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

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100 Cruises (1,568 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
$549
Oceanview
$579
Balcony
$824
Suite
$999
From
US$549
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Nov 2027
Visit: USA, Aruba, Curacao, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$796
Oceanview
$996
Balcony
$1,091
Suite
$2,251
From
US$796
Save 560
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Aug 2027 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$812
Oceanview
$908
Balcony
$932
Suite
$1,960
From
US$812
Save 511
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
$568
Oceanview
$806
Balcony
$996
Suite
$1,678
From
US$568
Save 566
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

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departure: 20 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,098
Oceanview
-
Balcony
-
Suite
-
From
US$1,098
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
$811
Oceanview
$951
Balcony
$1,134
Suite
$3,086
From
US$864
Save 778
Per Person
View Trip
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Sep 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$996
Oceanview
$1,098
Balcony
-
Suite
-
From
US$996
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Sep 2027 to Nov 2027
Visit: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,065
Oceanview
$1,205
Balcony
$1,244
Suite
$2,414
From
US$1,065
Save 555
Per Person
View Trip
New ReleaseCruise

13 Days (12 Nights) New York to Nassau
Cruise Line: Scenic
Departure: 28 September 2027
Visit: USA, Bermuda, Turks and Caicos Islands, Bahamas
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,630
Suite
$13,164
From
US$9,630
Save 1,965
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
$820
Oceanview
$862
Balcony
$1,033
Suite
$2,985
From
US$820
Save 10,270
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Sep 2027 to Dec 2027
Visit: USA, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$836
Oceanview
$947
Balcony
$976
Suite
$1,836
From
US$836
Save 452
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
$521
Oceanview
$541
Balcony
$826
Suite
$1,021
From
US$521
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 25 September 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$685
Oceanview
$765
Balcony
$1,227
Suite
$1,568
From
US$685
Save 387
Per Person
View Trip
Cruise

25 Days (24 Nights) Halifax to Valparaiso
Cruise Line: Seabourn
Departure: 24 September 2028
Visit: Canada, Bermuda, Puerto Rico, Aruba (+4 more), Panama, Ecuador, Peru, Chile
Inside
-
Oceanview
-
Balcony
$13,048
Suite
$17,998
From
US$13,048
Per Person
View Trip
Cruise

5 Days (4 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: May 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$405
Oceanview
$548
Balcony
$641
Suite
$968
From
US$405
Save 434
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
$1,067
Oceanview
$1,175
Balcony
$1,389
Suite
$3,704
From
US$1,067
Save 1,026
Per Person
View Trip
Cruise

16 Days (15 Nights) Reykjavik to Reykjavik
Cruise Line: Silversea
Departure: 08 September 2026
Visit: Iceland, Greenland
Last Minute Fare
All-Inclusive Plus Fare
Inside
-
Oceanview
-
Balcony
$24,900
Suite
$40,100
From
US$24,900
Per Person
View Trip
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departure: 27 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Princess Standard
Inside
$1,110
Oceanview
$1,300
Balcony
$1,730
Suite
-
From
US$1,110
Per Person
View Trip
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
$511
Oceanview
$531
Balcony
$816
Suite
$1,071
From
US$511
Per Person
View Trip
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Sep 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,193
Oceanview
$1,648
Balcony
$1,384
Suite
$2,717
From
US$1,193
Save 674
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: May 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,197
Oceanview
$1,573
Balcony
$1,647
Suite
$2,755
From
US$1,197
Save 1,037
Per Person
View Trip
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Jul 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$1,020
Oceanview
-
Balcony
$2,597
Suite
-
From
US$1,020
Per Person
View Trip
Cruise

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Apr 2027 to Feb 2028
Visit: USA, Bahamas, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$567
Oceanview
$657
Balcony
$699
Suite
$1,080
From
US$567
Save 538
Per Person
View Trip
Cruise

27 Days (26 Nights) Reykjavik to Oranjestad
Cruise Line: Seabourn
Departure: 06 September 2028
Visit: Iceland, Greenland, Canada, Bermuda, Puerto Rico, Aruba
Inside
-
Oceanview
-
Balcony
$21,148
Suite
$31,498
From
US$21,148
Per Person
View Trip
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,024
Oceanview
$1,334
Balcony
$1,172
Suite
$2,985
From
US$1,024
Save 622
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
$735
Oceanview
$937
Balcony
$1,164
Suite
$3,143
From
US$735
Save 727
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,236
Oceanview
$1,554
Balcony
$1,754
Suite
$3,178
From
US$1,236
Save 909
Per Person
View Trip
Cruise

43 Days (42 Nights) Reykjavik to Valparaiso
Cruise Line: Seabourn
Departure: 06 September 2028
Visit: Iceland, Greenland, Canada, Bermuda (+6 more), Puerto Rico, Aruba, Panama, Ecuador, Peru, Chile
Inside
-
Oceanview
-
Balcony
$31,047
Suite
$44,997
From
US$31,047
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Jun 2027 to Nov 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$659
Oceanview
$749
Balcony
$1,199
Suite
$1,471
From
US$659
Save 503
Per Person
View Trip
Results: 61-90 of 100

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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 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 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 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 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 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 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 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