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

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191 Cruises (1,786 Cruise Departures)
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Inside
$796
Oceanview
$1,036
Balcony
$1,446
Suite
$2,980
From
US$796
Per Person
View Trip
Cruise
 (5)

18 Days (17 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$4,129
Oceanview
$4,829
Balcony
$6,019
Suite
$9,599
From
US$4,129
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
$1,038
Oceanview
-
Balcony
$1,438
Suite
$1,928
From
US$1,038
Per Person
View Trip
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: May 2027 to Oct 2027
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,098
Oceanview
$1,209
Balcony
$1,414
Suite
$3,949
From
US$1,098
Save 1,014
Per Person
View Trip
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
Bonus Onboard Credit
Value Fare
Inside
$799
Oceanview
$949
Balcony
$1,099
Suite
$2,999
From
US$799
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 30 October 2027
Visit: USA, Mexico, Bahamas
Inside
$795
Oceanview
$895
Balcony
$1,095
Suite
$2,950
From
US$795
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$821
Oceanview
$919
Balcony
$1,159
Suite
$3,086
From
US$821
Save 577
Per Person
View Trip
Cruise
 (1)

13 Days (12 Nights) New York to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 October 2026
Visit: USA, Bermuda, Bahamas, Virgin Islands, Saint Martin, Puerto Rico
Inside
$1,069
Oceanview
$1,309
Balcony
$1,429
Suite
$5,268
From
US$1,069
Per Person
View Trip
Cruise
 (1)

14 Days (13 Nights) New York to Miami
Cruise Line: Norwegian Cruise Line
Departure: 24 October 2026
Visit: USA, Bermuda, Puerto Rico, Virgin Islands (+4 more), Curacao, Aruba, Dominican Republic, Bahamas
Inside
$1,479
Oceanview
$1,579
Balcony
$2,889
Suite
$4,719
From
US$1,479
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Departures: May 2026 to Mar 2028
Visit: Colombia, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$943
Oceanview
$1,053
Balcony
$1,362
Suite
$1,511
From
US$943
Save 1,475
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
$849
Oceanview
$949
Balcony
$1,149
Suite
$2,399
From
US$849
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departure: 31 October 2027
Visit: USA, Jamaica, Colombia, Panama (+7 more), Costa Rica, Honduras, Belize, Bonaire, Aruba, Dominican Republic, Cayman Islands
Inside
$2,031
Oceanview
$2,251
Balcony
$2,801
Suite
-
From
US$2,031
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$829
Oceanview
$1,209
Balcony
$1,169
Suite
$1,319
From
US$829
Per Person
View Trip
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departure: 03 October 2027
Visit: USA, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$768
Oceanview
$936
Balcony
$965
Suite
$3,445
From
US$768
Save 441
Per Person
View Trip
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
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Inside
$399
Oceanview
$519
Balcony
$601
Suite
$1,461
From
US$399
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$439
Oceanview
$569
Balcony
$799
Suite
$879
From
US$439
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
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,473
From
US$674
Save 552
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$987
Oceanview
$987
Balcony
$1,199
Suite
$3,049
From
US$987
Save 553
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 17 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$559
Oceanview
-
Balcony
$854
Suite
$999
From
US$559
Per Person
View Trip
Cruise
 (3)

17 Days (16 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Departure: 29 October 2026
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$3,659
Oceanview
$4,219
Balcony
$5,509
Suite
-
From
US$3,659
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
$742
Oceanview
$990
Balcony
$1,174
Suite
$1,654
From
US$980
Save 520
Per Person
View Trip
Cruise
 (4)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: 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
-
Oceanview
$1,799
Balcony
$2,299
Suite
-
From
US$1,799
Per Person
View Trip
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$594
Oceanview
$644
Balcony
$719
Suite
$1,249
From
US$594
Per Person
View Trip
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
$1,434
Balcony
$1,614
Suite
$2,994
From
US$1,434
Per Person
View Trip
Cruise
 (3)

12 Days (11 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Nov 2026 to Mar 2028
Visit: USA, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Drinks & WiFi Package
Inside
$943
Oceanview
$1,063
Balcony
$1,363
Suite
$4,583
From
US$943
Per Person
View Trip
Cruise
 (1)

20 Days (19 Nights) New York to Santiago
Cruise Line: Viking Cruises
Departures: Oct 2026 to Oct 2029
Visit: USA, Bahamas, Jamaica, Panama, Peru, Chile
Flights Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,995
Suite
$14,995
From
US$8,995
Save 2,000
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departure: 22 October 2027
Visit: USA, Mexico, Bahamas
Inside
$779
Oceanview
$909
Balcony
$1,109
Suite
$1,279
From
US$779
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
Drinks & WiFi Package
Inside
$358
Oceanview
$428
Balcony
$609
Suite
$2,249
From
US$358
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
$911
Oceanview
$1,013
Balcony
$1,196
Suite
$2,957
From
US$911
Save 698
Per Person
View Trip
Results: 31-60 of 191

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Routes

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 Buenos Aires to Santiago Cruises from Cartagena to Cartagena Cruises from Colon to Colon Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Fort Lauderdale 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 Rome 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 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 Panama City to Miami Cruises from Paris to Paris Cruises from Philadelphia to Philadelphia Cruises from Philipsburg to Bridgetown 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 Buenos Aires 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 Francisco to San Francisco 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 Seattle Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Vancouver to Los Angeles Cruises from Vancouver to Seattle Cruises from Venice to Barcelona Cruises from Venice to Rome

Country Routes

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