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Princess Cruises from Orlando

Start your journey from Orlando with 37 unique Princess cruise itineraries to choose from. August and September are the most popular months to begin your cruise from Orlando and Princess have 83 trips departing this season.
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7 Days
23 Days
Price
$500pp
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37 Cruises (83 Cruise Departures)
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 19 January 2026
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands (+2 more), Saint Martin, Puerto Rico
Summer Swing Sale
INSIDE
$1,309
OCEANVIEW
$1,859
BALCONY
$1,719
SUITE
$2,159
From (per person) 1,309
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 25 January 2026
Countries Visited: USA, Dominican Republic, Saint Martin, Puerto Rico (+2 more), Turks and Caicos Islands, Bahamas
Summer Swing Sale
INSIDE
$1,230
OCEANVIEW
$1,780
BALCONY
$1,661
SUITE
$1,930
From (per person) 1,230
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 25 January 2026
Countries Visited: USA, Dominican Republic, Saint Martin, Puerto Rico (+1 more), Turks and Caicos Islands
Summer Swing Sale
INSIDE
$739
OCEANVIEW
$1,029
BALCONY
$949
SUITE
$1,129
From (per person) 739
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: Sky Princess
Departure: 16 February 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$609
OCEANVIEW
$779
BALCONY
$741
SUITE
$889
From (per person) 609
View Trip
7 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 01 March 2027
Countries Visited: USA, Bahamas, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$609
OCEANVIEW
$812
BALCONY
$668
SUITE
$1,219
From (per person) 609
View Trip
7 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2026 to Feb 2027
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$604
OCEANVIEW
$689
BALCONY
$569
SUITE
$899
From (per person) 569
View Trip
9 Day Eastern Caribbean with St. Thomas with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 30 November 2025
Countries Visited: USA, Turks and Caicos Islands, Puerto Rico, Saint Martin (+1 more), Virgin Islands
Summer Swing Sale
INSIDE
$759
OCEANVIEW
-
BALCONY
$979
SUITE
$1,169
From (per person) 759
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
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$1,269
OCEANVIEW
$1,389
BALCONY
$1,919
SUITE
$2,429
From (per person) 1,269
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
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Summer Swing Sale
INSIDE
$1,279
OCEANVIEW
$1,379
BALCONY
$1,889
SUITE
$2,399
From (per person) 1,279
View Trip
9 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 28 December 2025
Countries Visited: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic (+1 more), Bahamas
Summer Swing Sale
INSIDE
$1,109
OCEANVIEW
$1,449
BALCONY
$1,315
SUITE
$1,699
From (per person) 1,109
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands (+1 more), Puerto Rico
Summer Swing Sale
INSIDE
$1,269
OCEANVIEW
$1,369
BALCONY
$1,879
SUITE
$2,419
From (per person) 1,269
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: May 2026 to Aug 2026
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico (+1 more), Bahamas
Summer Swing Sale
INSIDE
$1,259
OCEANVIEW
$1,369
BALCONY
$1,789
SUITE
$2,469
From (per person) 1,259
View Trip
9 Day Eastern Caribbean with St. Thomas with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 22 February 2026
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico (+1 more), Virgin Islands
Summer Swing Sale
INSIDE
$769
OCEANVIEW
$869
BALCONY
$869
SUITE
$1,079
From (per person) 769
View Trip
9 Day Eastern Caribbean with St. Thomas with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2025 to Feb 2026
Countries Visited: USA, Virgin Islands, Sint Maarten, Puerto Rico (+1 more), Turks and Caicos Islands
Summer Swing Sale
INSIDE
$799
OCEANVIEW
$1,649
BALCONY
$849
SUITE
$1,069
From (per person) 799
View Trip
7 Day Eastern Caribbean with Turks & Caicos From Orlando with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ships: Caribbean Princess, Sky Princess
Departures: Dec 2025 to May 2026
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$569
OCEANVIEW
$629
BALCONY
$679
SUITE
$849
From (per person) 569
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 07 February 2027
Countries Visited: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic (+1 more), Bahamas
Summer Swing Sale
INSIDE
$914
OCEANVIEW
$1,003
BALCONY
$910
SUITE
$1,429
From (per person) 910
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 29 November 2026
Countries Visited: USA, Bahamas, Puerto Rico, Dominican Republic (+1 more), Turks and Caicos Islands
Summer Swing Sale
INSIDE
$714
OCEANVIEW
$818
BALCONY
$769
SUITE
$1,264
From (per person) 714
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
Countries Visited: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$589
OCEANVIEW
$641
BALCONY
$839
SUITE
$1,019
From (per person) 589
View Trip
23 Day Moroccan & Iberian Grand Adventure with Princess
Cruise

