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

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Departure: 09 October 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$2,021
Oceanview
$1,856
Balcony
$2,576
Suite
$4,282
From (Per Person)
A$1,856
Save 975
Per Person
Cruise

9 Days (8 Nights) Miami to Miami
Operator: Royal Caribbean
Departure: 21 October 2028
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,746
Oceanview
$1,914
Balcony
$2,158
Suite
$3,904
From (Per Person)
A$1,746
Save 919
Per Person
Cruise

10 Days (9 Nights) San Juan to San Juan
Operator: Royal Caribbean
Departure: 29 October 2027
Visits: Puerto Rico, Aruba, Curacao, Barbados, Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$1,353
Oceanview
$1,465
Balcony
$2,155
Suite
$5,087
From (Per Person)
A$1,353
Save 763
Per Person
Cruise

11 Days (10 Nights) Boston to Fort Lauderdale
Operator: Royal Caribbean
Departure: 20 October 2028
Visits: USA, Bermuda, Aruba, Curacao
Exclusive Savings
Inside
$1,554
Oceanview
$1,761
Balcony
$2,150
Suite
$4,046
From (Per Person)
A$1,554
Save 752
Per Person
New ReleaseCruise

31 Days (30 Nights) New York to Buenos Aires
Operator: 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
$18,798
Balcony
$23,829
Suite
$24,702
From (Per Person)
A$18,798
Save 4,702
Per Person
Cruise

7 Days (6 Nights) Miami to Miami
Operator: Royal Caribbean
Departures: Jul 2028 to Oct 2028
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$1,286
Oceanview
$1,396
Balcony
$1,568
Suite
$2,842
From (Per Person)
A$1,286
Save 932
Per Person
New ReleaseCruise

15 Days (14 Nights) San Juan to Rio de Janeiro
Operator: Crystal
Departure: 21 October 2027
Visits: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Trinidad and Tobago, French Guiana, Brazil
Exclusive Savings
Oceanview
$9,662
Balcony
$12,551
Suite
$13,033
From (Per Person)
A$9,662
Save 3,838
Per Person
Cruise

10 Days (9 Nights) New York to Fort Lauderdale
Operator: Royal Caribbean
Departure: 31 October 2027
Visits: USA, Aruba, Curacao
Exclusive Savings
Inside
$1,328
Oceanview
$1,448
Balcony
$1,537
Suite
$3,696
From (Per Person)
A$1,328
Save 754
Per Person
New ReleaseCruise

12 Days (11 Nights) Tenerife to Saint John's
Operator: Scenic
Departure: 04 October 2027
Visits: Spain, Saint Martin, Saint Barthelemy, Antigua and Barbuda
Exclusive Savings
Balcony
$8,266
Suite
$9,320
From (Per Person)
A$8,266
Save 4,149
Per Person
Cruise

8 Days (7 Nights) Galveston to Galveston
Operator: MSC Cruises
Ship: MSC Seascape
Departures: Nov 2026 to Nov 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$546
Oceanview
$715
Balcony
$814
Suite
$1,546
From (Per Person)
A$546
Save 12
Per Person
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Departures: Nov 2026 to Oct 2028
Visits: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,718
Oceanview
$2,005
Balcony
$2,072
Suite
$3,927
From (Per Person)
A$1,718
Save 1,769
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: May 2027 to Oct 2028
Visits: USA, Bahamas, Dominican Republic, Virgin Islands
Exclusive Savings
Inside
$1,995
Oceanview
$2,264
Balcony
$2,335
Suite
$4,529
From (Per Person)
A$1,995
Save 1,422
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Operator: Regent Seven Seas
Departure: 28 October 2028
Visits: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Balcony
$8,224
Suite
$9,956
From (Per Person)
A$8,224
Save 6,796
Per Person
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Departure: 10 October 2027
Visits: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$991
Oceanview
$1,377
Balcony
$1,342
Suite
$4,452
From (Per Person)
A$991
Save 698
Per Person
Cruise

10 Days (9 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: May 2027 to Oct 2027
Visits: USA, Curacao, Bonaire, Aruba, Bahamas
Exclusive Savings
Inside
$1,394
Oceanview
$1,647
Balcony
$2,419
Suite
$3,942
From (Per Person)
A$1,394
Save 994
Per Person
Cruise

