Caribbean Cruises Starting In October 2026 and 2027

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58 Days
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175 Cruises (1,907 Cruise Departures)
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,557
Oceanview
$1,763
Balcony
$1,832
Suite
$2,695
From
US$1,557
Save 990
Per Person
View Trip
Cruise
 (1)

18 Days (17 Nights) Barcelona to Galveston
Cruise Line: Norwegian Cruise Line
Departure: 14 October 2026
Visit: Spain, Portugal, Saint Martin, Dominican Republic, Jamaica, USA
Inside
$1,949
Oceanview
$2,144
Balcony
$2,270
Suite
$4,064
From
US$1,949
Per Person
View Trip
Cruise
 (13)

28 Days (27 Nights) Barcelona to Miami
Cruise Line: Cunard
Departure: 29 October 2027
Visit: Spain, USA, Virgin Islands, Saint Kitts and Nevis (+4 more), Grenada, Barbados, Saint Lucia, Saint Martin
Inside
$4,139
Oceanview
$4,939
Balcony
$5,989
Suite
$14,850
From
US$4,139
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
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,761
Suite
$9,738
From
US$6,761
Save 884
Per Person
View Trip
Cruise

19 Days (18 Nights) Rome to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 29 October 2026
Visit: Italy, France, Spain, Morocco (+4 more), Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominican Republic
Inside
$1,146
Oceanview
$1,630
Balcony
$2,451
Suite
$3,961
From
US$1,146
Per Person
View Trip
Cruise

26 Days (25 Nights) Rome to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 29 October 2026
Visit: Italy, France, Spain, Morocco (+8 more), Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Inside
$2,236
Oceanview
$2,505
Balcony
$3,845
Suite
$5,917
From
US$2,236
Per Person
View Trip
Cruise

25 Days (24 Nights) Halifax to Rio de Janeiro
Cruise Line: Seabourn
Departures: Oct 2026 to Oct 2027
Visit: Canada, Saint Kitts and Nevis, Spain, Saint Lucia (+4 more), Barbados, Trinidad and Tobago, French Guiana, Brazil
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$15,340
From
US$15,340
Save 277
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departure: 31 October 2027
Visit: USA, Jamaica, Colombia, Panama (+7 more), Costa Rica, Honduras, Belize, Bonaire, Aruba, Dominican Republic, Cayman Islands
Inside
$2,029
Oceanview
$2,249
Balcony
$2,735
Suite
-
From
US$2,029
Per Person
View Trip
Cruise
 (1)

13 Days (12 Nights) Fort-de-France to Colon
Cruise Line: Ponant
Ship: Le Bellot
Departure: 26 October 2026
Visit: Martinique, Guadeloupe, Saint Lucia, Saint Vincent, Bonaire, Colombia, Panama
Inside
-
Oceanview
-
Balcony
$7,550
Suite
$11,910
From
US$7,550
Per Person
View Trip
New ReleaseCruise

12 Days (11 Nights) Bridgetown to Panama City
Cruise Line: Scenic
Departure: 20 October 2027
Visit: Barbados, Saint Lucia, Saint Vincent, Curacao, Colombia, Panama
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,075
Suite
$13,235
From
US$11,075
Save 1,355
Per Person
View Trip
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
$1,929
Oceanview
$2,347
Balcony
$2,638
Suite
$12,008
From
US$1,929
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
Exclusive Savings
Inside
$2,368
Oceanview
$3,144
Balcony
$3,872
Suite
$4,454
From
US$2,368
Save 51
Per Person
View Trip
Cruise
 (3)

12 Days (11 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Nov 2026 to Mar 2028
Visit: USA, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Exclusive Savings
Inside
$943
Oceanview
$1,063
Balcony
$1,363
Suite
$3,767
From
US$943
Save 54
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
Exclusive Savings
Inside
$3,806
Oceanview
$4,296
Balcony
$6,746
Suite
$8,706
From
US$3,806
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
$1,508
Oceanview
$2,502
Balcony
$3,850
Suite
$14,926
From
US$1,711
Save 455
Per Person
View Trip
Cruise

26 Days (25 Nights) Montreal to Miami
Cruise Line: Silversea
Departure: 24 October 2026
Visit: Canada, USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Montserrat
All-Inclusive Fare
Inside
-
Oceanview
$9,600
Balcony
$11,800
Suite
$24,800
From
US$9,600
Per Person
View Trip
Cruise
 (1)

28 Days (27 Nights) Montreal to Miami
Cruise Line: Oceania Cruises
Departure: 25 October 2027
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Bonaire, Curacao, Aruba, Jamaica, Cayman Islands
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$8,568
Oceanview
$9,392
Balcony
$13,369
Suite
$18,607
From
US$8,568
Save 8,930
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
$14,825
Suite
$16,001
From
US$14,825
Save 15,373
Per Person
View Trip
Cruise

26 Days (25 Nights) Montreal to Miami
Cruise Line: Oceania Cruises
Departure: 17 October 2026
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda (+5 more), Saint Kitts and Nevis, Saint Lucia, Grenada, Curacao, Aruba
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,949
Suite
$17,042
From
US$11,949
Save 12,549
Per Person
View Trip
Cruise

18 Days (17 Nights) Quebec City to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 October 2026
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$8,855
From
US$8,855
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Apr 2028
Visit: USA, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$650
Oceanview
$739
Balcony
$781
Suite
$1,948
From
US$650
Save 1,108
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
Inside
-
Oceanview
-
Balcony
-
Suite
$15,375
From
US$15,375
Per Person
View Trip
Cruise
 (1)

20 Days (19 Nights) New York to Santiago
Cruise Line: Viking Cruises
Departure: 25 October 2026
Visit: USA, Bahamas, Jamaica, Panama, Peru, Chile
Flights Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,995
Suite
$14,995
From
US$8,995
Save 2,000
Per Person
View Trip
Cruise
 (1)

58 Days (57 Nights) Venice to Miami
Cruise Line: Oceania Cruises
Departure: 23 October 2026
Visit: Italy, Croatia, Montenegro, Greece (+14 more), Sicily, Spain, Portugal, Puerto Rico, Bahamas, USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Brazil, Barbados, Dominica, Saint Martin
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
$16,309
Balcony
$24,603
Suite
$33,090
From
US$16,309
Save 16,989
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 Inclusions
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,944
Suite
$21,480
From
US$12,944
Save 13,554
Per Person
View Trip
Results: 151-175 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