite
$2,437
From (Per Person)
A$596
Save 14
Per Person
View Trip
6 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

6 Days (5 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2027 to Apr 2028
Visits: USA, Haiti, Bahamas
Exclusive Savings
Inside
$843
Oceanview
$859
Balcony
$958
Suite
$1,529
From (Per Person)
A$843
Save 549
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC World Atlantic
Departures: Jan 2028 to Oct 2028
Visits: USA, Bahamas, Mexico, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$2,696
Oceanview
$3,250
Balcony
$3,726
Suite
$6,577
From (Per Person)
A$2,696
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) La Romana to La Romana
Operator: MSC Cruises
Ship: MSC Opera
Departures: Jun 2027 to Oct 2028
Visits: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda, Barbados, Guadeloupe
Exclusive Savings
Inside
$2,224
Oceanview
$2,680
Balcony
$3,828
Suite
$5,669
From (Per Person)
A$2,224
Save 54
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Dec 2027
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,017
Oceanview
$1,188
Balcony
$1,723
Suite
$2,569
From (Per Person)
A$1,017
Save 836
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC World Atlantic
Departures: Dec 2027 to Oct 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Mexico
Exclusive Savings
Inside
$2,617
Oceanview
$3,171
Balcony
$3,468
Suite
$6,498
From (Per Person)
A$2,617
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Nov 2028
Visits: Martinique, Antigua and Barbuda, Dominican Republic, Barbados
Exclusive Savings
Inside
$1,103
Oceanview
$1,330
Balcony
$1,904
Suite
$2,825
From (Per Person)
A$1,103
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$853
Oceanview
$982
Balcony
$1,279
Suite
$2,556
From (Per Person)
A$853
Save 17
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Jewel of the Seas +2 more, Radiance of the Seas, Serenade of the Seas
Departures: Nov 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$582
Oceanview
$650
Balcony
$731
Suite
$1,324
From (Per Person)
A$582
Save 653
Per Person
View Trip
10 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

10 Days (9 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2027
Visits: USA, Bahamas, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,805
Oceanview
$2,197
Balcony
$3,070
Suite
$3,951
From (Per Person)
A$1,805
Save 1,027
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Exclusive Savings
Inside
$2,389
Oceanview
$2,617
Balcony
$2,449
Suite
$4,587
From (Per Person)
A$2,389
Per Person
View Trip
8 Day Western Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Radiance of the Seas, Serenade of the Seas
Departures: Jun 2027 to Nov 2027
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,039
Oceanview
$1,237
Balcony
$1,710
Suite
$2,376
From (Per Person)
A$1,039
Save 721
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Galveston to Galveston
Operator: MSC Cruises
Ship: MSC Seascape
Departures: Nov 2026 to Nov 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$695
Oceanview
$933
Balcony
$1,071
Suite
$2,121
From (Per Person)
A$695
Save 13
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) La Romana to La Romana
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,224
Oceanview
$2,670
Balcony
$3,828
Suite
$5,669
From (Per Person)
A$2,224
Save 66
Per Person
View Trip
7 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 19 September 2027
Visits: USA, Mexico, Bahamas
Exclusive Savings
Inside
$1,259
Oceanview
$1,354
Balcony
$1,406
Suite
$2,971
From (Per Person)
A$1,259
Save 708
Per Person
View Trip
8 Day Eastern Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Aura, Norwegian Luna
Departures: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,022
Oceanview
$1,096
Balcony
$1,572
Suite
$2,183
From (Per Person)
A$1,022
Save 25
Per Person
View Trip
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