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

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191 Cruises (1,786 Cruise Departures)
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Dec 2027
Visit: USA, Bonaire, Aruba, Curacao (+7 more), Dominican Republic, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Inside
$1,931
Oceanview
$2,575
Balcony
$2,701
Suite
-
From
US$1,931
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: May 2027 to Apr 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba (+5 more), Bahamas, Colombia, Panama, Costa Rica, Jamaica
Fare Saver
Inside
$1,879
Oceanview
$2,059
Balcony
$2,779
Suite
$5,619
From
US$1,879
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$879
Balcony
$949
Suite
$1,149
From
US$699
Per Person
View Trip
Cruise
 (1)

21 Days (20 Nights) Marseille to Orlando
Cruise Line: MSC Cruises
Departure: 25 October 2026
Visit: France, Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,124
Oceanview
$1,375
Balcony
$1,642
Suite
-
From
US$1,124
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico
Inside
$389
Oceanview
$509
Balcony
$590
Suite
$1,511
From
US$389
Per Person
View Trip
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire (+7 more), Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Bonus Onboard Credit
Value Fare
Inside
$1,962
Oceanview
$2,152
Balcony
$3,017
Suite
$7,235
From
US$1,962
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 03 October 2026
Visit: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,308
Oceanview
-
Balcony
$1,838
Suite
$2,248
From
US$1,308
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
-
Oceanview
$1,323
Balcony
$1,533
Suite
$4,123
From
US$1,323
Per Person
View Trip
Cruise
 (5)

25 Days (24 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+10 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Azamara Always Included
Inside
$5,949
Oceanview
$7,179
Balcony
$8,859
Suite
$14,029
From
US$5,949
Per Person
View Trip
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,519
Oceanview
$2,169
Balcony
$2,629
Suite
$4,599
From
US$1,519
Per Person
View Trip
Cruise

18 Days (17 Nights) Los Angeles to Tampa
Cruise Line: Celebrity Cruises
Departure: 01 October 2026
Visit: USA, Mexico, Guatemala, Costa Rica (+4 more), Panama, Colombia, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
$1,937
Balcony
$2,844
Suite
-
From
US$1,937
Save 915
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
$1,214
Balcony
$1,709
Suite
$2,449
From
US$854
Per Person
View Trip
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: May 2026 to Sep 2027
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$449
Oceanview
$549
Balcony
$648
Suite
$951
From
US$449
Save 586
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 08 October 2026
Visit: USA, Aruba, Curacao, Dominican Republic, Bahamas
Exclusive Savings
Inside
$902
Oceanview
$1,082
Balcony
$1,274
Suite
$2,380
From
US$1,325
Save 50
Per Person
View Trip
Cruise

17 Days (16 Nights) Montreal to Miami
Cruise Line: Regent Seven Seas
Departure: 30 October 2026
Visit: Canada, Sint Maarten, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,699
Suite
$17,399
From
US$15,699
Save 15,699
Per Person
View Trip
New ReleaseCruise

21 Days (20 Nights) Nassau to Panama City
Cruise Line: Scenic
Departure: 04 October 2028
Visit: Bahamas, Turks and Caicos Islands, USA, Colombia, Panama
Inside
-
Oceanview
-
Balcony
$20,890
Suite
$32,605
From
US$20,890
Per Person
View Trip
Cruise

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: May 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$358
Oceanview
$396
Balcony
$530
Suite
$859
From
US$358
Save 564
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departures: Oct 2026 to May 2027
Visit: USA, Honduras, Belize, Mexico, Bahamas
Inside
$879
Oceanview
$879
Balcony
$1,049
Suite
$1,529
From
US$879
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

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Oct 2027 to Mar 2028
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$654
Oceanview
$774
Balcony
$1,034
Suite
$1,174
From
US$654
Per Person
View Trip
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2027 to Oct 2027
Visit: USA, Curacao, Bonaire, Aruba, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,156
Oceanview
$1,298
Balcony
$2,224
Suite
$2,486
From
US$1,156
Save 618
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
$1,272
Oceanview
$1,603
Balcony
$1,710
Suite
$2,780
From
US$1,272
Save 1,154
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Aug 2026 to Nov 2026
Visit: USA, Virgin Islands, Bahamas
Exclusive Savings
Inside
$805
Oceanview
$1,003
Balcony
$965
Suite
$2,659
From
US$805
Save 496
Per Person
View Trip
Cruise

5 Days (4 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 20 October 2026
Visit: USA, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$514
Oceanview
$704
Balcony
$1,114
Suite
$1,184
From
US$514
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,106
Oceanview
$1,246
Balcony
$1,228
Suite
$3,438
From
US$1,106
Save 563
Per Person
View Trip
Cruise

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Jan 2027
Visit: USA, Curacao, Colombia, Panama, Costa Rica, Bahamas
Princess Standard
Inside
$885
Oceanview
$1,025
Balcony
$1,618
Suite
$2,299
From
US$885
Per Person
View Trip
Cruise

33 Days (32 Nights) Montreal to Los Angeles
Cruise Line: Oceania Cruises
Departure: 10 October 2027
Visit: Canada, Bermuda, Bahamas, USA (+6 more), Cayman Islands, Colombia, Panama, Costa Rica, Guatemala, Mexico
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,399
Suite
$22,049
From
US$15,399
Save 15,399
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: May 2026 to Apr 2028
Visit: USA, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$737
Oceanview
$875
Balcony
$867
Suite
$1,983
From
US$737
Save 1,108
Per Person
View Trip
Cruise

22 Days (21 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 31 October 2026
Visit: USA, Saint Martin, Antigua and Barbuda, Martinique (+8 more), Dominica, Saint Kitts and Nevis, Virgin Islands, Bahamas, Bonaire, Curacao, Aruba, Dominican Republic
Fare Saver
Inside
$1,679
Oceanview
$1,999
Balcony
$2,269
Suite
$4,559
From
US$1,679
Per Person
View Trip
Results: 61-90 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