Caribbean Cruises Starting In October 2026 and 2027

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5 Days
58 Days
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$130,398pp
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173 Cruises (1,943 Cruise Departures)
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
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,232
Suite
$9,075
From
US$7,232
Save 10,758
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
Bonus Onboard Credit
Inside
$1,257
Oceanview
$1,787
Balcony
$2,545
Suite
$3,961
From
US$1,257
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
Bonus Onboard Credit
Inside
$2,094
Oceanview
$2,324
Balcony
$3,663
Suite
$5,759
From
US$2,094
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
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$12,297
From
US$12,297
Save 221
Per Person
View Trip
New ReleaseCruise
 (1)

13 Days (12 Nights) New York to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 October 2026
Visit: USA, Bermuda, Bahamas, Virgin Islands, Saint Martin, Puerto Rico
Inside
$1,331
Oceanview
$1,548
Balcony
$1,908
Suite
$6,300
From
US$1,331
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
Bonus Onboard Credit
Inside
$2,034
Oceanview
$2,254
Balcony
$2,740
Suite
-
From
US$2,034
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
Bonus Onboard Credit
Inside
$946
Oceanview
$1,066
Balcony
$1,366
Suite
$3,314
From
US$946
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
$1,655
Oceanview
$2,035
Balcony
$3,625
Suite
-
From
US$1,655
Save 787
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
Bonus Onboard Credit
Inside
$1,934
Oceanview
$2,308
Balcony
$2,643
Suite
$11,717
From
US$1,934
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
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,324
Suite
$12,051
From
US$11,324
Save 14,966
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
 (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
Black Friday Sale + Your World Included
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
 (3)

27 Days (26 Nights) Montreal to Bridgetown
Cruise Line: Azamara Cruises
Departure: 19 October 2026
Visit: Canada, USA, Bermuda, Saint Martin (+8 more), Virgin Islands, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$7,464
Oceanview
$7,852
Balcony
$9,598
Suite
$14,933
From
US$7,464
Save 175
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
$21,100
From
US$9,600
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
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,464
Suite
$16,751
From
US$11,464
Save 12,034
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
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,689
Suite
$13,061
From
US$11,689
Save 18,509
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$9,485
Suite
$10,950
From
US$9,485
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Jan 2026 to Apr 2028
Visit: USA, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$698
Oceanview
$808
Balcony
$790
Suite
$1,938
From
US$698
Save 2,687
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$16,615
Suite
$18,740
From
US$16,615
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
$9,495
Suite
$15,995
From
US$9,495
Save 1,500
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
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$14,951
Oceanview
$16,212
Balcony
$24,360
Suite
$32,508
From
US$14,951
Save 15,547
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
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,847
Suite
$21,480
From
US$12,847
Save 13,451
Per Person
View Trip
Results: 151-173 of 173

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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 Cartagena to Cartagena Cruises from Colon to Colon Cruises from Fort Lauderdale to Los Angeles Cruises from Fort Lauderdale to Barcelona Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort Lauderdale to San Diego Cruises from Fort Lauderdale to Vancouver 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 London Cruises from London to Lisbon Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Los Angeles to Vancouver 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 Philadelphia to Philadelphia 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 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 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 Vancouver Cruises from Seattle to Seattle Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Venice to Barcelona Cruises from Venice to Rome

Country Routes

Cruises from Peru to Argentina Cruises from USA to Portugal 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 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 Germany Cruises from Singapore to China 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 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 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 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