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Caribbean Cruises Starting In September 2026, 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in September 2026, 2027, 2028 or 2029? Choose from 100 unique cruises and 1,568 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveler reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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100 Cruises (1,568 Cruise Departures)
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: May 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$839
Oceanview
$949
Balcony
$1,175
Suite
$1,190
From
US$839
Save 887
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Inside
$419
Oceanview
$539
Balcony
$621
Suite
$1,461
From
US$419
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Apr 2027 to Apr 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: May 2026 to Mar 2028
Visit: Colombia, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$866
Oceanview
$997
Balcony
$1,341
Suite
$1,401
From
US$866
Save 1,118
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: May 2026 to Oct 2026
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$895
Oceanview
$1,045
Balcony
$1,195
Suite
$2,145
From
US$895
Per Person
View Trip
8 Day Western Caribbean with Mexico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Star Princess
Departures: Jul 2026 to Mar 2027
Visit: USA, Honduras, Belize, Mexico
Princess Standard
Sanctuary Collection
Inside
$479
Oceanview
$689
Balcony
$554
Suite
$829
From
US$479
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic (+3 more), Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$729
Oceanview
$809
Balcony
$979
Suite
$1,079
From
US$729
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Apr 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$645
Oceanview
$745
Balcony
$895
Suite
$2,500
From
US$645
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Sep 2026 to Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Honduras, Belize, Mexico
Princess Standard
Inside
$938
Oceanview
-
Balcony
$1,078
Suite
$1,768
From
US$938
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
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$529
Oceanview
$579
Balcony
$799
Suite
$899
From
US$529
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Dominican Republic
Inside
$836
Oceanview
$1,076
Balcony
$1,456
Suite
$2,960
From
US$836
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Inside
$846
Oceanview
$1,086
Balcony
$1,496
Suite
$2,980
From
US$846
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
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic, Norwegian Prima
Departures: May 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$849
Balcony
$979
Suite
$1,219
From
US$699
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico
Inside
$419
Oceanview
$539
Balcony
$620
Suite
$1,511
From
US$419
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,448
From
US$689
Save 568
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Sep 2026 to Apr 2028
Visit: Panama, Colombia, Bonaire, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$973
Oceanview
$1,104
Balcony
$1,543
Suite
$1,643
From
US$973
Save 621
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Sep 2026 to Sep 2026
Visit: USA, Honduras, Belize, Mexico, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Inside
$938
Oceanview
-
Balcony
$1,188
Suite
$1,688
From
US$938
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$806
Oceanview
$728
Balcony
$1,213
Suite
$1,402
From
US$728
Save 630
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Sep 2026 to Apr 2028
Visit: Colombia, Bonaire, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$1,020
Oceanview
$1,160
Balcony
$1,640
Suite
$1,750
From
US$1,020
Save 762
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Sep 2026 to Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Inside
$499
Oceanview
-
Balcony
$624
Suite
$949
From
US$499
Per Person
View Trip
8 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: Jun 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,315
Oceanview
$1,520
Balcony
$1,642
Suite
$2,975
From
US$1,315
Save 1,025
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2027 to Sep 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,047
Oceanview
$1,121
Balcony
$1,171
Suite
$2,427
From
US$1,047
Save 658
Per Person
View Trip
7 Day Cayman, Mexico & Bahamas Holiday with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Sep 2026 to Dec 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$707
Oceanview
$863
Balcony
$866
Suite
$2,317
From
US$707
Save 754
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Inside
$1,171
Oceanview
$1,581
Balcony
$1,901
Suite
$3,591
From
US$1,171
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$708
Oceanview
$972
Balcony
$1,291
Suite
$2,470
From
US$708
Save 507
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ships: Celebrity Beyond, Celebrity Xcel
Departures: Nov 2026 to Oct 2027
Visit: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,097
Oceanview
$1,184
Balcony
$1,419
Suite
$3,739
From
US$1,097
Save 988
Per Person
View Trip
9 Day Aruba, Curacao & Bonaire Cruise with Celebrity Cruises
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Beyond, Celebrity Reflection, Celebrity Silhouette
Departures: Sep 2026 to Apr 2028
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$848
Oceanview
$970
Balcony
$1,106
Suite
$2,953
From
US$848
Save 1,137
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Jun 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Inside
$1,161
Oceanview
$1,591
Balcony
$1,891
Suite
$3,591
From
US$1,161
Per Person
View Trip
9 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departures: May 2026 to Oct 2027
Visit: USA, Curacao, Aruba, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$988
Oceanview
$1,242
Balcony
$1,250
Suite
$2,929
From
US$988
Save 871
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Dec 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$659
Oceanview
$749
Balcony
$1,192
Suite
$1,471
From
US$659
Save 533
Per Person
View Trip
Results: 1-30 of 100

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