Caribbean Cruises Starting In October 2026 and 2027

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58 Days
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$135,698pp
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175 Cruises (1,907 Cruise Departures)
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Barbados, Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin, Antigua and Barbuda
Drinks & WiFi Package
Exclusive Savings
Inside
$1,428
Oceanview
$1,748
Balcony
$2,667
Suite
$3,792
From
US$1,428
Save 72
Per Person
View Trip
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Dec 2027
Visit: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Inside
$939
Oceanview
$1,039
Balcony
$1,289
Suite
$3,412
From
US$939
Per Person
View Trip
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Aug 2027
Visit: USA, Cayman Islands, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,055
Oceanview
$1,155
Balcony
$1,330
Suite
$4,189
From
US$1,055
Save 554
Per Person
View Trip
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 30 October 2027
Visit: USA, Turks and Caicos Islands, Curacao, Aruba, Bonaire
Exclusive Savings
Inside
$1,154
Oceanview
$1,279
Balcony
$1,321
Suite
$4,543
From
US$1,365
Save 471
Per Person
View Trip
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$763
Oceanview
$865
Balcony
$965
Suite
$2,502
From
US$892
Save 493
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$739
Oceanview
$709
Balcony
$1,169
Suite
$1,379
From
US$709
Save 456
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Departures: Nov 2026 to Apr 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Limited Time Offer
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,550
From
US$595
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$759
Oceanview
$999
Balcony
$1,049
Suite
$1,319
From
US$759
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$991
Oceanview
$989
Balcony
$1,104
Suite
$3,515
From
US$1,177
Save 523
Per Person
View Trip
Cruise

13 Days (12 Nights) Orlando to Fort Lauderdale
Cruise Line: Princess
Departure: 18 October 2026
Visit: USA, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$854
Oceanview
$924
Balcony
$1,329
Suite
$1,949
From
US$854
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 Nov 2027
Visit: Martinique, Antigua and Barbuda, Dominican Republic, Barbados
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 31 October 2027
Visit: USA, Dominican Republic, Bahamas
Exclusive Savings
Inside
$797
Oceanview
$897
Balcony
$997
Suite
$2,297
From
US$937
Save 330
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$797
Oceanview
$852
Balcony
$1,024
Suite
$3,007
From
US$935
Save 471
Per Person
View Trip
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 24 October 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$593
Oceanview
$733
Balcony
$896
Suite
$1,151
From
US$593
Save 386
Per Person
View Trip
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Bonus Onboard Credit
Inside
$969
Oceanview
$1,099
Balcony
$1,339
Suite
$2,869
From
US$969
Per Person
View Trip
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$619
Oceanview
-
Balcony
$874
Suite
$1,069
From
US$619
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Apr 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,525
Oceanview
$1,640
Balcony
$1,716
Suite
$3,316
From
US$1,525
Save 904
Per Person
View Trip
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$584
Oceanview
$744
Balcony
$769
Suite
$1,239
From
US$584
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,208
Oceanview
$1,587
Balcony
$1,521
Suite
$2,984
From
US$1,208
Save 697
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Norwegian Cruise Line
Departures: Oct 2026 to Apr 2028
Visit: USA, Mexico, Honduras, Belize
Inside
$759
Oceanview
$959
Balcony
$1,059
Suite
$1,209
From
US$759
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Dominican Republic
Inside
$986
Oceanview
$1,282
Balcony
$1,552
Suite
$2,828
From
US$986
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Departures: Oct 2026 to Nov 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$739
Oceanview
$810
Balcony
$1,003
Suite
$3,196
From
US$872
Save 608
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Departures: May 2026 to Mar 2028
Visit: Colombia, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$866
Oceanview
$913
Balcony
$1,107
Suite
$1,178
From
US$866
Save 1,106
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,448
From
US$689
Save 568
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 10 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$539
Oceanview
-
Balcony
$574
Suite
$849
From
US$539
Per Person
View Trip
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$524
Oceanview
$583
Balcony
$655
Suite
$1,281
From
US$524
Save 471
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 31 October 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands (+9 more), Honduras, Belize, Mexico, Saint Martin, Antigua and Barbuda, Dominica, Saint Lucia, Saint Kitts and Nevis, Virgin Islands
Fare Saver
Inside
$1,924
Oceanview
$2,304
Balcony
$3,164
Suite
$4,563
From
US$1,924
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Sep 2026 to Apr 2028
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$869
Oceanview
$996
Balcony
$1,175
Suite
$2,958
From
US$1,036
Save 582
Per Person
View Trip
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Departures: Apr 2026 to Nov 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Bonus Onboard Credit
Inside
$1,189
Oceanview
$1,399
Balcony
$1,729
Suite
$3,569
From
US$1,189
Per Person
View Trip
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 25 October 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Limited Time Offer
Inside
-
Oceanview
$1,314
Balcony
$1,374
Suite
$2,814
From
US$1,314
Per Person
View Trip
Results: 61-90 of 175

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Routes

Cruises from Baltimore to Baltimore 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 Los Angeles Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Barcelona 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 Fort Lauderdale Cruises from London to Reykjavik 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 Barcelona Cruises from Rome to Lisbon 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 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 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 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 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 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 USA to Panama Cruises from USA to Peru Cruises from USA to Spain