23 Days (22 Nights) Orlando to London
Cruise Line: Princess
Ship: Sky Princess
Departure: 08 March 2026
Countries Visited: USA, Portugal, Morocco, Spain (+2 more), England, France
Summer Swing Sale
INSIDE
$1,929
OCEANVIEW
$2,279
BALCONY
$2,299
SUITE
$2,829
From (per person) 1,929
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Summer Swing Sale
INSIDE
$1,279
OCEANVIEW
$1,399
BALCONY
$1,879
SUITE
$2,409
From (per person) 1,279
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
Countries Visited: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands (+1 more), Bahamas
Summer Swing Sale
INSIDE
$1,199
OCEANVIEW
$1,309
BALCONY
$1,789
SUITE
$2,259
From (per person) 1,199
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 13 December 2026
Countries Visited: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands (+1 more), Bahamas
Summer Swing Sale
INSIDE
$694
OCEANVIEW
$939
BALCONY
$851
SUITE
$1,244
From (per person) 694
View Trip
10 Day Eastern Caribbean with St. Thomas with Princess
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 20 November 2026
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico (+2 more), Virgin Islands, Bahamas
Summer Swing Sale
INSIDE
$759
OCEANVIEW
$999
BALCONY
$979
SUITE
$1,629
From (per person) 759
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
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$649
OCEANVIEW
$709
BALCONY
$909
SUITE
$1,169
From (per person) 649
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: Sky Princess
Departure: 05 January 2026
Countries Visited: USA, Turks and Caicos Islands, Bahamas
Summer Swing Sale
INSIDE
$539
OCEANVIEW
$730
BALCONY
$609
SUITE
$809
From (per person) 539
View Trip
7 Day Eastern Caribbean with Turks & Caicos Holiday with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 21 December 2026
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Summer Swing Sale
INSIDE
$869
OCEANVIEW
$1,449
BALCONY
$1,151
SUITE
$1,719
From (per person) 869
View Trip
15 Day Eastern Caribbean Adventurer Holiday with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 22 December 2025
Countries Visited: USA, Bahamas, Dominican Republic, Turks and Caicos Islands (+1 more), Puerto Rico
Summer Swing Sale
INSIDE
$1,939
OCEANVIEW
-
BALCONY
$2,349
SUITE
$3,149
From (per person) 1,939
View Trip
15 Day Eastern Caribbean Adventurer Holiday with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 16 February 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Dominican Republic (+2 more), Puerto Rico, Virgin Islands
Summer Swing Sale
INSIDE
$1,339
OCEANVIEW
-
BALCONY
$1,829
SUITE
$2,029
From (per person) 1,339
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 30 November 2025
Countries Visited: USA, Turks and Caicos Islands, Puerto Rico, Saint Martin (+3 more), Virgin Islands, Bahamas, Dominican Republic
Summer Swing Sale
INSIDE
$1,309
OCEANVIEW
$1,779
BALCONY
$1,659
SUITE
$5,659
From (per person) 1,309
View Trip
16 Day Moroccan Passage with Princess
Cruise

16 Days (15 Nights) Orlando to London
Cruise Line: Princess
Ship: Sky Princess
Departure: 08 March 2026
Countries Visited: USA, Portugal, Morocco, Spain (+1 more), England
Summer Swing Sale
INSIDE
$969
OCEANVIEW
$1,199
BALCONY
$1,028
SUITE
$1,419
From (per person) 969
View Trip
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