Caribbean Cruises Starting In October 2026 and 2027

Filter Results
Departures
Duration
5 Days
58 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$100pp
$130,398pp
Countries
Show More...
Filter Results
173 Cruises (1,943 Cruise Departures)
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Inside
$969
Oceanview
$1,099
Balcony
$1,339
Suite
$3,499
From
US$969
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$925
Oceanview
$1,125
Balcony
$1,450
Suite
$1,650
From
US$925
Per Person
View Trip
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$654
Oceanview
-
Balcony
$819
Suite
$1,139
From
US$654
Per Person
View Trip
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Nov 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$774
Oceanview
$894
Balcony
$1,039
Suite
$1,539
From
US$774
Per Person
View Trip
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$978
Oceanview
$1,068
Balcony
$1,418
Suite
$1,608
From
US$978
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 09 October 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$957
Oceanview
$1,107
Balcony
$1,137
Suite
$2,152
From
US$957
Save 506
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: May 2026 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$604
Oceanview
$723
Balcony
$904
Suite
$1,679
From
US$604
Save 867
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,398
From
US$689
Save 568
Per Person
View Trip
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 15 October 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Saint Martin, Virgin Islands, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Inside
$2,109
Oceanview
$2,289
Balcony
$2,669
Suite
$7,304
From
US$2,109
Per Person
View Trip
Cruise
 (2)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Apr 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$683
Oceanview
$872
Balcony
$880
Suite
$2,077
From
US$683
Save 901
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Jan 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$374
Oceanview
$409
Balcony
$562
Suite
$859
From
US$374
Save 792
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 22 October 2026
Visit: USA, Bahamas, Dominican Republic, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$1,457
Oceanview
$1,575
Balcony
$2,867
Suite
$3,220
From
US$1,457
Save 706
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 17 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Mexico, Belize, Honduras
Princess Standard
Inside
$918
Oceanview
-
Balcony
$1,238
Suite
$1,608
From
US$918
Per Person
View Trip
Cruise

11 Days (10 Nights) New York to Miami
Cruise Line: Royal Caribbean
Departure: 29 October 2026
Visit: USA, Dominican Republic, Aruba, Bonaire
Bonus Onboard Credit
Exclusive Savings
Inside
$1,005
Oceanview
$1,326
Balcony
$1,675
Suite
$2,785
From
US$1,005
Save 508
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,489
Oceanview
$1,839
Balcony
$2,118
Suite
$3,370
From
US$1,489
Save 64
Per Person
View Trip
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2027 to Oct 2027
Visit: USA, Curacao, Bonaire, Aruba, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,169
Oceanview
$1,323
Balcony
$2,224
Suite
$2,336
From
US$1,169
Save 658
Per Person
View Trip
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba, Bahamas
Fare Saver
Inside
$814
Oceanview
$1,014
Balcony
$1,314
Suite
$2,814
From
US$814
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,393
Oceanview
$1,524
Balcony
$1,693
Suite
$3,450
From
US$1,393
Save 907
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$719
Oceanview
$869
Balcony
$1,109
Suite
$1,249
From
US$719
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba (+5 more), Bahamas, Colombia, Panama, Costa Rica, Jamaica
Fare Saver
Inside
$1,959
Oceanview
$2,319
Balcony
$3,039
Suite
$6,270
From
US$1,959
Per Person
View Trip
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2026
Visit: USA, Bahamas, Aruba, Curacao
Exclusive Savings
Inside
$825
Oceanview
$1,095
Balcony
$1,175
Suite
$2,523
From
US$825
Save 755
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 08 October 2026
Visit: USA, Aruba, Curacao, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,263
Oceanview
$1,361
Balcony
$1,970
Suite
$2,922
From
US$1,263
Save 627
Per Person
View Trip
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
$1,759
Oceanview
$2,119
Balcony
$3,109
Suite
$6,155
From
US$1,759
Per Person
View Trip
Cruise
 (3)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Inside
$1,219
Oceanview
$1,419
Balcony
$2,019
Suite
$4,154
From
US$1,219
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$540
Oceanview
$599
Balcony
$1,429
Suite
$1,399
From
US$540
Save 353
Per Person
View Trip
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
Bonus Onboard Credit
Inside
$424
Oceanview
$474
Balcony
$614
Suite
$1,674
From
US$424
Per Person
View Trip
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$906
Oceanview
$1,084
Balcony
$973
Suite
$2,246
From
US$906
Save 559
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Departures: Oct 2027 to Apr 2028
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$836
Oceanview
$936
Balcony
$1,061
Suite
$2,561
From
US$836
Save 773
Per Person
View Trip
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda
Bonus Onboard Credit
Inside
$629
Oceanview
$789
Balcony
$1,199
Suite
$1,839
From
US$629
Per Person
View Trip
Cruise

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Apr 2027 to Feb 2028
Visit: USA, Bahamas, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$579
Oceanview
$656
Balcony
$661
Suite
$1,058
From
US$579
Save 576
Per Person
View Trip
Results: 61-90 of 173

No results found. Try amending the search filters.

