Caribbean Cruises Starting In December 2026 and 2027

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37 Days
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499 Cruises (2,642 Cruise Departures)
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,685
Suite
$5,285
From
US$4,685
Per Person
View Trip
Cruise

16 Days (15 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2026
Visit: USA, Mexico, Guatemala, Belize (+6 more), Honduras, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,335
Suite
$7,175
From
US$6,335
Per Person
View Trip
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departure: 31 December 2026
Visit: Barbados, Martinique, Antigua and Barbuda, Virgin Islands, Dominican Republic, Saint Kitts and Nevis, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$2,511
Oceanview
$2,812
Balcony
$3,734
Suite
$4,869
From
US$2,511
Save 67
Per Person
View Trip
Cruise
 (1)

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 10 December 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$3,427
Oceanview
$3,718
Balcony
$5,561
Suite
$7,695
From
US$3,427
Save 3,571
Per Person
View Trip
Cruise

11 Days (10 Nights) Tampa to Tampa
Cruise Line: Regent Seven Seas
Departure: 11 December 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Belize, Mexico
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,707
Suite
$7,859
From
US$6,707
Save 12,141
Per Person
View Trip
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA, Dominican Republic
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$9,600
Suite
$10,835
From
US$9,600
Per Person
View Trip
Cruise
 (2)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 03 December 2026
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Dominica, Antigua and Barbuda
Exclusive Savings
Inside
$1,007
Oceanview
$1,108
Balcony
$1,445
Suite
$4,748
From
US$1,007
Save 725
Per Person
View Trip
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Departure: 19 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Bahamas
Inside
$1,272
Oceanview
$1,512
Balcony
$1,752
Suite
$4,520
From
US$1,272
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,445
From
US$3,850
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Seaview
Departure: 19 December 2026
Visit: Martinique, Guadeloupe, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, Dominica
Bonus Onboard Credit
Inside
$1,378
Oceanview
$1,558
Balcony
$1,808
Suite
$2,216
From
US$1,378
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Eurodam
Departure: 26 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico, Dominican Republic, Turks and Caicos Islands
Fare Saver
Inside
$1,829
Oceanview
$2,119
Balcony
$2,689
Suite
$4,651
From
US$1,829
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Nov 2027 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$748
Oceanview
$807
Balcony
$1,060
Suite
$1,627
From
US$748
Save 491
Per Person
View Trip
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Nov 2026 to Dec 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands
Bonus Onboard Credit
Inside
$848
Oceanview
$1,008
Balcony
$1,198
Suite
$2,334
From
US$848
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Sep 2026 to Apr 2028
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$821
Oceanview
$921
Balcony
$1,196
Suite
$2,943
From
US$821
Save 1,021
Per Person
View Trip
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departures: Nov 2026 to Feb 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Fare Saver
Inside
$644
Oceanview
$744
Balcony
$994
Suite
$1,644
From
US$644
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Apr 2027
Visit: USA, Mexico, Bahamas
Inside
$829
Oceanview
$929
Balcony
$1,099
Suite
$1,219
From
US$829
Per Person
View Trip
Cruise
 (1)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 14 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Saint Martin
Princess Standard
Inside
$1,229
Oceanview
$1,599
Balcony
$1,439
Suite
$2,100
From
US$1,229
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2027 to Jan 2028
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$675
Oceanview
$1,074
Balcony
$929
Suite
$1,450
From
US$675
Per Person
View Trip
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 18 December 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Bonus Onboard Credit
Inside
$2,009
Oceanview
$2,339
Balcony
$2,611
Suite
$4,153
From
US$2,009
Per Person
View Trip
Cruise
 (1)

11 Days (10 Nights) Philadelphia to Philadelphia
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Inside
$1,039
Oceanview
$1,139
Balcony
$1,759
Suite
$1,918
From
US$1,039
Per Person
View Trip
Cruise
 (3)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
$5,114
Oceanview
$5,395
Balcony
$6,666
Suite
$10,546
From
US$5,114
Save 125
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Mar 2026 to Mar 2027
Visit: USA, Honduras, Belize, Mexico
Princess Standard
Princess Premier
Sanctuary Collection
Inside
$484
Oceanview
$774
Balcony
$619
Suite
$799
From
US$484
Per Person
View Trip
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,010
Suite
$6,262
From
US$4,010
Save 89
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,680
Balcony
$4,240
Suite
$8,560
From
US$3,680
Save 920
Per Person
View Trip
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Martinique, Guadeloupe, Antigua and Barbuda, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,010
Balcony
$3,360
Suite
$3,150
From
US$3,010
Save 1,290
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departures: Dec 2026 to Feb 2027
Visit: USA, Bahamas, Aruba, Colombia (+5 more), Panama, Costa Rica, Cayman Islands, Bonaire, Curacao
Fare Saver
Inside
$2,694
Oceanview
$2,974
Balcony
$3,874
Suite
$7,696
From
US$2,694
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Norwegian Cruise Line
Departures: Oct 2026 to Apr 2028
Visit: USA, Mexico, Honduras, Belize
Exclusive Savings
Inside
$789
Oceanview
$989
Balcony
$1,109
Suite
$1,279
From
US$789
Save 53
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Departures: Dec 2027 to Apr 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin
Princess Standard
Inside
$825
Oceanview
-
Balcony
$1,249
Suite
$1,950
From
US$825
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departure: 16 December 2027
Visit: USA, Haiti, Dominican Republic, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$843
Oceanview
$906
Balcony
$1,176
Suite
$1,407
From
US$843
Save 439
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Dec 2026 to Feb 2027
Visit: USA, Honduras, Belize, Mexico, Turks and Caicos Islands, Dominican Republic, Bahamas
Princess Standard
Sanctuary Collection
Inside
$1,376
Oceanview
$1,738
Balcony
$1,898
Suite
$2,526
From
US$1,376
Per Person
View Trip
Results: 211-240 of 499

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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