Caribbean Cruises Starting In October 2027, 2028 and 2029

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152 Cruises (1,773 Departures)
152 Cruises (1,773 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$300pp
$191,550pp
Countries
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Cruise
 (3)

14 Days (13 Nights) Tokyo to Tokyo
Operator: Celebrity Cruises
Departure: 16 October 2028
Visits: Japan, South Korea
Exclusive Savings
Inside
$2,421
Oceanview
$3,270
Balcony
$4,522
Suite
$10,954
From (Per Person)
A$2,421
Save 1,687
Per Person
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Departure: 14 October 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$1,019
Oceanview
$1,145
Balcony
$1,782
Suite
$2,901
From (Per Person)
A$1,019
Save 603
Per Person
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Departures: Oct 2027 to Feb 2029
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$895
Oceanview
$988
Balcony
$1,033
Suite
$1,508
From (Per Person)
A$895
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Departures: Dec 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,528
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
Per Person
Cruise
 (13)

31 Days (30 Nights) Barcelona to Miami
Operator: Cunard
Departure: 31 October 2028
Visits: Spain, Portugal, USA, Virgin Islands +5 more, Saint Martin, Antigua and Barbuda, Dominica, Barbados, Saint Kitts and Nevis
Exclusive Savings
Inside
$3,772
Oceanview
$4,811
Balcony
$5,800
Suite
$16,147
From (Per Person)
A$3,772
Per Person
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2027 to Dec 2027
Visits: USA, Bonaire, Aruba, Curacao +7 more, Dominican Republic, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Exclusive Savings
Inside
$3,459
Oceanview
-
Balcony
$4,558
Suite
-
From (Per Person)
A$3,459
Per Person
Cruise
 (13)

28 Days (27 Nights) Barcelona to Miami
Operator: Cunard
Departure: 29 October 2027
Visits: Spain, USA, Virgin Islands, Saint Kitts and Nevis +4 more, Grenada, Barbados, Saint Lucia, Saint Martin
Exclusive Savings
Inside
$6,038
Oceanview
$6,909
Balcony
$8,552
Suite
$20,600
From (Per Person)
A$6,038
Per Person
Cruise
 (6)

10 Days (9 Nights) New York to San Juan
Operator: Azamara
Departure: 28 October 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,835
Oceanview
$3,286
Balcony
$4,030
Suite
$6,902
From (Per Person)
A$2,835
Per Person
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2027 to Dec 2027
Visits: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Exclusive Savings
Inside
$1,589
Oceanview
$1,738
Balcony
$2,094
Suite
$7,293
From (Per Person)
A$1,589
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Departures: Dec 2026 to Apr 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$962
Oceanview
$1,395
Balcony
$1,171
Suite
$1,439
From (Per Person)
A$962
Save 22
Per Person
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$636
Oceanview
$774
Balcony
$1,022
Suite
$2,002
From (Per Person)
A$636
Save 16
Per Person
Cruise
 (5)

15 Days (14 Nights) London to Bridgetown
Ship: Iona
Departures: Oct 2027 to Oct 2028
Visits: England, Spain, Saint Martin, Dominica, Barbados
Bonus Onboard Spend
Exclusive Savings
Inside
$2,009
Oceanview
$2,573
Balcony
$2,751
Suite
$4,553
From (Per Person)
A$2,009
Per Person
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Departures: Nov 2026 to Oct 2027
Visits: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,641
Oceanview
$1,824
Balcony
$1,873
Suite
$5,280
From (Per Person)
A$1,641
Save 1,511
Per Person
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departure: 31 October 2027
Visits: USA, Jamaica, Colombia, Panama +7 more, Costa Rica, Honduras, Belize, Bonaire, Aruba, Dominican Republic, Cayman Islands
Exclusive Savings
Inside
$3,607
Oceanview
$3,934
Balcony
$4,756
Suite
-
From (Per Person)
A$3,607
Per Person
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$626
Oceanview
$764
Balcony
$982
Suite
$2,031
From (Per Person)
A$626
Save 51
Per Person
Cruise
 (1)

25 Days (24 Nights) Halifax to Rio de Janeiro
Operator: Seabourn
Departures: Oct 2027 to Oct 2028
Visits: Canada, Saint Kitts and Nevis, Spain, Saint Lucia +4 more, Barbados, Trinidad and Tobago, French Guiana, Brazil
Exclusive Savings
Balcony
-
Suite
$18,569
From (Per Person)
A$18,569
Save 357
Per Person
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Departures: Dec 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$935
Oceanview
$1,082
Balcony
$1,227
Suite
$2,677
From (Per Person)
A$935
Per Person
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Exclusive Savings
Inside
$964
Oceanview
$1,162
Balcony
$1,697
Suite
$2,498
From (Per Person)
A$964
Save 15
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departure: 31 October 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$2,257
Oceanview
$2,277
Balcony
$2,598
Suite
$4,304
From (Per Person)
A$2,257
Save 1,204
Per Person
Cruise

