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Caribbean Cruises Starting In February 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in February 2027, 2028 or 2029? Choose from 451 unique cruises and 2,619 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveller reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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451 Cruises (2,619 Departures)
451 Cruises (2,619 Departures)
Departures
Duration
5 Days
55 Days
Start & End Cities
Ship Size
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Price
$400pp
$203,830pp
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11 Day West Indies Explorer with Viking Cruises
Cruise
 (1)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking
Ships: Viking Sea, Viking Sky
Departures: Nov 2026 to Feb 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia +4 more, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Savings
Balcony
$5,532
Suite
$9,354
From (Per Person)
A$5,532
Save 1,395
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,144
Balcony
$1,834
Suite
$2,294
From (Per Person)
A$1,101
Save 903
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 February 2027
Visits: Puerto Rico, Saint Martin, Martinique, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$973
Oceanview
$1,112
Balcony
$1,627
Suite
$2,775
From (Per Person)
A$973
Per Person
View Trip
12 Day Eastern Caribbean: Windward & Leeward Islands with Holland America
Cruise
 (3)

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Eurodam, Rotterdam
Departures: Mar 2027 to Mar 2028
Visits: USA, Saint Martin, Antigua and Barbuda, Dominica +4 more, Martinique, Saint Kitts and Nevis, Virgin Islands, Bahamas
Fare Saver
Exclusive Savings
Inside
$2,152
Oceanview
$2,389
Balcony
$3,459
Suite
$4,914
From (Per Person)
A$2,152
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Aug 2026 to Mar 2028
Visits: Colombia, Aruba, Curacao, Panama
Exclusive Savings
Inside
$1,460
Oceanview
$1,616
Balcony
$1,930
Suite
$2,254
From (Per Person)
A$1,460
Save 1,525
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departures: Dec 2027 to Mar 2028
Visits: USA, Bahamas, Virgin Islands, Saint Martin, Belize, Honduras, Mexico
Exclusive Savings
Inside
$1,989
Oceanview
-
Balcony
$2,169
Suite
$2,909
From (Per Person)
A$1,989
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$744
Oceanview
$923
Balcony
$1,190
Suite
$2,477
From (Per Person)
A$744
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Jan 2027 to Mar 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$974
Oceanview
$1,172
Balcony
$1,806
Suite
$2,618
From (Per Person)
A$974
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Jan 2028 to Mar 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,160
Oceanview
$1,255
Balcony
$1,600
Suite
$2,777
From (Per Person)
A$1,160
Save 731
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Nov 2026 to Feb 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,692
Oceanview
-
Balcony
$2,201
Suite
$2,939
From (Per Person)
A$1,692
Per Person
View Trip
8 Day Western Caribbean with Grand Cayman with Princess
Cruise
 (3)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Nov 2027 to Feb 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$995
Oceanview
$1,252
Balcony
$1,308
Suite
$1,807
From (Per Person)
A$995
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (3)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 21 February 2027
Visits: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,321
Oceanview
$1,700
Balcony
$1,714
Suite
$1,955
From (Per Person)
A$1,321
Per Person
View Trip
8 Day Western Caribbean with Mexico & Celebration Key with Princess
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departures: Dec 2027 to Mar 2028
Visits: USA, Belize, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$975
Oceanview
-
Balcony
$1,072
Suite
$1,450
From (Per Person)
A$975
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 12 February 2028
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
$1,527
Oceanview
$1,881
Balcony
$2,118
Suite
$5,799
From (Per Person)
A$1,527
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 07 February 2027
Visits: USA, Bahamas, Honduras, Mexico, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$2,102
Oceanview
$2,414
Balcony
$3,572
Suite
$5,394
From (Per Person)
A$2,102
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Dec 2027 to Feb 2028
