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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 187 unique cruises and 1,840 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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187 Cruises (1,840 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 Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
-
Oceanview
$1,323
Balcony
$1,533
Suite
$4,123
From
US$1,323
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departures: Oct 2027 to Apr 2028
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$886
Oceanview
$988
Balcony
$1,171
Suite
$2,907
From
US$886
Save 723
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
7 Day Eastern Caribbean & Bimini Halloween with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 25 October 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
-
Oceanview
$1,374
Balcony
$1,554
Suite
$2,994
From
US$1,374
Per Person
View Trip
22 Day Panama Canal & Southern Caribbean: ABC Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 18 October 2026
Visit: USA, Bahamas, Aruba, Colombia (+5 more), Panama, Costa Rica, Cayman Islands, Dominican Republic, Curacao
Fare Saver
Inside
$1,844
Oceanview
$2,114
Balcony
$2,744
Suite
$5,804
From
US$1,844
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
13 Day Eastern Caribbean Celebration with Cunard
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Oct 2026 to Nov 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Bonus Onboard Credit
Inside
$999
Oceanview
$1,299
Balcony
$1,599
Suite
$4,499
From
US$999
Per Person
View Trip
14 Day Southern Caribbean From New York To Miami with Norwegian Cruise Line
Cruise
 (1)

14 Days (13 Nights) New York to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Sun
Departure: 24 October 2026
Visit: USA, Bermuda, Puerto Rico, Virgin Islands (+4 more), Curacao, Aruba, Dominican Republic, Bahamas
Inside
$1,669
Oceanview
$1,719
Balcony
$3,019
Suite
$4,769
From
US$1,669
Per Person
View Trip
22 Day Western & Eastern Caribbean: Mexico & Leeward Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 31 October 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands (+9 more), Honduras, Belize, Mexico, Saint Martin, Antigua and Barbuda, Dominica, Saint Lucia, Saint Kitts and Nevis, Virgin Islands
Fare Saver
Inside
$1,734
Oceanview
$2,184
Balcony
$2,544
Suite
$4,164
From
US$1,734
Per Person
View Trip
15 Day Circle Caribbean with Princess
Cruise
 (4)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Coral Princess
Departure: 15 October 2026
Visit: USA, Saint Martin, Saint Kitts and Nevis, Martinique (+5 more), Dominica, Grenada, Trinidad and Tobago, Aruba, Curacao
Princess Standard
Inside
$1,859
Oceanview
$1,699
Balcony
-
Suite
-
From
US$1,699
Per Person
View Trip
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 10 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$549
Oceanview
-
Balcony
$804
Suite
$1,049
From
US$549
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
11 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Dec 2027
Visit: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Inside
$898
Oceanview
$1,018
Balcony
$1,289
Suite
$3,509
From
US$898
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
Departure: 17 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Mexico, Belize, Honduras
Princess Standard
Inside
$998
Oceanview
-
Balcony
$1,068
Suite
-
From
US$998
Per Person
View Trip
6 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

6 Days (5 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visit: USA, Cayman Islands, Jamaica
Drinks & WiFi Package
Inside
$378
Oceanview
$448
Balcony
$609
Suite
$2,249
From
US$378
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
11 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (4)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Coral Princess, Enchanted Princess
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Princess Standard
Inside
$1,006
Oceanview
$1,124
Balcony
$1,291
Suite
$1,691
From
US$1,006
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 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
13 Day Panama Canal Discovery: Costa Rica & Greater Antilles with Holland America
Cruise
 (3)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Inside
$1,199
Oceanview
$1,349
Balcony
$1,899
Suite
$3,999
From
US$1,199
Per Person
View Trip
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 17 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$539
Oceanview
-
Balcony
$634
Suite
$849
From
US$539
Per Person
View Trip
8 Day Key West, Cayman & Mexico with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ships: Celebrity Apex
Departures: Oct 2026 to Nov 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$894
Oceanview
$994
Balcony
$1,189
Suite
$3,169
From
US$894
Save 1,122
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
Departure: 03 October 2026
Visit: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,038
Oceanview
-
Balcony
$1,448
Suite
$1,878
From
US$1,038
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
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Escape, Norwegian Viva
Departures: Oct 2026 to Apr 2028
Visit: USA, Mexico, Honduras, Belize
Inside
$759
Oceanview
$929
Balcony
$1,009
Suite
$1,209
From
US$759
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 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 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
8 Day Western Caribbean with Mexico From Fort Lauderdale with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Star Princess, Sun Princess
Departures: May 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Sanctuary Collection
Inside
$499
Oceanview
$749
Balcony
$524
Suite
$899
From
US$499
Per Person
View Trip
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