Caribbean Cruises Starting In May 2026 and 2027

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90 Cruises (1,666 Cruise Departures)
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: May 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$491
Oceanview
$509
Balcony
$776
Suite
$911
From
US$491
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 02 May 2027
Visit: USA, Virgin Islands, Dominican Republic, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$1,343
Oceanview
$1,603
Balcony
$1,666
Suite
$2,896
From
US$1,343
Save 683
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Apr 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Inside
$459
Oceanview
$749
Balcony
$619
Suite
$909
From
US$459
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
$970
Balcony
$1,263
Suite
$1,298
From
US$866
Save 1,106
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: MSC Cruises
Ship: MSC Seascape
Departures: Mar 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Inside
$309
Oceanview
$429
Balcony
$499
Suite
$1,275
From
US$309
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: May 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$809
Oceanview
$974
Balcony
$1,194
Suite
$2,970
From
US$809
Save 2,764
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departure: 17 May 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
-
Oceanview
$1,095
Balcony
$1,468
Suite
$3,900
From
US$1,095
Save 609
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 03 May 2026
Visit: USA, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,267
Oceanview
$1,429
Balcony
$1,512
Suite
$2,371
From
US$1,267
Save 32
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departure: 19 May 2026
Visit: USA, Bahamas, Mexico
Inside
$479
Oceanview
$609
Balcony
$659
Suite
$679
From
US$479
Per Person
View Trip
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: May 2027 to Oct 2027
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,095
Oceanview
$1,215
Balcony
$1,415
Suite
$3,463
From
US$1,095
Save 954
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
$3,010
From
US$797
Save 665
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Departures: May 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$823
Oceanview
$843
Balcony
$1,056
Suite
$1,166
From
US$823
Save 908
Per Person
View Trip
Cruise

5 Days (4 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: May 2026 to Dec 2026
Visit: USA, Turks and Caicos Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$578
Oceanview
$729
Balcony
$863
Suite
$1,022
From
US$578
Save 501
Per Person
View Trip
Cruise

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$838
Oceanview
$1,048
Balcony
$1,188
Suite
$2,093
From
US$838
Per Person
View Trip
Cruise

12 Days (11 Nights) Baltimore to Baltimore
Cruise Line: Royal Caribbean
Departure: 10 May 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,191
Oceanview
$1,431
Balcony
$2,651
Suite
$2,985
From
US$1,725
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,440
Oceanview
$1,560
Balcony
$1,680
Suite
$3,130
From
US$1,440
Save 1,028
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
$1,473
From
US$689
Save 568
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2027 to Jul 2027
Visit: USA, Bahamas, Jamaica, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$818
Oceanview
$968
Balcony
$1,085
Suite
$2,186
From
US$818
Save 665
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: May 2026 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$604
Oceanview
$723
Balcony
$904
Suite
$1,754
From
US$604
Save 922
Per Person
View Trip
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Jul 2026 to Jul 2027
Visit: USA, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,147
Oceanview
$1,297
Balcony
$1,297
Suite
$2,298
From
US$1,147
Save 784
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, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,042
Oceanview
$1,232
Balcony
$1,532
Suite
$2,780
From
US$1,042
Save 58
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departure: 02 May 2026
Visit: USA, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,144
Oceanview
$1,641
Balcony
$1,672
Suite
$4,351
From
US$1,699
Save 50
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: Apr 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$1,265
Oceanview
$1,791
Balcony
$2,081
Suite
$3,498
From
US$1,265
Save 66
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Royal Caribbean
Departure: 01 May 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin, Turks and Caicos Islands, USA
Exclusive Savings
Inside
$1,034
Oceanview
-
Balcony
-
Suite
-
From
US$1,542
Save 50
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$374
Oceanview
$408
Balcony
$438
Suite
$848
From
US$374
Save 674
Per Person
View Trip
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 01 May 2026
Visit: USA, Virgin Islands, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$949
Oceanview
$1,150
Balcony
$1,682
Suite
$2,771
From
US$949
Save 80
Per Person
View Trip
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Sep 2026
Visit: USA, Jamaica, Cayman Islands, Bahamas
Exclusive Savings
Inside
$651
Oceanview
$821
Balcony
$997
Suite
$1,448
From
US$651
Save 437
Per Person
View Trip
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Nov 2026 to Nov 2027
Visit: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Inside
$559
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$559
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
$768
Oceanview
$865
Balcony
$965
Suite
$2,502
From
US$898
Save 715
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
Results: 31-60 of 90

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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 Rio de Janeiro 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 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 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