Visits: USA, Belize, Honduras, Mexico, Bahamas, Virgin Islands, Saint Martin
Sanctuary Collection
Exclusive Savings
Inside
$2,308
Oceanview
$2,643
Balcony
$3,256
Suite
$4,872
From (Per Person)
A$2,308
Per Person
View Trip
22 Day Eastern & Western Caribbean: Leeward Islands & Mexico with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 02 February 2027
Visits: USA, Saint Martin, Antigua and Barbuda, Dominica +9 more, Martinique, Saint Kitts and Nevis, Virgin Islands, Bahamas, Cayman Islands, Jamaica, Honduras, Belize, Mexico
Fare Saver
Exclusive Savings
Inside
$3,690
Oceanview
$4,274
Balcony
$5,809
Suite
$8,363
From (Per Person)
A$3,690
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$825
Oceanview
$946
Balcony
$1,085
Suite
$1,716
From (Per Person)
A$825
Per Person
View Trip
8 Day Southern Caribbean with Puerto Rico with Princess
Cruise
 (12)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ship: Crown Princess
Departure: 26 February 2027
Visits: Barbados, Puerto Rico, Saint Martin, Martinique, Dominica, Grenada
Exclusive Savings
Inside
$1,666
Oceanview
$1,888
Balcony
$2,498
Suite
$2,913
From (Per Person)
A$1,666
Per Person
View Trip
15 Day Southern/Eastern Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 06 February 2027
Visits: USA, Aruba, Curacao, Bonaire, Bahamas, Turks and Caicos Islands
Exclusive Savings
Inside
$4,958
Oceanview
-
Balcony
$7,347
Suite
$8,473
From (Per Person)
A$4,958
Per Person
View Trip
8 Day Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Feb 2027 to Dec 2027
Visits: USA, Cayman Islands, Jamaica, Bahamas
Inside
$1,232
Oceanview
$1,543
Balcony
$1,750
Suite
$4,547
From (Per Person)
A$1,232
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 28 February 2027
Visits: USA, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,093
Oceanview
$1,310
Balcony
$1,786
Suite
$2,281
From (Per Person)
A$1,093
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra
Departures: Dec 2026 to Mar 2027
Visits: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis +4 more, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Exclusive Savings
Oceanview
$6,770
Suite
$7,314
From (Per Person)
A$6,770
Save 4,636
Per Person
View Trip
8 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (12)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visits: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$1,736
Oceanview
$2,013
Balcony
$1,963
Suite
$3,124
From (Per Person)
A$1,736
Per Person
View Trip
11 Day Golden Caribbean Strands with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania
Ship: Oceania Marina
Departure: 23 February 2027
Visits: USA, Puerto Rico, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Dominican Republic, Bahamas
Your World Inclusions
Exclusive Savings
Inside
$2,875
Oceanview
-
Balcony
$4,167
Suite
$5,546
From (Per Person)
A$2,875
Save 3,995
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (12)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 07 February 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +4 more, Dominica, Barbados, Saint Kitts and Nevis, Grenada
Exclusive Savings
Inside
$2,333
Oceanview
$2,635
Balcony
$3,828
Suite
$5,491
From (Per Person)
A$2,333
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 13 February 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,112
Oceanview
$1,680
Balcony
$1,944
Suite
$2,973
From (Per Person)
A$1,112
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos & Celebration Key with Princess
Cruise
 (1)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Nov 2026 to Feb 2027
Visits: USA, Bahamas, Turks and Caicos Islands
Exclusive Savings
Inside
$757
Oceanview
-
Balcony
$836
Suite
$1,321
From (Per Person)
A$757
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 11 February 2028
Visits: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Balcony
$9,330
Suite
$16,562
From (Per Person)
A$9,330
Save 2,570
Per Person
View Trip
12 Day Best Of Southern Caribbean with Celebrity Cruises
Cruise
 (1)

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Ascent
Departures: Dec 2026 to Mar 2027
Visits: USA, Sint Maarten, Antigua and Barbuda, Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis
Exclusive Savings
Inside
$2,026
Oceanview
$2,554
Balcony
$3,353
Suite
$10,430
From (Per Person)
A$2,026
Save 1,698
Per Person
View Trip
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Routes

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Country Routes

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