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

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191 Cruises (1,786 Cruise Departures)
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Eurodam
Departures: Oct 2026 to Nov 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Fare Saver
Inside
$649
Oceanview
$699
Balcony
$949
Suite
$1,699
From
US$649
Per Person
View Trip
Cruise

10 Days (9 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 22 October 2027
Visit: USA, Bahamas, Dominican Republic, Haiti, Turks and Caicos Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,092
Oceanview
$1,182
Balcony
$1,694
Suite
$2,329
From
US$1,092
Save 554
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 31 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Honduras, Belize, Mexico
Princess Standard
Sanctuary Collection
Inside
$1,318
Oceanview
$1,468
Balcony
$2,458
Suite
$2,848
From
US$1,318
Per Person
View Trip
Cruise

11 Days (10 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Departure: 22 October 2026
Visit: USA, Turks and Caicos Islands, Saint Martin, Dominica (+4 more), Martinique, Antigua and Barbuda, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
$1,049
Oceanview
-
Balcony
$2,967
Suite
-
From
US$1,049
Save 538
Per Person
View Trip
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2026
Visit: USA, Bahamas, Aruba, Curacao
Exclusive Savings
Inside
$802
Oceanview
$1,266
Balcony
$1,608
Suite
$3,096
From
US$802
Save 636
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 23 October 2027
Visit: USA, Mexico, Honduras, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$734
Oceanview
$824
Balcony
$1,306
Suite
$1,632
From
US$734
Save 404
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
$734
Oceanview
$897
Balcony
$1,052
Suite
$2,086
From
US$734
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Drinks & WiFi Package
Inside
$567
Oceanview
$768
Balcony
$827
Suite
$1,444
From
US$567
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
$619
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$619
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: May 2027 to Dec 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$659
Oceanview
$749
Balcony
$1,192
Suite
$1,496
From
US$659
Save 498
Per Person
View Trip
Cruise

7 Days (6 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$742
Oceanview
$862
Balcony
$922
Suite
$1,692
From
US$742
Save 656
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to Fort Lauderdale
Cruise Line: Royal Caribbean
Departure: 31 October 2027
Visit: USA, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$821
Oceanview
$1,031
Balcony
$1,043
Suite
$2,359
From
US$821
Save 447
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Aug 2027 to Oct 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$997
Oceanview
$1,157
Balcony
$1,187
Suite
$2,550
From
US$997
Save 683
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
$1,058
Oceanview
$1,184
Balcony
$1,726
Suite
-
From
US$1,058
Per Person
View Trip
Cruise

29 Days (28 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 30 October 2027
Visit: USA, Bahamas, Jamaica, Dominican Republic (+12 more), Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Curacao, Aruba, Colombia, Panama, Costa Rica, Belize, Mexico
Book Early & Have It All Fare Option
Inside
$4,179
Oceanview
$4,579
Balcony
$7,079
Suite
$8,859
From
US$4,179
Per Person
View Trip
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 31 October 2026
Visit: USA, Saint Martin, Antigua and Barbuda, Martinique (+4 more), Dominica, Saint Kitts and Nevis, Virgin Islands, Bahamas
Fare Saver
Inside
$949
Oceanview
$1,149
Balcony
$1,299
Suite
$2,799
From
US$949
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$879
Oceanview
$1,009
Balcony
$1,259
Suite
$1,619
From
US$879
Per Person
View Trip
Cruise

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Departure: 29 October 2027
Visit: Puerto Rico, Antigua and Barbuda, Saint Lucia, Grenada, Barbados, Saint Vincent, Virgin Islands
Exclusive Savings
Inside
$879
Oceanview
$916
Balcony
$1,379
Suite
$3,791
From
US$879
Save 520
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
$688
Oceanview
$819
Balcony
$951
Suite
$2,095
From
US$1,029
Save 50
Per Person
View Trip
Cruise

21 Days (20 Nights) Los Angeles to New York
Cruise Line: Norwegian Cruise Line
Departure: 19 October 2027
Visit: USA, Mexico, Guatemala, Costa Rica (+4 more), Panama, Colombia, Jamaica, Bahamas
Inside
$2,419
Oceanview
$3,219
Balcony
$3,969
Suite
$4,569
From
US$2,419
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departure: 30 October 2027
Visit: USA, Bahamas, Dominican Republic, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$1,162
Oceanview
$1,302
Balcony
$1,355
Suite
$2,890
From
US$1,162
Save 588
Per Person
View Trip
New ReleaseCruise

10 Days (9 Nights) Nassau to Miami
Cruise Line: Scenic
Departure: 04 October 2028
Visit: Bahamas, Turks and Caicos Islands, USA
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,540
Suite
$9,213
From
US$6,540
Save 2,255
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2027
Visit: USA, Curacao, Aruba, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,000
Oceanview
$1,199
Balcony
$1,238
Suite
$2,673
From
US$1,000
Save 857
Per Person
View Trip
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,134
Oceanview
$1,149
Balcony
$1,444
Suite
$3,852
From
US$1,342
Save 963
Per Person
View Trip
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 31 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$659
Oceanview
$789
Balcony
$1,264
Suite
$1,649
From
US$659
Per Person
View Trip
Cruise

28 Days (27 Nights) Barcelona to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 October 2026
Visit: Spain, Portugal, Morocco, Antigua and Barbuda, Anguilla, Puerto Rico, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$14,660
From
US$14,660
Per Person
View Trip
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$758
Oceanview
$1,017
Balcony
$1,340
Suite
$2,487
From
US$758
Save 429
Per Person
View Trip
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 20 October 2027
Visit: USA, Curacao, Aruba, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,275
Oceanview
$1,395
Balcony
$2,297
Suite
$2,482
From
US$1,275
Save 644
Per Person
View Trip
New ReleaseCruise

12 Days (11 Nights) Tenerife to Saint John's
Cruise Line: Scenic
Departure: 04 October 2027
Visit: Spain, Saint Martin, Saint Barthelemy, Antigua and Barbuda
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,449
Suite
$8,518
From
US$5,449
Save 2,196
Per Person
View Trip
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Oceania Cruises
Departure: 28 October 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+4 more), Saint Lucia, Grenada, Curacao, Aruba
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,015
Suite
$7,225
From
US$5,015
Save 6,783
Per Person
View Trip
Results: 121-150 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