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Princess Cruises from Orlando

Start your journey from Orlando with 33 unique Princess cruise itineraries to choose from. September is the most popular month to begin your cruise from Orlando and Princess have 78 trips departing this season.
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5 Days
23 Days
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33 Cruises (78 Cruise Departures)
15 Day Southern Caribbean With Martinique & Celebration Key Holiday with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departure: 22 December 2027
Visit: USA, Bahamas, Virgin Islands, Saint Martin (+5 more), Martinique, Saint Lucia, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$1,949
Oceanview
$2,449
Balcony
$3,149
Suite
$4,499
From
US$1,949
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 27 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Princess Standard
Inside
$1,000
Oceanview
$1,150
Balcony
$1,480
Suite
-
From
US$1,000
Per Person
View Trip
7 Day Eastern Caribbean with Celebration Key Holiday with Princess
Cruise
 (2)

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 21 December 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$914
Oceanview
-
Balcony
$1,159
Suite
$1,484
From
US$914
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 29 November 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$691
Oceanview
-
Balcony
$876
Suite
$1,001
From
US$691
Per Person
View Trip
10 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 20 November 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Saint Martin, Bahamas
Princess Standard
Inside
$1,024
Oceanview
-
Balcony
$1,249
Suite
$1,699
From
US$1,024
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos Celebration Key with Princess
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
$514
Oceanview
$649
Balcony
$674
Suite
$954
From
US$514
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$481
Oceanview
$481
Balcony
$706
Suite
$901
From
US$481
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 07 February 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic, Bahamas
Princess Standard
Inside
$704
Oceanview
-
Balcony
$1,089
Suite
$1,224
From
US$704
Per Person
View Trip
6 Day Caribbean Getaway with Celebration Key with Princess
Cruise

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Mar 2028
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$654
Oceanview
$774
Balcony
$874
Suite
$1,174
From
US$654
Per Person
View Trip
7 Day Eastern Caribbean with Turks and Caicos & Celebration Key with Princess
Cruise
 (2)

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 01 March 2027
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Inside
$720
Oceanview
$790
Balcony
$845
Suite
$1,160
From
US$720
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$950
Oceanview
$1,010
Balcony
$2,129
Suite
-
From
US$950
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 21 February 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$723
Oceanview
-
Balcony
$1,048
Suite
$1,153
From
US$723
Per Person
View Trip
17 Day Panama Canal - Ocean To Ocean & Celebration Key with Princess
Cruise

17 Days (16 Nights) Orlando to Los Angeles
Cruise Line: Princess
Ship: Star Princess
Departure: 07 April 2028
Visit: USA, Bahamas, Aruba, Panama, Mexico
Princess Standard
Sanctuary Collection
Inside
$1,950
Oceanview
$2,300
Balcony
$3,600
Suite
$6,600
From
US$1,950
Per Person
View Trip
16 Day Moroccan Passage with Princess
Cruise
 (2)

16 Days (15 Nights) Orlando to London
Cruise Line: Princess
Ship: Sky Princess
Departure: 07 March 2027
Visit: USA, Bermuda, Portugal, Morocco, Spain, England
Princess Standard
Inside
$1,326
Oceanview
-
Balcony
$1,246
Suite
$1,751
From
US$1,246
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star 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
$1,024
Suite
$1,399
From
US$789
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 20 September 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,018
Oceanview
-
Balcony
-
Suite
-
From
US$1,018
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 13 December 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$679
Oceanview
-
Balcony
$824
Suite
$1,029
From
US$679
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$509
Oceanview
$412
Balcony
$754
Suite
$961
From
US$412
Per Person
View Trip
6 Day Caribbean Getaway with Celebration Key Holiday with Princess
Cruise

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departure: 23 November 2027
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$704
Oceanview
$774
Balcony
$874
Suite
$1,174
From
US$704
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos From Orlando with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 11 May 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$777
Oceanview
$832
Balcony
$1,133
Suite
-
From
US$777
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Jan 2027 to Jan 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$674
Oceanview
$779
Balcony
$854
Suite
$1,224
From
US$674
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$946
Oceanview
$999
Balcony
$1,356
Suite
-
From
US$946
Per Person
View Trip
23 Day Moroccan & Iberian Grand Adventure with Princess
Cruise
 (2)

23 Days (22 Nights) Orlando to London
Cruise Line: Princess
Ship: Sky Princess
Departure: 07 March 2027
Visit: USA, Bermuda, Portugal, Morocco, Spain, England, France
Princess Standard
Inside
-
Oceanview
-
Balcony
$2,185
Suite
-
From
US$2,185
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 16 August 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$1,020
Oceanview
$961
Balcony
-
Suite
$2,450
From
US$961
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jun 2026 to Aug 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Princess Standard
Inside
$1,008
Oceanview
$1,098
Balcony
-
Suite
-
From
US$1,008
Per Person
View Trip
5 Day Turks & Caicos Getaway with Princess
Cruise

5 Days (4 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departure: 05 January 2028
Visit: USA, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$574
Oceanview
$774
Balcony
$874
Suite
$1,274
From
US$574
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 27 December 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,421
Oceanview
-
Balcony
$1,586
Suite
$2,001
From
US$1,421
Per Person
View Trip
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$519
Oceanview
$509
Balcony
$744
Suite
$839
From
US$509
Per Person
View Trip
11 Day Southern Caribbean With St. Lucia with Princess
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Dec 2027 to Mar 2028
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Virgin Islands
Princess Standard
Sanctuary Collection
Inside
$774
Oceanview
$1,024
Balcony
$1,249
Suite
$1,499
From
US$774
Per Person
View Trip
10 Day Eastern Caribbean With St. Thomas with Princess
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Nov 2027 to Mar 2028
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Princess Standard
Sanctuary Collection
Inside
$974
Oceanview
$1,254
Balcony
$1,349
Suite
$1,799
From
US$974
Per Person
View Trip
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