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

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58 Days
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191 Cruises (1,786 Cruise Departures)
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$531
Oceanview
$581
Balcony
$824
Suite
$1,091
From
US$531
Per Person
View Trip
Cruise

19 Days (18 Nights) Rome to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 29 October 2026
Visit: Italy, France, Spain, Morocco (+4 more), Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominican Republic
Inside
$1,016
Oceanview
$1,458
Balcony
$2,353
Suite
$3,909
From
US$1,016
Per Person
View Trip
Cruise

26 Days (25 Nights) Rome to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 29 October 2026
Visit: Italy, France, Spain, Morocco (+8 more), Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Inside
-
Oceanview
$2,536
Balcony
$3,781
Suite
$5,917
From
US$2,536
Per Person
View Trip
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 31 October 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$872
Oceanview
$1,157
Balcony
$1,450
Suite
$2,563
From
US$1,276
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,462
Oceanview
$1,795
Balcony
$1,827
Suite
$2,770
From
US$1,462
Save 781
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: Jun 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Inside
$1,160
Oceanview
$1,511
Balcony
$1,911
Suite
$3,591
From
US$1,160
Per Person
View Trip
Cruise

18 Days (17 Nights) Quebec City to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 October 2026
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$9,240
From
US$9,240
Per Person
View Trip
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Aug 2027 to Nov 2027
Visit: USA, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,727
Oceanview
$1,874
Balcony
$2,018
Suite
$3,328
From
US$1,727
Save 871
Per Person
View Trip
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 29 October 2027
Visit: Puerto Rico, Aruba, Curacao, Barbados, Dominica, Antigua and Barbuda, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$874
Oceanview
$956
Balcony
$1,627
Suite
$1,802
From
US$1,292
Save 50
Per Person
View Trip
Cruise

5 Days (4 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2027
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$351
Oceanview
$381
Balcony
$464
Suite
$904
From
US$362
Save 628
Per Person
View Trip
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 30 October 2026
Visit: USA, Mexico, Bahamas
Exclusive Savings
Inside
$660
Oceanview
$800
Balcony
$1,062
Suite
$1,877
From
US$660
Save 383
Per Person
View Trip
Cruise

11 Days (10 Nights) Boston to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 20 October 2026
Visit: USA, Curacao, Bonaire, Aruba
Exclusive Savings
Inside
$1,243
Oceanview
-
Balcony
$1,391
Suite
$8,346
From
US$1,243
Save 790
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Aug 2026 to Mar 2027
Visit: USA, Mexico, Cayman Islands, Bahamas
Exclusive Savings
Inside
$795
Oceanview
$880
Balcony
$883
Suite
$2,586
From
US$802
Save 448
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, Curacao, Aruba, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,098
Oceanview
$1,244
Balcony
$1,345
Suite
$2,954
From
US$1,098
Save 852
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 23 October 2027
Visit: USA, Bahamas, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$967
Oceanview
$1,117
Balcony
$1,146
Suite
$2,420
From
US$967
Save 510
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$916
Oceanview
$1,067
Balcony
$1,096
Suite
$2,175
From
US$916
Save 1,368
Per Person
View Trip
Cruise

7 Days (6 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Nov 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$482
Oceanview
$522
Balcony
$684
Suite
$1,398
From
US$737
Save 435
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2026
Visit: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,318
Oceanview
$1,587
Balcony
$1,774
Suite
$2,933
From
US$1,563
Save 796
Per Person
View Trip
Cruise

11 Days (10 Nights) Boston to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 16 October 2027
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$952
Oceanview
$1,119
Balcony
$1,436
Suite
$5,027
From
US$1,110
Save 366
Per Person
View Trip
New ReleaseCruise

12 Days (11 Nights) Bridgetown to Panama City
Cruise Line: Scenic
Departure: 20 October 2027
Visit: Barbados, Saint Lucia, Saint Vincent, Curacao, Colombia, Panama
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,863
Suite
$12,090
From
US$9,863
Save 2,567
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 22 October 2026
Visit: USA, Bahamas, Dominican Republic, Curacao, Aruba
Exclusive Savings
Inside
$922
Oceanview
$1,132
Balcony
$1,404
Suite
$2,149
From
US$1,348
Save 50
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Departure: 14 October 2027
Visit: USA, Canada
Bonus Onboard Credit
Exclusive Savings
Inside
$1,026
Oceanview
$1,287
Balcony
$1,899
Suite
$2,854
From
US$1,026
Save 485
Per Person
View Trip
Cruise

11 Days (10 Nights) New York to Miami
Cruise Line: Royal Caribbean
Departure: 29 October 2026
Visit: USA, Dominican Republic, Aruba, Curacao
Exclusive Savings
Inside
$1,103
Oceanview
$1,466
Balcony
$1,656
Suite
$3,230
From
US$1,603
Save 50
Per Person
View Trip
Cruise

25 Days (24 Nights) Halifax to Rio de Janeiro
Cruise Line: Seabourn
Departures: Oct 2026 to Oct 2028
Visit: Canada, Saint Kitts and Nevis, Spain, Saint Lucia (+4 more), Barbados, Trinidad and Tobago, French Guiana, Brazil
Inside
-
Oceanview
-
Balcony
-
Suite
$13,398
From
US$13,398
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Jun 2026 to Oct 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$549
Oceanview
$559
Balcony
$856
Suite
$1,071
From
US$549
Per Person
View Trip
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 31 October 2026
Visit: USA, Bahamas, Turks and Caicos Islands
Exclusive Savings
Inside
$512
Oceanview
$789
Balcony
$959
Suite
$1,585
From
US$733
Save 13
Per Person
View Trip
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Departure: 21 October 2027
Visit: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$664
Oceanview
$804
Balcony
$1,636
Suite
$2,182
From
US$997
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Mar 2027
Visit: USA, Mexico, Belize
Exclusive Savings
Inside
$714
Oceanview
$814
Balcony
$979
Suite
$3,141
From
US$833
Save 641
Per Person
View Trip
New ReleaseCruise

11 Days (10 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Departure: 10 October 2027
Visit: Bahamas, Turks and Caicos Islands, Virgin Islands, Saint Barthelemy, Martinique, Saint Vincent, Barbados
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,048
Suite
$9,995
From
US$8,048
Save 1,947
Per Person
View Trip
Results: 91-120 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