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 80 unique cruises and 1,643 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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80 Cruises (1,643 Departures)
80 Cruises (1,643 Departures)
Departures
Duration
5 Days
81 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$300pp
$191,550pp
Countries
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Cruise
 (1)

6 Days (5 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Departures: Apr 2028 to Sep 2028
Visits: USA, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$785
Oceanview
$924
Balcony
$1,117
Suite
$1,542
From (Per Person)
A$785
Per Person
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Departures: Nov 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,053
Oceanview
$1,142
Balcony
$1,246
Suite
$1,857
From (Per Person)
A$1,053
Save 23
Per Person
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,379
Oceanview
$1,726
Balcony
$2,191
Suite
$4,240
From (Per Person)
A$1,379
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Nov 2026 to Nov 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$626
Oceanview
$764
Balcony
$962
Suite
$1,863
From (Per Person)
A$626
Save 14
Per Person
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Departures: May 2027 to Sep 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,018
Oceanview
$1,102
Balcony
$1,589
Suite
$2,176
From (Per Person)
A$1,018
Save 895
Per Person
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Departures: Dec 2026 to Mar 2028
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$575
Oceanview
$695
Balcony
$754
Suite
$933
From (Per Person)
A$575
Save 13
Per Person
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Departures: Aug 2027 to Sep 2027
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,274
Oceanview
$1,312
Balcony
$1,278
Suite
$3,474
From (Per Person)
A$1,274
Save 971
Per Person
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Departures: May 2027 to Oct 2027
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,639
Oceanview
$1,746
Balcony
$2,073
Suite
$5,314
From (Per Person)
A$1,639
Save 1,488
Per Person
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,330
Oceanview
$1,607
Balcony
$2,043
Suite
$4,072
From (Per Person)
A$1,330
Per Person
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Departures: Jun 2027 to Sep 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,001
Oceanview
$1,044
Balcony
$1,596
Suite
$2,351
From (Per Person)
A$1,001
Save 693
Per Person
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Departures: May 2027 to Jun 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,027
Oceanview
$1,075
Balcony
$1,645
Suite
$2,500
From (Per Person)
A$1,027
Save 836
Per Person
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Departures: Jun 2027 to Oct 2028
Visits: USA, Dominican Republic, Bahamas
Inside
$863
Oceanview
$1,081
Balcony
$1,298
Suite
$3,845
From (Per Person)
A$863
Per Person
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Departures: Jul 2027 to Sep 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,377
Oceanview
$1,377
Balcony
$1,509
Suite
$4,568
From (Per Person)
A$1,377
Save 1,194
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$886
Oceanview
$976
Balcony
$1,140
Suite
$1,408
From (Per Person)
A$886
Save 18
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Departures: Dec 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,528
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
Per Person
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$636
Oceanview
$774
Balcony
$1,022
Suite
$2,002
From (Per Person)
A$636
Save 16
Per Person
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Departures: Nov 2026 to Oct 2027
Visits: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,641
Oceanview
$1,824
Balcony
$1,873
Suite
$5,280
From (Per Person)
A$1,641
Save 1,511
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$626
Oceanview
$764
Balcony
$982
Suite
$2,031
From (Per Person)
A$626
Save 51
Per Person
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Departures: Dec 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$935
Oceanview
$1,082
Balcony
$1,227
Suite
$2,677
From (Per Person)
A$935
Per Person
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Exclusive Savings
Inside
$964
Oceanview
$1,162
Balcony
$1,697
Suite
$2,498
From (Per Person)
A$964
Save 15
Per Person
Cruise

7 Days (6 Nights) Miami to Miami
Operator: Royal Caribbean
Departures: Jun 2028 to Sep 2028
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,257
Oceanview
$1,369
Balcony
$1,529
Suite
$2,717
From (Per Person)
A$1,257
Save 899
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,141
Oceanview
$1,587
Balcony
$1,587
Suite
$1,989
From (Per Person)
A$1,141
Save 22
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Nov 2027 to Nov 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,408
Oceanview
$1,685
Balcony
$1,824
Suite
$2,398
From (Per Person)
A$1,408
Per Person
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Departures: May 2027 to Oct 2027
Visits: USA, Bahamas, Jamaica
Exclusive Savings
Inside
$1,146
Oceanview
$1,325
Balcony
$1,317
Suite
$2,507
From (Per Person)
A$1,146
Save 958
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Departures: Nov 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$824
Oceanview
$942
Balcony
$1,230
Suite
$2,398
From (Per Person)
A$824
Save 15
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: Jul 2028 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,918
Oceanview
$2,239
Balcony
$2,372
Suite
$4,887
From (Per Person)
A$1,918
Save 1,403
Per Person
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Departures: Aug 2027 to Jan 2029
Visits: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$922
Oceanview
$989
Balcony
$1,103
Suite
$3,531
From (Per Person)
A$922
Save 950
Per Person
Cruise

9 Days (8 Nights) Miami to Miami
Operator: Royal Caribbean
Departures: Jul 2028 to Sep 2028
Visits: USA, Bahamas, Dominican Republic, Aruba, Curacao
Exclusive Savings
Inside
$1,652
Oceanview
$1,805
Balcony
$2,035
Suite
$3,668
From (Per Person)
A$1,652
Save 1,244
Per Person
Cruise

10 Days (9 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: Sep 2027
Visits: USA, Bahamas, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,805
Oceanview
$2,237
Balcony
$3,070
Suite
$3,951
From (Per Person)
A$1,805
Save 1,027
Per Person
Cruise

8 Days (7 Nights) La Romana to La Romana
Operator: MSC Cruises
Ship: MSC Opera
Departures: Nov 2026 to Nov 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Exclusive Savings
Inside
$984
Oceanview
$1,271
Balcony
$1,855
Suite
$2,726
From (Per Person)
A$984
Per Person
Results: 1-30 of 80

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