Caribbean Cruises Starting In December 2026 and 2027

Filter Results
Departures
Duration
5 Days
37 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$100pp
$135,698pp
Countries
Show More...
Filter Results
526 Cruises (2,663 Cruise Departures)
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Jan 2027 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$493
Oceanview
$583
Balcony
$1,088
Suite
$1,426
From
US$493
Save 579
Per Person
View Trip
Cruise
 (3)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Departures: Nov 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$1,609
Oceanview
$1,969
Balcony
$2,507
Suite
$3,942
From
US$1,609
Per Person
View Trip
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 17 December 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin
Bonus Onboard Credit
Inside
$1,349
Oceanview
$1,549
Balcony
$1,869
Suite
$3,829
From
US$1,349
Per Person
View Trip
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 17 December 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+6 more), Barbados, Saint Martin, Cayman Islands, Jamaica, Honduras, Mexico
Bonus Onboard Credit
Inside
$2,367
Oceanview
$2,443
Balcony
$3,308
Suite
$8,306
From
US$2,367
Per Person
View Trip
Cruise

10 Days (9 Nights) Jacksonville to Jacksonville
Cruise Line: Norwegian Cruise Line
Departure: 09 December 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Dominican Republic
Inside
$1,069
Oceanview
$1,269
Balcony
$1,839
Suite
$2,131
From
US$1,069
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
 (3)

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 20 December 2027
Visit: USA, Mexico, Belize, Honduras (+6 more), Bahamas, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Dominican Republic
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
$4,849
Oceanview
$6,498
Balcony
$7,905
Suite
$10,669
From
US$4,849
Save 5,049
Per Person
View Trip
Cruise
 (2)

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2026 to Feb 2027
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$504
Oceanview
$709
Balcony
$669
Suite
$904
From
US$504
Per Person
View Trip
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Departure: 21 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,046
Oceanview
$1,215
Balcony
$1,648
Suite
$2,212
From
US$1,046
Save 571
Per Person
View Trip
Cruise
 (3)

9 Days (8 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Departure: 28 December 2026
Visit: Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,586
Oceanview
$3,187
Balcony
$4,022
Suite
$6,505
From
US$2,586
Save 63
Per Person
View Trip
Cruise
 (3)

20 Days (19 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departure: 20 December 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Dominican Republic (+5 more), Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Inside
$2,719
Oceanview
$3,059
Balcony
$3,956
Suite
$7,347
From
US$2,719
Per Person
View Trip
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,189
Oceanview
$2,684
Balcony
$3,266
Suite
$4,973
From
US$2,189
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,042
Oceanview
$1,232
Balcony
$1,532
Suite
$2,780
From
US$1,042
Save 58
Per Person
View Trip
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 December 2026
Visit: Puerto Rico, Antigua and Barbuda, Guadeloupe, Virgin Islands, Dominican Republic, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$6,840
From
US$6,840
Per Person
View Trip
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$589
Oceanview
$629
Balcony
$859
Suite
$999
From
US$589
Per Person
View Trip
Cruise

16 Days (15 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 27 December 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis (+4 more), Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat
Inside
-
Oceanview
-
Balcony
-
Suite
$8,505
From
US$8,505
Per Person
View Trip
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Departure: 28 December 2027
Visit: USA, Mexico, Belize
Bonus Onboard Credit
Exclusive Savings
Inside
$1,261
Oceanview
$1,381
Balcony
$1,561
Suite
$2,386
From
US$1,261
Save 636
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
$726
Oceanview
$786
Balcony
$1,018
Suite
$1,638
From
US$726
Save 481
Per Person
View Trip
Cruise

8 Days (7 Nights) Marigot to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe
Inside
-
Oceanview
$8,220
Balcony
$11,650
Suite
$12,530
From
US$8,220
Per Person
View Trip
Cruise
 (1)

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departure: 30 December 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$1,508
Oceanview
$1,658
Balcony
$1,898
Suite
$2,975
From
US$1,508
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 Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,920
Suite
$3,710
From
US$3,710
Save 1,590
Per Person
View Trip
Cruise
 (1)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 20 December 2026
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Inside
$699
Oceanview
-
Balcony
$817
Suite
$1,199
From
US$699
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 05 December 2026
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Dominican Republic, Turks and Caicos Islands, Bahamas
Inside
$1,116
Oceanview
$1,406
Balcony
$1,696
Suite
$6,362
From
US$1,116
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$2,063
Oceanview
$2,324
Balcony
$2,998
Suite
$3,666
From
US$2,063
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Seaside
Departure: 28 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$1,298
Oceanview
-
Balcony
$1,678
Suite
$2,043
From
US$1,298
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Departures: Nov 2027 to Dec 2027
Visit: Puerto Rico, Aruba, Barbados, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,419
Oceanview
$1,619
Balcony
$1,817
Suite
$2,690
From
US$1,419
Save 52
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Mar 2027
Visit: USA, Saint Martin, Virgin Islands, Dominican Republic
Bonus Onboard Credit
Exclusive Savings
Inside
$837
Oceanview
$926
Balcony
$1,084
Suite
$2,070
From
US$837
Save 622
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin
Exclusive Savings
Inside
$1,101
Oceanview
$1,151
Balcony
$1,576
Suite
$3,760
From
US$1,301
Save 450
Per Person
View Trip
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departure: 20 December 2026
Visit: USA, Mexico, Belize, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,164
Oceanview
$1,174
Balcony
$1,465
Suite
$2,941
From
US$1,164
Save 621
Per Person
View Trip
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Dec 2027 to Apr 2028
Visit: USA, Dominican Republic, Haiti, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$775
Oceanview
$865
Balcony
$1,015
Suite
$1,495
From
US$775
Save 525
Per Person
View Trip
Results: 211-240 of 526

No trips found. Try adjusting 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 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