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

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191 Cruises (1,786 Cruise Departures)
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 30 October 2027
Visit: USA, Turks and Caicos Islands, Curacao, Aruba, Bonaire
Exclusive Savings
Inside
$1,403
Oceanview
$1,687
Balcony
$1,860
Suite
$4,606
From
US$1,403
Save 832
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: May 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas
Inside
$597
Oceanview
$838
Balcony
$978
Suite
$1,458
From
US$597
Per Person
View Trip
Cruise

9 Days (8 Nights) Halifax to Bridgetown
Cruise Line: Seabourn
Departures: Oct 2026 to Oct 2028
Visit: Canada, Saint Kitts and Nevis, Spain, Saint Lucia, Barbados
Inside
-
Oceanview
-
Balcony
-
Suite
$5,198
From
US$5,198
Per Person
View Trip
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Aug 2027
Visit: USA, Cayman Islands, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,055
Oceanview
$1,155
Balcony
$1,407
Suite
$4,265
From
US$1,055
Save 743
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Inside
$1,154
Oceanview
$1,501
Balcony
$1,854
Suite
$3,591
From
US$1,154
Per Person
View Trip
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$711
Oceanview
$887
Balcony
$1,012
Suite
$1,981
From
US$711
Per Person
View Trip
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$459
Oceanview
$554
Balcony
$696
Suite
$1,205
From
US$459
Save 393
Per Person
View Trip
New ReleaseCruise

9 Days (8 Nights) Saint John's to Bridgetown
Cruise Line: Scenic
Departure: 15 October 2027
Visit: Antigua and Barbuda, Saint Barthelemy, Virgin Islands, Montserrat (+5 more), Martinique, Saint Lucia, Saint Vincent, Trinidad and Tobago, Barbados
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,463
Suite
$8,021
From
US$6,463
Save 1,872
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 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
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Dec 2026
Visit: USA, Mexico, Bahamas
Exclusive Savings
Inside
$518
Oceanview
$739
Balcony
$1,125
Suite
$1,208
From
US$781
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,388
Oceanview
$1,529
Balcony
$1,682
Suite
$2,680
From
US$1,489
Save 1,043
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to Miami
Cruise Line: Royal Caribbean
Departure: 28 October 2027
Visit: USA, Bermuda, Aruba, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$940
Balcony
$1,320
Suite
$2,385
From
US$840
Save 417
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
$907
Oceanview
$1,383
Balcony
$1,023
Suite
$3,110
From
US$990
Save 563
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Apr 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,463
Oceanview
$1,763
Balcony
$1,875
Suite
$3,400
From
US$2,126
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Jun 2027 to Nov 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$659
Oceanview
$749
Balcony
$1,199
Suite
$1,496
From
US$659
Save 507
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 30 October 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Inside
$1,461
Oceanview
$2,014
Balcony
$2,220
Suite
$3,751
From
US$1,461
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 25 October 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Saint Martin, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Anguilla
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$9,075
From
US$9,075
Per Person
View Trip
Cruise

26 Days (25 Nights) Montreal to Miami
Cruise Line: Silversea
Departure: 24 October 2026
Visit: Canada, USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Montserrat
All-Inclusive Fare
Inside
-
Oceanview
$9,500
Balcony
$12,000
Suite
$21,000
From
US$9,500
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
$749
Oceanview
$929
Balcony
$1,024
Suite
$1,399
From
US$749
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,421
Oceanview
$1,544
Balcony
$1,714
Suite
$2,955
From
US$1,484
Save 913
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Departures: Oct 2026 to Dec 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,095
From
US$4,095
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: MSC Cruises
Ship: MSC Seascape
Departures: May 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Drinks & WiFi Package
Inside
$393
Oceanview
$519
Balcony
$565
Suite
$1,195
From
US$393
Per Person
View Trip
Cruise

5 Days (4 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$430
Oceanview
$538
Balcony
$651
Suite
$1,001
From
US$449
Save 423
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Sep 2026 to Apr 2028
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$873
Oceanview
$995
Balcony
$1,187
Suite
$3,014
From
US$873
Save 769
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,152
Oceanview
$1,581
Balcony
$1,439
Suite
$3,744
From
US$1,655
Save 50
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Oct 2027 to Oct 2027
Visit: USA, Bahamas, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$826
Oceanview
$916
Balcony
$945
Suite
$2,000
From
US$826
Save 439
Per Person
View Trip
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Barbados, Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin, Antigua and Barbuda
Drinks & WiFi Package
Inside
$1,448
Oceanview
$1,748
Balcony
$2,738
Suite
$3,898
From
US$1,448
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Nov 2027
Visit: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,159
Oceanview
$1,311
Balcony
$1,508
Suite
$3,758
From
US$1,159
Save 695
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2027
Visit: USA, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,166
Oceanview
$1,306
Balcony
$1,346
Suite
$2,940
From
US$1,166
Save 723
Per Person
View Trip
New ReleaseCruise

12 Days (11 Nights) Miami to Panama City
Cruise Line: Scenic
Departure: 13 October 2028
Visit: USA, Bahamas, Colombia, Panama
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,683
Suite
$17,554
From
US$9,683
Save 2,412
Per Person
View Trip
Results: 151-180 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