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

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213 Cruises (1,912 Departures)
213 Cruises (1,912 Departures)
Departures
Duration
5 Days
46 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$400pp
$205,420pp
Countries
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New ReleaseCruise

12 Days (11 Nights) Bridgetown to Panama City
Cruise Line: Scenic
Departure: 20 October 2027
Visits: Barbados, Saint Lucia, Saint Vincent, Curacao, Colombia, Panama
Exclusive Savings
Balcony
$12,639
Suite
$15,329
From (Per Person)
A$12,639
Save 4,206
Per Person
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 25 October 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe +5 more, Saint Martin, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Anguilla
Exclusive Savings
Suite
$16,077
From (Per Person)
A$16,077
Save 328
Per Person
New ReleaseCruise

15 Days (14 Nights) San Juan to Rio de Janeiro
Cruise Line: Crystal
Departure: 21 October 2027
Visits: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Trinidad and Tobago, French Guiana, Brazil
Exclusive Savings
Oceanview
$10,191
Balcony
$13,260
Suite
$13,674
From (Per Person)
A$10,191
Save 2,109
Per Person
Cruise

28 Days (27 Nights) Barcelona to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 October 2026
Visits: Spain, Portugal, Morocco, Antigua and Barbuda, Anguilla, Puerto Rico, USA
Exclusive Savings
Suite
$21,790
From (Per Person)
A$21,790
Save 445
Per Person
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Nov 2026 to Nov 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Exclusive Savings
Inside
$1,103
Oceanview
$1,330
Balcony
$1,904
Suite
$2,825
From (Per Person)
A$1,103
Per Person
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,661
Oceanview
$1,734
Balcony
$2,078
Suite
$6,287
From (Per Person)
A$1,661
Save 822
Per Person
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2027
Visits: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,584
Oceanview
$1,911
Balcony
$1,940
Suite
$6,332
From (Per Person)
A$1,584
Save 1,147
Per Person
Cruise

13 Days (12 Nights) Orlando to Fort Lauderdale
Cruise Line: Princess
Departure: 18 October 2026
Visits: USA, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,487
Oceanview
$1,566
Balcony
$2,125
Suite
$3,540
From (Per Person)
A$1,487
Per Person
Cruise

15 Days (14 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2028 to Oct 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,214
Oceanview
$2,670
Balcony
$3,858
Suite
$5,660
From (Per Person)
A$2,214
Per Person
Cruise

7 Days (6 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Apr 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,227
Oceanview
$1,360
Balcony
$1,396
Suite
$4,389
From (Per Person)
A$1,227
Save 877
Per Person
Cruise

11 Days (10 Nights) New York to Miami
Cruise Line: Royal Caribbean
Departure: 29 October 2026
Visits: USA, Dominican Republic, Aruba, Curacao
Exclusive Savings
Inside
$1,555
Oceanview
$1,636
Balcony
$2,336
Suite
-
From (Per Person)
A$1,555
Save 576
Per Person
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,509
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$1,509
Per Person
Cruise

46 Days (45 Nights) Rome to Los Angeles
Cruise Line: Oceania
Departure: 19 October 2028
Visits: Italy, Sicily, Malta, Tunisia +12 more, Sardinia, Spain, Portugal, Puerto Rico, USA, Cayman Islands, Colombia, Panama, Costa Rica, Nicaragua, Guatemala, Mexico
Your World Inclusions
Exclusive Savings
Balcony
$27,393
Suite
$37,947
From (Per Person)
A$27,393
Save 2,787
Per Person
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Departure: 14 October 2027
Visits: USA, Canada
Exclusive Savings
Inside
$2,026
Oceanview
$2,439
Balcony
$3,441
Suite
$7,763
From (Per Person)
A$2,026
Save 743
Per Person
New ReleaseCruise

27 Days (26 Nights) Montreal to Fort Lauderdale
Cruise Line: Crystal
Departure: 16 October 2026
Visits: Canada, USA, Bermuda, Dominican Republic +4 more, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Oceanview
$20,145
Balcony
$28,900
Suite
$29,325
From (Per Person)
A$20,145
Save 2,955
Per Person
Cruise

5 Days (4 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Jul 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$745
Oceanview
$846
Balcony
$1,015
Suite
$1,831
From (Per Person)
A$745
Save 645
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jun 2027 to Oct 2027
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,729
Oceanview
$1,824
Balcony
$1,993
Suite
$6,246
From (Per Person)
A$1,729
Save 993
Per Person
Cruise

15 Days (14 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda, Barbados, Guadeloupe
Exclusive Savings
Inside
$2,234
Oceanview
$2,690
Balcony
$3,838
Suite
$5,679
From (Per Person)
A$2,234
Save 50
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 23 October 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,689
Oceanview
$1,894
Balcony
$1,989
Suite
$5,899
From (Per Person)
A$1,689
Save 669
Per Person
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 29 October 2027
Visits: Puerto Rico, Aruba, Curacao, Barbados, Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$1,611
Oceanview
$1,721
Balcony
$2,697
Suite
$7,251
From (Per Person)
A$1,611
Save 630
Per Person
New ReleaseCruise

