In 1981, Princess began calling at the cruise line's first private Caribbean destination, Palm Island in the Grenadines.

[8][9] Princess Bay was the cruise line's second private island resort, replacing Palm Island, and was marketed as "every castaway's first choice,"[9] primarily featured on the cruise line's Caribbean itineraries from San Juan, Puerto Rico,[10] but is now no longer a Princess private resort.

[11] This greatly enlarged the Princess fleet by eventually adding six ships, making it a major competitor with the other Caribbean cruise lines.

[10] The development was reported to cost $1.2 million and was unveiled in 1992, becoming an exclusive port of call for the cruise line's Western Caribbean itineraries.

[13] In the early 1990s, Princess was operating a fleet of mostly second-hand ships, with the majority having been inherited from the Sitmar Cruises acquisition.

At the same time Princess began transferring some of its older ships to parent company P&O Cruises and their subsidiaries P&O Australia.

[16] In 2001, Princess Cruises headquarters moved from Century City to Santa Clarita, near the Westfield Valencia Town Center.

[26] On April 3, 2008, Micky Arison, the chairman of Carnival Corporation & plc, stated that due to the low value of the United States dollar because of the recession, inflation and high shipbuilding costs, the company would not be ordering any new ships for their U.S.-based brands (Princess, Carnival Cruise Line, and Holland America Line) before the economic situation improved.

[42][43] Sea Princess was acquired by Chinese start-up Sanya International Cruise Development and renamed Charming.

[47] Throughout the pause, Princess staffed all ships with skeleton crew who had been onboard for months longer than anticipated after the hiatus extended beyond original expectations.

In a bid to rebuild consumer confidence, all guests were required to have received a COVID-19 vaccine 14 days prior to departure.

Rules were also enforced regarding the donning of face masks and social distancing, and capacity was reduced during the initial phase of the resumption.

[51][52] After the success of the initial phased rollout of its resumption in the United States and amid the lingering uncertainty surrounding international travel restrictions related to the pandemic, in March 2022, Princess announced it would redeploy several ships from their originally scheduled distant homeports back to those in the United States.

[56] In July 2018, Princess signed a memorandum of agreement with Fincantieri for the construction of two new 175,000 GT ships to be primarily powered by liquefied natural gas (LNG).

[60] Princess Cruises was involved in litigation with General Electric in 1998 over consequential damages and lost profits resulting from a contract the two parties entered into.

Upon noticing surface rust on the turbine rotor, the vessel was brought ashore for cleaning and balancing, but good metal was unintentionally removed.

On appeal, however, the judgement was reversed in favor of General Electric, and Princess Cruises only recovered the price of the contract, less than $232,000.

[83] On August 26, 2013, the crew of Caribbean Princess deliberately discharged 4,227 gallons of oil-contaminated waste off the southern coast of England.

[84] The discharge involved the illegal modification of the vessel's on-board pollution control systems, and was photographed by a newly hired engineer.

[85][86] When the ship subsequently berthed at Southampton, the engineer resigned his position and reported the discharge to the UK Maritime and Coastguard Agency.

"[90] For violation of the probation terms of 2016, Carnival Corporation and Princess were ordered to pay an additional $20 million penalty in 2019.

[93] Shortly before the disease was declared a pandemic, and with over 2700 passengers on board, Ruby Princess sailed into international waters despite a global increase of confirmed cases of COVID-19.

[94] The subsequent discharge of infected passengers into Australia worsened the national pandemic[38] in the country and caused a humanitarian crisis.