10 Days (9 Nights) New York to Miami
Operator: Royal Caribbean
Departure: 28 October 2027
Visits: USA, Bermuda, Aruba, Cayman Islands
Exclusive Savings
Inside
$1,293
Oceanview
$1,355
Balcony
$1,506
Suite
$3,233
From (Per Person)
A$1,293
Save 557
Per Person
Cruise

72 Days (71 Nights) Miami to Los Angeles
Operator: Oceania
Departure: 27 October 2028
Visits: USA, Virgin Islands, Saint Martin, Saint Barthelemy +20 more, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Martinique, Saint Lucia, Barbados, Saint Vincent, Grenada, French Guiana, Brazil, Uruguay, Argentina, Falkland Islands, Antarctica, Chile, Peru, Ecuador, Costa Rica, Guatemala, Mexico
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$52,131
From (Per Person)
A$52,131
Save 3,469
Per Person
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Departure: 30 October 2027
Visits: USA, Bahamas, Dominican Republic, Aruba, Curacao
Exclusive Savings
Inside
$1,905
Oceanview
$2,137
Balcony
$2,190
Suite
$4,276
From (Per Person)
A$1,905
Save 1,012
Per Person
New ReleaseCruise

24 Days (23 Nights) New York to Rio de Janeiro
Operator: Crystal
Departure: 12 October 2027
Visits: USA, Bermuda, Antigua and Barbuda, Guadeloupe +7 more, Saint Barthelemy, Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Trinidad and Tobago, French Guiana, Brazil
Exclusive Savings
Oceanview
$14,871
Balcony
$17,037
Suite
$18,255
From (Per Person)
A$14,139
Save 4,461
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,141
Oceanview
$1,587
Balcony
$1,587
Suite
$1,989
From (Per Person)
A$1,141
Save 22
Per Person
CruiseFlights Included

20 Days (19 Nights) New York to Santiago
Operator: Viking
Departures: Oct 2027 to Oct 2029
Visits: USA, Bahamas, Jamaica, Panama, Peru, Chile
Exclusive Savings
Balcony
$17,439
Suite
$24,299
From (Per Person)
A$17,439
Save 374
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: Aug 2027 to Oct 2028
Visits: USA, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,475
Oceanview
$1,740
Balcony
$1,677
Suite
$3,835
From (Per Person)
A$1,475
Save 1,396
Per Person
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Departures: Dec 2027 to Mar 2029
Visits: USA, Bahamas, Virgin Islands, Saint Martin
Sanctuary Collection
Exclusive Savings
Inside
$877
Oceanview
$1,093
Balcony
$1,335
Suite
$1,885
From (Per Person)
A$877
Per Person
Cruise

22 Days (21 Nights) Marseille to Fort-de-France
Operator: MSC Cruises
Departure: 30 October 2027
Visits: France, Italy, Sicily, Malta +5 more, Spain, Antigua and Barbuda, Saint Vincent, Barbados, Martinique
Exclusive Savings
Inside
$2,296
Oceanview
$2,731
Balcony
$3,543
Suite
$6,761
From (Per Person)
A$2,296
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Nov 2027 to Nov 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,408
Oceanview
$1,685
Balcony
$1,824
Suite
$2,398
From (Per Person)
A$1,408
Per Person
Cruise

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Departure: 07 October 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Dominica, Barbados
Exclusive Savings
Inside
$1,166
Oceanview
$1,292
Balcony
$2,067
Suite
$2,457
From (Per Person)
A$1,166
Save 680
Per Person
Results: 31-60 of 152

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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 Marigot Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Bridgetown to Philipsburg 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 Rome Cruises from Fort Lauderdale to San Juan 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 Miami Cruises from New York to Fort Lauderdale 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 Philadelphia to Philadelphia Cruises from Philipsburg to Philipsburg 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 London Cruises from Rio de Janeiro to Buenos Aires Cruises from Rio de Janeiro to Lisbon 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 Barcelona Cruises from Rome to Venice Cruises from Rome to Fort Lauderdale Cruises from Rome to Rome Cruises from San Juan to Fort Lauderdale 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 Tokyo Cruises from Singapore to Sydney Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Tokyo to Tokyo

Country Routes

Cruises from Peru to Argentina Cruises from USA to Portugal Cruises from USA to Germany Cruises from Italy to England Cruises from Dominican Republic to Puerto Rico Cruises from Greece to Portugal Cruises from France to Portugal Cruises from Germany to England Cruises from Canada to Japan Cruises from France to Spain Cruises from Portugal to England Cruises from Iceland to USA Cruises from Puerto Rico to USA Cruises from Iceland to France Cruises from Brazil to USA Cruises from Japan to China 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 Australia to Japan Cruises from England to Germany Cruises from Singapore to China Cruises from Brazil to Portugal Cruises from Puerto Rico to Dominican Republic 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 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 Japan 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 Singapore to Japan Cruises from Spain to France Cruises from Spain to Italy Cruises from Germany to USA 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 USA to Japan Cruises from Spain to England Cruises from USA to Panama Cruises from USA to Peru Cruises from USA to Spain Cruises from Japan to Canada