31 Days (30 Nights) New York to Buenos Aires
Cruise Line: Crystal
Departure: 12 October 2027
Visits: USA, Bermuda, Antigua and Barbuda, Guadeloupe +9 more, Saint Barthelemy, Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Trinidad and Tobago, French Guiana, Brazil, Uruguay, Argentina
Exclusive Savings
Oceanview
$18,252
Balcony
$24,030
Suite
$24,732
From (Per Person)
A$18,252
Save 3,648
Per Person
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 30 October 2027
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Exclusive Savings
Inside
$2,498
Oceanview
$3,389
Balcony
$3,745
Suite
$5,884
From (Per Person)
A$2,498
Per Person
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 31 October 2026
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,305
Oceanview
$1,438
Balcony
$2,116
Suite
$6,530
From (Per Person)
A$1,305
Save 466
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,143
Oceanview
$1,311
Balcony
$1,529
Suite
$2,083
From (Per Person)
A$1,143
Per Person
Cruise

29 Days (28 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 30 October 2027
Visits: USA, Bahamas, Jamaica, Dominican Republic +12 more, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Curacao, Aruba, Colombia, Panama, Costa Rica, Belize, Mexico
Fare Saver
Exclusive Savings
Inside
$6,009
Oceanview
$6,772
Balcony
$10,613
Suite
$13,682
From (Per Person)
A$6,009
Per Person
Cruise

21 Days (20 Nights) Los Angeles to New York
Cruise Line: Norwegian Cruise Line
Departure: 19 October 2027
Visits: USA, Mexico, Guatemala, Costa Rica +4 more, Panama, Colombia, Jamaica, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$4,487
Oceanview
$5,678
Balcony
$6,794
Suite
$7,687
From (Per Person)
A$4,487
Per Person
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: Nov 2026 to Oct 2027
Visits: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,817
Oceanview
$1,842
Balcony
$2,350
Suite
$5,840
From (Per Person)
A$1,817
Save 1,343
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Apr 2027
Visits: USA, Bahamas, Mexico, Honduras
Exclusive Savings
Inside
$2,232
Oceanview
$2,311
Balcony
$2,476
Suite
$5,007
From (Per Person)
A$2,232
Save 1,061
Per Person
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 30 October 2026
Visits: USA, Mexico, Bahamas
Exclusive Savings
Inside
$1,005
Oceanview
$1,259
Balcony
$1,322
Suite
$5,524
From (Per Person)
A$1,005
Save 362
Per Person
Cruise

17 Days (16 Nights) Florence to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 31 October 2026
Visits: Italy, France, Spain, Morocco +4 more, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominican Republic
Exclusive Savings
Inside
$1,839
Oceanview
$2,245
Balcony
$4,136
Suite
$5,621
From (Per Person)
A$1,839
Per Person
Results: 121-150 of 213

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Routes

Cruises from Athens to Lisbon Cruises from Athens to Barcelona Cruises from Athens to Rome Cruises from Athens to Venice Cruises from Baltimore to Baltimore Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to Lisbon Cruises from Barcelona to London Cruises from Barcelona to Rome Cruises from Barcelona to Venice Cruises from Barcelona to Barcelona Cruises from Barcelona to Miami Cruises from Boston to Boston Cruises from Bridgetown to San Juan 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 Los Angeles Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Barcelona Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort Lauderdale to San Diego 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 Miami 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 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 Quebec City to New York Cruises from Reykjavik to New York Cruises from Reykjavik to London 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 London Cruises from Rome to Lisbon Cruises from Rome to Miami Cruises from Rome to Barcelona Cruises from Rome to Venice Cruises from Rome to Fort Lauderdale Cruises from Rome to Rome Cruises from San Diego to Fort Lauderdale Cruises from San Diego to San Diego Cruises from San Francisco to San Francisco Cruises from San Juan to Bridgetown 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 Sydney Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Vancouver to Los Angeles Cruises from Vancouver to Seattle Cruises from Vancouver to San Diego

Country Routes

Cruises from Peru to Argentina Cruises from Australia to England Cruises from Barbados to Puerto Rico Cruises from USA to Portugal Cruises from USA to Germany Cruises from Italy to England Cruises from Greece 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 Barbados Cruises from Puerto Rico to USA Cruises from Portugal to France Cruises from Chile to USA Cruises from France to Brazil Cruises from Brazil to France 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 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 Australia 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 Italy Cruises from England to Spain Cruises from England to USA Cruises from France to Italy Cruises from Saint Martin to Barbados Cruises from Greece to Italy Cruises from Greece to Spain 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 Greece to USA Cruises from Portugal to USA Cruises from Singapore to Australia 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 Australia 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