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Princess Cruises from Orlando

Start your journey from Orlando with 31 unique Princess cruise itineraries to choose from. September is the most popular month to begin your cruise from Orlando and Princess have 67 trips departing this season.
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23 Days
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31 Cruises (67 Cruise Departures)
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
Princess Premier
Inside
$748
Oceanview
$1,098
Balcony
$1,058
Suite
$1,489
From
US$748
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
Princess Premier
Inside
$934
Oceanview
$1,104
Balcony
$1,089
Suite
$1,504
From
US$934
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
$999
Oceanview
-
Balcony
$1,183
Suite
$1,703
From
US$999
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
$566
Oceanview
$686
Balcony
$686
Suite
$941
From
US$566
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
Princess Premier
Inside
$1,231
Oceanview
$1,421
Balcony
$1,250
Suite
$1,751
From
US$1,231
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
Princess Premier
Inside
$824
Oceanview
$1,014
Balcony
$974
Suite
$1,329
From
US$824
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
Princess Premier
Inside
$549
Oceanview
$709
Balcony
$679
Suite
$854
From
US$549
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
Princess Premier
Inside
$1,581
Oceanview
$1,405
Balcony
$1,686
Suite
$2,031
From
US$1,405
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
Princess Premier
Inside
$2,103
Oceanview
-
Balcony
-
Suite
$9,969
From
US$2,103
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
Princess Plus
Princess Premier
Inside
$499
Oceanview
$669
Balcony
$669
Suite
$814
From
US$499
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
Princess Premier
Inside
$654
Oceanview
$904
Balcony
$874
Suite
$1,049
From
US$654
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
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Princess Premier
Inside
$604
Oceanview
$764
Balcony
$839
Suite
$964
From
US$604
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: Aug 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$1,088
Oceanview
$1,226
Balcony
-
Suite
-
From
US$1,088
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
$799
Oceanview
$999
Balcony
$1,229
Suite
$1,599
From
US$799
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
Departure: 23 August 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Bahamas
Princess Standard
Inside
$1,296
Oceanview
-
Balcony
-
Suite
-
From
US$1,296
Per Person
View Trip
10 Day Eastern Caribbean With St. Thomas & Celebration Key with Princess
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departure: 29 March 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Princess Standard
Sanctuary Collection
Inside
$969
Oceanview
$1,169
Balcony
$1,369
Suite
$1,819
From
US$969
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: Jun 2026 to Oct 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$521
Oceanview
$579
Balcony
$924
Suite
$1,199
From
US$521
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
$824
Balcony
$934
Suite
$1,124
From
US$704
Per Person
View Trip
13 Day Southern Caribbean Islander with Princess
Cruise

13 Days (12 Nights) Orlando to Fort Lauderdale
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 18 October 2026
Visit: USA, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$874
Oceanview
$1,184
Balcony
$1,699
Suite
$2,649
From
US$874
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 Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$579
Oceanview
$599
Balcony
$874
Suite
$1,089
From
US$579
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
$1,410
Oceanview
$1,408
Balcony
-
Suite
-
From
US$1,408
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
$1,230
Oceanview
$1,430
Balcony
$2,511
Suite
-
From
US$1,230
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: 06 September 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$1,210
Oceanview
-
Balcony
-
Suite
-
From
US$1,210
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
$571
Oceanview
$621
Balcony
$956
Suite
$1,331
From
US$571
Per Person
View Trip
17 Day Panama Canal - Ocean to Ocean with Princess
Cruise

17 Days (16 Nights) Orlando to Los Angeles
Cruise Line: Princess
Ship: Star Princess
Departure: 07 April 2028
Visit: USA, Turks and Caicos Islands, Aruba, Panama, Mexico
Princess Standard
Sanctuary Collection
Inside
$1,999
Oceanview
$2,299
Balcony
$2,799
Suite
$3,749
From
US$1,999
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
$899
Oceanview
$1,229
Balcony
$1,369
Suite
$1,749
From
US$899
Per Person
View Trip
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
$1,774
Oceanview
$2,454
Balcony
$3,099
Suite
$4,449
From
US$1,774
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
$644
Oceanview
$794
Balcony
$1,024
Suite
$1,164
From
US$644
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
$564
Oceanview
$764
Balcony
$864
Suite
$1,264
From
US$564
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
$1,368
Oceanview
-
Balcony
-
Suite
-
From
US$1,368
Per Person
View Trip
Results: 1-30 of 31

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