Caribbean Cruises Starting In October 2026 and 2027

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175 Cruises (1,907 Cruise Departures)
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
$684
Oceanview
$863
Balcony
$1,231
Suite
$3,024
From
US$684
Save 588
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,326
Oceanview
$1,554
Balcony
$1,633
Suite
$2,675
From
US$1,326
Save 1,673
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
Inside
$848
Oceanview
$1,028
Balcony
$1,178
Suite
$2,005
From
US$848
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
$1,125
Oceanview
$1,275
Balcony
$1,315
Suite
$2,815
From
US$1,125
Save 572
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$789
Oceanview
$949
Balcony
$974
Suite
$1,349
From
US$789
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Sep 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$764
Oceanview
$935
Balcony
$1,139
Suite
$1,697
From
US$764
Save 588
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Apr 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$837
Oceanview
$937
Balcony
$967
Suite
$2,036
From
US$978
Save 480
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 25 October 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Saint Martin, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Anguilla
Inside
-
Oceanview
-
Balcony
-
Suite
$8,510
From
US$8,510
Per Person
View Trip
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Dec 2026
Visit: USA, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$525
Oceanview
$675
Balcony
$1,237
Suite
$1,550
From
US$525
Save 673
Per Person
View Trip
Cruise

9 Days (8 Nights) Halifax to Bridgetown
Cruise Line: Seabourn
Departures: Oct 2026 to Oct 2027
Visit: Canada, Saint Kitts and Nevis, Spain, Saint Lucia, Barbados
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,877
From
US$6,877
Save 122
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
$984
Oceanview
$1,184
Balcony
$1,684
Suite
$3,523
From
US$984
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 30 October 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Inside
$1,501
Oceanview
$2,021
Balcony
$2,237
Suite
$3,711
From
US$1,501
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
$1,004
Oceanview
$1,054
Balcony
$1,229
Suite
$3,591
From
US$1,163
Save 367
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
$559
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$559
Per Person
View Trip
Cruise

5 Days (4 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Apr 2026 to Oct 2027
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$344
Oceanview
$369
Balcony
$508
Suite
$808
From
US$344
Save 420
Per Person
View Trip
Cruise

6 Days (5 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Apr 2026 to Sep 2027
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$448
Oceanview
$528
Balcony
$641
Suite
$864
From
US$448
Save 1,007
Per Person
View Trip
Cruise

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Oct 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$387
Oceanview
$429
Balcony
$570
Suite
$921
From
US$387
Save 437
Per Person
View Trip
Cruise

5 Days (4 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departures: Apr 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$420
Oceanview
$475
Balcony
$590
Suite
$926
From
US$420
Save 418
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Oct 2026 to Mar 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$659
Oceanview
$719
Balcony
$939
Suite
$1,029
From
US$659
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
$1,789
Oceanview
$2,079
Balcony
$2,587
Suite
$4,497
From
US$1,789
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$916
Oceanview
$1,067
Balcony
$1,096
Suite
$2,150
From
US$916
Save 3,136
Per Person
View Trip
Cruise
 (3)

17 Days (16 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Departure: 29 October 2026
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$3,905
Oceanview
$4,807
Balcony
$5,612
Suite
$9,220
From
US$3,905
Save 84
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
Exclusive Savings
Inside
$5,711
Oceanview
$6,895
Balcony
$8,524
Suite
$13,549
From
US$5,711
Save 118
Per Person
View Trip
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 31 October 2026
Visit: USA, Bahamas, Mexico
Exclusive Savings
Inside
$840
Oceanview
$891
Balcony
$1,823
Suite
$1,908
From
US$840
Save 476
Per Person
View Trip
Cruise

10 Days (9 Nights) New York to Miami
Cruise Line: Royal Caribbean
Departure: 28 October 2027
Visit: USA, Bermuda, Aruba, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$940
Balcony
$1,320
Suite
$2,360
From
US$840
Save 417
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Mar 2026 to Oct 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$894
Oceanview
$978
Balcony
$1,117
Suite
$2,457
From
US$894
Save 844
Per Person
View Trip
Cruise
 (5)

18 Days (17 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$3,940
Oceanview
$4,619
Balcony
$5,774
Suite
$9,237
From
US$3,940
Save 79
Per Person
View Trip
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 31 October 2026
Visit: USA, Bahamas, Turks and Caicos Islands
Exclusive Savings
Inside
$866
Oceanview
$994
Balcony
$1,235
Suite
$1,558
From
US$866
Save 386
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
$664
Oceanview
$764
Balcony
$839
Suite
$1,139
From
US$664
Per Person
View Trip
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: May 2027 to Oct 2027
Visit: USA, Jamaica, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$770
Oceanview
$819
Balcony
$998
Suite
$1,349
From
US$770
Save 429
Per Person
View Trip
Results: 121-150 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