29 Days (28 Nights) Miami to Miami
Operator: 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
Exclusive Savings
Inside
$6,009
Oceanview
$6,772
Balcony
$10,613
Suite
$13,682
From (Per Person)
A$6,009
Per Person
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Departures: Jan 2028 to Oct 2028
Visits: USA, Bahamas, Mexico, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$2,755
Oceanview
$3,310
Balcony
$3,607
Suite
$6,656
From (Per Person)
A$2,755
Per Person
Cruise

6 Days (5 Nights) Tampa to Tampa
Operator: Royal Caribbean
Departures: Nov 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$567
Oceanview
$615
Balcony
$667
Suite
$1,395
From (Per Person)
A$567
Save 1,003
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Departures: Jun 2027 to Oct 2028
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,329
Oceanview
$1,454
Balcony
$1,474
Suite
$3,060
From (Per Person)
A$1,329
Save 1,117
Per Person
Cruise

15 Days (14 Nights) Miami to Miami
Operator: MSC Cruises
Departures: Dec 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Exclusive Savings
Inside
$2,369
Oceanview
$2,874
Balcony
$2,983
Suite
$4,587
From (Per Person)
A$2,369
Per Person
Cruise

15 Days (14 Nights) La Romana to La Romana
Operator: 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
$2,224
Oceanview
$2,670
Balcony
$3,828
Suite
$5,669
From (Per Person)
A$2,224
Per Person
Cruise

15 Days (14 Nights) La Romana to La Romana
Operator: MSC Cruises
Ship: MSC Opera
Departures: Jun 2027 to Oct 2028
Visits: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda, Barbados, Guadeloupe
Exclusive Savings
Inside
$2,224
Oceanview
$2,680
Balcony
$3,828
Suite
$5,669
From (Per Person)
A$2,224
Save 51
Per Person
New ReleaseCruise

10 Days (9 Nights) New York to San Juan
Operator: Crystal
Departure: 12 October 2027
Visits: USA, Bermuda, Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Puerto Rico
Exclusive Savings
Oceanview
$5,776
Balcony
$6,550
Suite
$6,894
From (Per Person)
A$5,458
Save 1,742
Per Person
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Departures: Jan 2028 to Mar 2029
Visits: USA, Bahamas, Virgin Islands, Saint Martin, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Exclusive Savings
Inside
$2,155
Oceanview
$2,286
Balcony
$3,058
Suite
$4,243
From (Per Person)
A$2,155
Per Person
Cruise

14 Days (13 Nights) New York to Miami
Operator: Silversea
Departure: 21 October 2028
Visits: USA, Bermuda, Virgin Islands, Saint Barthelemy, Aruba
Exclusive Savings
Oceanview
$6,835
Balcony
$7,864
Suite
$7,019
From (Per Person)
A$6,835
Save 2,465
Per Person
Cruise

10 Days (9 Nights) San Juan to San Juan
Operator: Celebrity Cruises
Departure: 29 October 2027
Visits: Puerto Rico, Antigua and Barbuda, Saint Lucia, Grenada, Barbados, Saint Vincent, Virgin Islands
Exclusive Savings
Inside
$1,293
Oceanview
$1,313
Balcony
$1,760
Suite
$6,651
From (Per Person)
A$1,293
Save 925
Per Person
Cruise

11 Days (10 Nights) Boston to Miami
Operator: Celebrity Cruises
Departure: 19 October 2028
Visits: USA, Aruba, Curacao, Turks and Caicos Islands
Exclusive Savings
Inside
$1,559
Oceanview
$1,957
Balcony
$1,899
Suite
$8,307
From (Per Person)
A$1,559
Save 1,026
Per Person
Cruise

13 Days (12 Nights) Miami to Bridgetown
Operator: Oceania
Departure: 27 October 2028
Visits: USA, Virgin Islands, Saint Martin, Saint Barthelemy +6 more, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Martinique, Saint Lucia, Barbados
Your World Inclusions
Exclusive Savings
Inside
$4,890
Oceanview
$5,579
Balcony
$8,023
Suite
$9,061
From (Per Person)
A$4,890
Save 2,130
Per Person
Cruise

6 Days (5 Nights) Orlando to Orlando
Operator: Princess
Departures: Oct 2027 to Mar 2028
Visits: USA, Bahamas, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$676
Oceanview
$924
Balcony
$963
Suite
$1,369
From (Per Person)
A$676
Per Person
Cruise

7 Days (6 Nights) Galveston to Galveston
Operator: Royal Caribbean
Departures: Oct 2027 to Oct 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,168
Oceanview
$1,339
Balcony
$1,565
Suite
$2,658
From (Per Person)
A$1,168
Save 1,010
Per Person
Results: 121-150 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