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Caribbean Cruises Starting In September 2026, 2027 and 2028

Are you planning a cruise to the Caribbean in September 2026, 2027 or 2028? Choose from 94 unique cruises and 1,618 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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94 Cruises (1,618 Cruise Departures)
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$469
Oceanview
$459
Balcony
$669
Suite
$829
From
US$459
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
Limited Time Offer
Inside
$1,102
Oceanview
$1,095
Balcony
$1,245
Suite
$2,395
From
US$1,095
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
$569
Oceanview
$629
Balcony
$779
Suite
$929
From
US$569
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
$449
Oceanview
$569
Balcony
$739
Suite
$1,511
From
US$449
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
Limited Time Offer
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$469
Oceanview
$589
Balcony
$679
Suite
$1,319
From
US$469
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
$798
Oceanview
-
Balcony
$973
Suite
$1,548
From
US$798
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
$1,051
Oceanview
$1,244
Balcony
$1,284
Suite
$2,929
From
US$1,051
Save 823
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Apr 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas
Inside
$569
Oceanview
$858
Balcony
$968
Suite
$1,458
From
US$569
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: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$719
Oceanview
$809
Balcony
$949
Suite
$1,079
From
US$719
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: Apr 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Inside
$435
Oceanview
$525
Balcony
$655
Suite
$1,461
From
US$435
Per Person
View Trip
7 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2026 to Sep 2026
Visit: USA, Jamaica, Cayman Islands, Bahamas
Exclusive Savings
Inside
$660
Oceanview
$871
Balcony
$1,073
Suite
$1,513
From
US$660
Save 519
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,440
Oceanview
$1,560
Balcony
$1,680
Suite
$3,160
From
US$1,440
Save 1,028
Per Person
View Trip
9 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departures: Aug 2026 to Sep 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,131
Oceanview
$1,247
Balcony
$1,100
Suite
$2,650
From
US$1,100
Save 694
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: Harmony of the Seas
Departures: Aug 2027 to Sep 2027
Visit: USA, Bahamas, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$895
Oceanview
$1,035
Balcony
$1,065
Suite
$2,060
From
US$895
Save 609
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
Senior Discount
Exclusive Savings
Inside
$825
Oceanview
$732
Balcony
$1,178
Suite
$1,423
From
US$732
Save 521
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
$906
Oceanview
$1,146
Balcony
$1,556
Suite
$2,980
From
US$906
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
$409
Oceanview
$599
Balcony
$459
Suite
$729
From
US$409
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$824
Oceanview
$855
Balcony
$1,059
Suite
$2,732
From
US$824
Save 1,181
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise
 (1)

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Grandeur of the Seas (+3 more), Jewel of the Seas, Radiance of the Seas, Serenade of the Seas
Departures: Apr 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$359
Oceanview
$394
Balcony
$504
Suite
$859
From
US$359
Save 1,161
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
10 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2027 to Sep 2027
Visit: USA, Bahamas, Aruba, Bonaire, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$1,056
Oceanview
$1,259
Balcony
$1,991
Suite
$2,129
From
US$1,056
Save 553
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
$1,051
Oceanview
$1,170
Balcony
$1,370
Suite
$3,896
From
US$1,051
Save 1,057
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$722
Oceanview
$932
Balcony
$1,062
Suite
$2,076
From
US$722
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
$1,259
From
US$699
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: May 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$748
Oceanview
$762
Balcony
$1,105
Suite
$1,067
From
US$748
Save 909
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
$1,222
Suite
$1,264
From
US$866
Save 1,072
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 20 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$938
Oceanview
-
Balcony
-
Suite
-
From
US$938
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Nov 2027
Visit: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
Results: 1-30 of 94

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