Caribbean Cruises Starting In October 2026 and 2027

Filter Results
Departures
Duration
5 Days
58 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$100pp
$130,398pp
Countries
Show More...
Filter Results
173 Cruises (1,943 Cruise Departures)
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
$486
Oceanview
$536
Balcony
$691
Suite
$811
From
US$486
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
$1,070
Oceanview
$1,170
Balcony
$1,370
Suite
$3,452
From
US$1,070
Save 1,177
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
Bonus Onboard Credit
Inside
$828
Oceanview
$1,018
Balcony
$1,168
Suite
$2,044
From
US$828
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Nov 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Honduras, Belize, Mexico
Princess Standard
Sanctuary Collection
Inside
$1,518
Oceanview
$1,758
Balcony
$2,068
Suite
$2,808
From
US$1,518
Per Person
View Trip
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$514
Oceanview
$609
Balcony
$634
Suite
$1,281
From
US$514
Save 465
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
$1,040
Oceanview
$1,140
Balcony
$1,340
Suite
$3,452
From
US$1,040
Save 934
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$709
Oceanview
$1,049
Balcony
$1,149
Suite
$1,359
From
US$709
Per Person
View Trip
Cruise

11 Days (10 Nights) Boston to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 20 October 2026
Visit: USA, Curacao, Bonaire, Aruba
Exclusive Savings
Inside
$1,322
Oceanview
-
Balcony
$1,531
Suite
$8,652
From
US$1,322
Save 797
Per Person
View Trip
Cruise

7 Days (6 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Nov 2026
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$562
Oceanview
$642
Balcony
$765
Suite
$1,235
From
US$562
Save 384
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,376
Oceanview
$1,496
Balcony
$1,606
Suite
$3,029
From
US$1,376
Save 1,016
Per Person
View Trip
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Bonus Onboard Credit
Inside
$808
Oceanview
$988
Balcony
$1,128
Suite
$1,908
From
US$808
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 07 October 2027
Visit: USA, Bahamas, Dominican Republic, Curacao, Bonaire, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$1,031
Oceanview
$1,185
Balcony
$1,770
Suite
$1,924
From
US$1,031
Save 508
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$509
Oceanview
$649
Balcony
$659
Suite
$1,319
From
US$509
Per Person
View Trip
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
$644
Oceanview
$744
Balcony
$994
Suite
$1,944
From
US$644
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
Upgrade Your Experience
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,884
Suite
$8,037
From
US$4,884
Save 5,114
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
$1,049
Oceanview
$1,109
Balcony
$1,499
Suite
$2,399
From
US$1,049
Per Person
View Trip
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$929
Oceanview
$979
Balcony
$1,154
Suite
$3,492
From
US$929
Save 601
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departures: Jan 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$688
Oceanview
$947
Balcony
$958
Suite
$1,368
From
US$688
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: MSC Cruises
Ship: MSC Seascape
Departures: Jan 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$399
Oceanview
$489
Balcony
$519
Suite
$1,169
From
US$399
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Oct 2026 to Nov 2026
Visit: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$1,448
Oceanview
$1,628
Balcony
$1,958
Suite
$2,728
From
US$1,448
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$504
Oceanview
$536
Balcony
$699
Suite
$899
From
US$504
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
$877
Oceanview
$1,081
Balcony
$1,296
Suite
$2,240
From
US$877
Save 604
Per Person
View Trip
New ReleaseCruise

11 Days (10 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Departure: 10 October 2027
Visit: Bahamas, Turks and Caicos Islands, Virgin Islands, Saint Barthelemy, Martinique, Saint Vincent, Barbados
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,018
Suite
$9,746
From
US$9,018
Save 12,672
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
$813
Oceanview
$834
Balcony
$1,141
Suite
$2,808
From
US$813
Save 763
Per Person
View Trip
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 30 October 2027
Visit: USA, Turks and Caicos Islands, Curacao, Aruba, Bonaire
Exclusive Savings
Inside
$1,104
Oceanview
$1,204
Balcony
$1,304
Suite
$3,447
From
US$1,104
Save 773
Per Person
View Trip
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Barbados, Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin, Antigua and Barbuda
Bonus Onboard Credit
Exclusive Savings
Inside
$1,288
Oceanview
$1,578
Balcony
$2,337
Suite
$3,578
From
US$1,288
Save 50
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Feb 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Bonus Onboard Credit
Inside
$399
Oceanview
$489
Balcony
$619
Suite
$1,377
From
US$399
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Feb 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$779
Oceanview
$929
Balcony
$1,129
Suite
$1,849
From
US$779
Save 55
Per Person
View Trip
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 30 October 2026
Visit: USA, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$630
Oceanview
$730
Balcony
$722
Suite
$1,032
From
US$630
Save 370
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
$690
Oceanview
$780
Balcony
$1,232
Suite
$1,473
From
US$690
Save 503
Per Person
View Trip
Results: 91-120 of 173

No results found. Try amending the search filters.

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