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Caribbean Cruises Starting In October 2026 and 2027

Are you planning a cruise to the Caribbean in October 2026 or 2027? Choose from 184 unique cruises and 1,898 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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184 Cruises (1,898 Cruise Departures)
8 Day Tortola, St. Kitts & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$895
Oceanview
$958
Balcony
$1,079
Suite
$3,258
From
US$895
Save 794
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
$1,499
Oceanview
$1,609
Balcony
-
Suite
$2,099
From
US$1,499
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
$878
Oceanview
-
Balcony
$1,013
Suite
$1,658
From
US$878
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
7 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Aug 2026 to Mar 2027
Visit: USA, Mexico, Cayman Islands, Bahamas
Exclusive Savings
Inside
$703
Oceanview
$753
Balcony
$849
Suite
$1,994
From
US$703
Save 569
Per Person
View Trip
22 Day Southern Caribbean: Cabo Rojo & ABC Islands with Holland America
Cruise

22 Days (21 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 31 October 2026
Visit: USA, Saint Martin, Antigua and Barbuda, Martinique (+8 more), Dominica, Saint Kitts and Nevis, Virgin Islands, Bahamas, Bonaire, Curacao, Aruba, Dominican Republic
Fare Saver
Inside
$1,679
Oceanview
$2,089
Balcony
$2,449
Suite
$5,329
From
US$1,679
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$534
Oceanview
$584
Balcony
$634
Suite
$1,189
From
US$534
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
$794
Oceanview
$894
Balcony
$1,019
Suite
$2,700
From
US$794
Save 1,165
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
7 Day Key West, Mexico & Cayman with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Apr 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$762
Oceanview
$862
Balcony
$892
Suite
$1,904
From
US$762
Save 770
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: MSC Cruises
Ship: MSC Seascape
Departures: Apr 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Inside
$339
Oceanview
$409
Balcony
$519
Suite
$1,195
From
US$339
Per Person
View Trip
8 Day Eastern Caribbean with Celebration Key with Princess
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Star Princess
Departure: 31 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$679
Oceanview
$799
Balcony
$1,209
Suite
$1,599
From
US$679
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: 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 Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Jewel of the Seas, Serenade of the Seas
Departures: Oct 2026 to Nov 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$522
Oceanview
$582
Balcony
$675
Suite
$1,294
From
US$522
Save 384
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: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$693
Oceanview
$790
Balcony
$890
Suite
$2,402
From
US$693
Save 790
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$929
Oceanview
$979
Balcony
$1,154
Suite
$3,554
From
US$929
Save 601
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
Limited Time Offer
Inside
-
Oceanview
$1,314
Balcony
$1,374
Suite
$2,874
From
US$1,314
Per Person
View Trip
6 Day Western Caribbean Getaway Cruise with Royal Caribbean
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ships: Liberty of the Seas, Symphony of the Seas
Departures: Nov 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$511
Oceanview
$583
Balcony
$663
Suite
$1,281
From
US$511
Save 526
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
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
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 29 October 2027
Visit: Puerto Rico, Aruba, Curacao, Barbados, Dominica, Antigua and Barbuda, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$867
Oceanview
$956
Balcony
$1,627
Suite
$1,777
From
US$867
Save 465
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
Limited Time Offer
Inside
$1,043
Oceanview
$1,253
Balcony
$1,533
Suite
$4,053
From
US$1,043
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
$909
Balcony
$1,009
Suite
$1,209
From
US$759
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

16 Days (15 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visit: USA, Cayman Islands, Jamaica, Bonaire, Aruba, Curacao, Dominican Republic
Inside
$1,316
Oceanview
$1,506
Balcony
$1,921
Suite
$9,401
From
US$1,316
Per Person
View Trip
8 Day Tortola, St. Maarten & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$848
Oceanview
$948
Balcony
$1,139
Suite
$3,562
From
US$848
Save 806
Per Person
View Trip
22 Day Southern Caribbean & Panama Canal: ABC Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba (+5 more), Bahamas, Colombia, Panama, Costa Rica, Jamaica
Fare Saver
Inside
$1,839
Oceanview
$2,199
Balcony
$2,919
Suite
$5,979
From
US$1,839
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ships: Icon Of The Seas, Liberty of the Seas, Symphony of the Seas
Departures: May 2026 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$643
Oceanview
$780
Balcony
$984
Suite
$1,961
From
US$643
Save 916
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: May 2027 to Oct 2027
Visit: USA, Curacao, Bonaire, Aruba, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,205
Oceanview
$1,298
Balcony
$2,224
Suite
$2,461
From
US$1,205
Save 639
Per Person
View Trip
11 Day Western Caribbean: Greater Antilles, Belize & Mexico with Holland America
Cruise
 (3)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Honduras, Belize, Mexico
Fare Saver
Inside
$899
Oceanview
$1,149
Balcony
$1,299
Suite
$1,999
From
US$899
Per Person
View Trip
Results: 1-30 of 184

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