Routes

Cruises from Baltimore to Baltimore Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to Lisbon Cruises from Barcelona to Rome Cruises from Barcelona to Barcelona Cruises from Barcelona to Miami Cruises from Boston to Boston Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Buenos Aires to Rio de Janeiro Cruises from Buenos Aires to Buenos Aires Cruises from Cartagena to Cartagena Cruises from Colon to Colon Cruises from Fort Lauderdale to Los Angeles Cruises from Fort Lauderdale to Barcelona Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort Lauderdale to San Diego Cruises from Fort Lauderdale to Vancouver Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from Genoa to Genoa Cruises from Hamburg to London Cruises from Hamburg to Hamburg Cruises from Jacksonville to Jacksonville Cruises from La Romana to La Romana Cruises from Lisbon to Lisbon Cruises from Lisbon to London Cruises from Lisbon to Barcelona Cruises from Lisbon to Rome Cruises from London to Hamburg Cruises from London to Barcelona Cruises from London to Fort Lauderdale Cruises from London to Reykjavik Cruises from London to London Cruises from London to Lisbon Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Los Angeles to Vancouver Cruises from Los Angeles to Los Angeles Cruises from Marseille to Marseille Cruises from Miami to San Juan Cruises from Miami to Lisbon Cruises from Miami to Los Angeles Cruises from Miami to Rome Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Miami to Barcelona Cruises from Miami to Miami Cruises from Miami to London Cruises from Montreal to Boston Cruises from Montreal to Miami Cruises from Montreal to New York Cruises from New Orleans to New Orleans Cruises from New York to New York Cruises from New York to London Cruises from Orlando to Orlando Cruises from Philadelphia to Philadelphia Cruises from Pointe-A-Pitre to Pointe-A-Pitre Cruises from Quebec City to Boston Cruises from Reykjavik to London Cruises from Reykjavik to Reykjavik Cruises from Rio de Janeiro to Rio de Janeiro Cruises from Rio de Janeiro to Barcelona Cruises from Rome to Lisbon Cruises from Rome to Miami Cruises from Rome to Barcelona Cruises from Rome to Fort Lauderdale Cruises from Rome to Rome Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Santiago to Buenos Aires Cruises from Santiago to Santiago Cruises from Seattle to Vancouver Cruises from Seattle to Seattle Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Venice to Barcelona Cruises from Venice to Rome

Country Routes

Cruises from Peru to Argentina Cruises from USA to Portugal Cruises from Germany to England Cruises from France to Spain Cruises from Portugal to England Cruises from Iceland to USA Cruises from Puerto Rico to USA Cruises from Chile to USA Cruises from USA to Iceland Cruises from France to Brazil Cruises from Brazil to France Cruises from Iceland to Canada Cruises from England to Germany Cruises from Singapore to China Cruises from Dominican Republic to USA Cruises from Brazil to Spain Cruises from USA to Puerto Rico Cruises from Argentina to Brazil Cruises from USA to Brazil Cruises from Argentina to Chile Cruises from Brazil to Italy Cruises from Argentina to USA Cruises from Peru to USA Cruises from Barbados to USA Cruises from Canada to USA Cruises from Chile to Argentina Cruises from England to Iceland Cruises from England to Spain Cruises from England to USA Cruises from France to Italy Cruises from USA to Dominican Republic Cruises from Iceland to England Cruises from Italy to Brazil Cruises from Italy to France Cruises from Italy to Portugal Cruises from Italy to Spain Cruises from Italy to USA Cruises from Panama to USA Cruises from Spain to Brazil Cruises from Portugal to Italy Cruises from Portugal to Spain Cruises from Portugal to USA Cruises from Barbados to Saint Martin Cruises from Spain to France Cruises from Spain to Italy Cruises from Spain to Portugal Cruises from Spain to USA Cruises from USA to Barbados Cruises from USA to Canada Cruises from England to Portugal Cruises from USA to Chile Cruises from USA to England Cruises from USA to Italy Cruises from Spain to England Cruises from USA to Panama Cruises from USA to Peru Cruises from USA to Spain