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

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213 Cruises (1,914 Departures)
213 Cruises (1,914 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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Cruise

15 Days (14 Nights) London to Bridgetown
Cruise Line: P&O Cruises Worldwide
Ship: Arvia
Departures: Oct 2026 to Oct 2027
Visits: England, Spain, Sint Maarten, Saint Kitts and Nevis, Saint Lucia, Barbados
Bonus Onboard Spend
Exclusive Savings
Inside
$2,089
Oceanview
$2,677
Balcony
$3,023
Suite
$4,736
From (Per Person)
A$2,089
Per Person
Cruise

25 Days (24 Nights) Lisbon to Miami
Cruise Line: Regent Seven Seas
Departure: 14 October 2028
Visits: Portugal, Spain, Bahamas, USA +5 more, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Balcony
$14,557
Suite
$17,731
From (Per Person)
A$14,557
Save 10,323
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

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,023
Oceanview
$1,448
Balcony
$1,912
Suite
$5,717
From (Per Person)
A$1,212
Save 477
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: Princess
Departures: Sep 2026 to Oct 2026
Visits: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$865
Oceanview
$934
Balcony
$1,750
Suite
$2,182
From (Per Person)
A$865
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 627
Per Person
Cruise

9 Days (8 Nights) Halifax to Bridgetown
Cruise Line: Seabourn
Departures: Oct 2026 to Oct 2028
Visits: Canada, Saint Kitts and Nevis, Spain, Saint Lucia, Barbados
Exclusive Savings
Balcony
-
Suite
$6,091
From (Per Person)
A$6,091
Save 133
Per Person
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Jul 2026 to Sep 2027
Visits: USA, Mexico
Exclusive Savings
Inside
$733
Oceanview
$818
Balcony
$1,001
Suite
$2,082
From (Per Person)
A$845
Save 789
Per Person
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

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Aug 2026 to Oct 2026
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,326
Oceanview
$1,673
Balcony
$2,108
Suite
$4,445
From (Per Person)
A$1,326
Per Person
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$836
Oceanview
$953
Balcony
$1,203
Suite
$2,109
From (Per Person)
A$836
Save 529
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

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Dec 2026 to Oct 2027
Visits: USA, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$835
Oceanview
$886
Balcony
$1,137
Suite
$1,873
From (Per Person)
A$835
Save 397
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
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: May 2027 to Dec 2027
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,216
Oceanview
$1,329
Balcony
$1,999
Suite
$4,032
From (Per Person)
A$1,216
Save 662
Per Person
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Nov 2028
Visits: Martinique, Antigua and Barbuda, Dominican Republic, Barbados
Exclusive Savings
Inside
$1,103
Oceanview
$1,330
Balcony
$1,904
Suite
$2,825
From (Per Person)
A$1,103
Per Person
New ReleaseCruise

11 Days (10 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Departure: 10 October 2027
Visits: Bahamas, Turks and Caicos Islands, Virgin Islands, Saint Barthelemy, Martinique, Saint Vincent, Barbados
Exclusive Savings
Balcony
$11,295
Suite
$12,716
From (Per Person)
A$11,295
Save 3,200
Per Person
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 24 October 2026
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,067
Oceanview
$1,285
Balcony
$1,521
Suite
$5,601
From (Per Person)
A$1,067
Save 384
Per Person
Cruise

25 Days (24 Nights) Halifax to Rio de Janeiro
Cruise Line: Seabourn
Departures: Oct 2026 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
$15,026
From (Per Person)
A$15,026
Save 354
Per Person
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jul 2026 to Oct 2026
Visits: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$2,239
Oceanview
$2,381
Balcony
$2,630
Suite
$6,958
From (Per Person)
A$2,239
Save 3,250
Per Person
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Departures: Oct 2026 to Dec 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$6,390
From (Per Person)
A$6,390
Save 141
Per Person
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Nov 2027
Visits: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,852
Oceanview
$2,027
Balcony
$2,137
Suite
$6,476
From (Per Person)
A$1,852
Save 1,071
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

10 Days (9 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 22 October 2027
Visits: USA, Bahamas, Dominican Republic, Haiti, Turks and Caicos Islands
Exclusive Savings
Inside
$1,905
Oceanview
$2,030
Balcony
$2,797
Suite
$5,314
From (Per Person)
A$1,905
Save 753
Per Person
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 22 October 2026
Visits: USA, Bahamas, Dominican Republic, Curacao, Aruba
Exclusive Savings
Inside
$1,471
Oceanview
$1,660
Balcony
$2,066
Suite
-
From (Per Person)
A$1,471
Save 544
Per Person
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,296
Oceanview
$1,405
Balcony
$2,582
Suite
$5,648
From (Per Person)
A$1,296
Save 491
Per Person
Cruise

11 Days (10 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Departure: 22 October 2026
Visits: USA, Turks and Caicos Islands, Saint Martin, Dominica +4 more, Martinique, Antigua and Barbuda, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$11,917
From (Per Person)
A$11,917
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

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2027 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Virgin Islands
Exclusive Savings
Inside
$2,343
Oceanview
$2,436
Balcony
$2,732
Suite
$7,459
From (Per Person)
A$2,343
Save 1,448
Per Person
Results: 151-180 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 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