The first few months of sailings were plagued by poor service, crewmembers quitting and walking off the ship while in port, and an enormous number of customer complaints.

NCL initiated a new and aggressive training program to better prepare newly hired employees for life aboard a cruise vessel.

On June 1, 2012, NCL announced the signing of a memorandum of agreement to exercise its option to purchase Norwegian Sky.

[12][13][14] Hurricane Irma caused cruises to be cancelled; afterwards Norwegian Sky evacuated almost 2,000 travelers from St. Thomas and took them to Miami.

[15][16] In June 2019, it was announced that, following the travel ban preventing U.S. cruise ships from visiting Cuba, Norwegian Sky would no longer be offering their "open bar" service and would instead transition to the traditional way for charging for onboard drinks.

[5] When the ship was refitted for service as Pride of Aloha she received hull art consisting of colorful Hawaiian leis.

The ship introduced a new concept starting in January 2016 and ending in June 2019 where alcohol was included in the cost, with an upcharge only for premium brands.

[19] While doing her inaugural cruise along the Eastern coast of the United States and Canada up to Québec City, Norwegian Sky temporarily ran aground in the Saguenay River on September 24, 1999.

As the vessel was unstable on the reef, the master requested assistance from the Canadian Coast Guard for a preventive evacuation of all passengers plus some crew members.

The Marine Rescue Centre of Québec tasked different resources including whale-watching tour boats and the two provincial ferries normally crossing the Saguenay River.

However, at the very last moment, with the assistance of a small Search and Rescue cutter and the high tide, Norwegian Sky was able to free herself from the reef and proceeded to deeper waters.

[6][20] In May 2001, the autopilot on Norwegian Sky failed and caused it to make a jarring turn and then list, sending plates and glasses crashing and injuring more than 78 people.

[citation needed] After the 100-foot (30.5 m) fish tender Arctic Sun struck a rock and sank in Clarence Strait in the Alexander Archipelago in Southeast Alaska on July 26, 2002, and the three people on board abandoned ship in a 16-foot (4.9 m) skiff, Norwegian Sky rescued them from the skiff and transported them to Ketchikan, Alaska.