1965

• Company founder Stanley B. McDonald charters Princess Patricia and forms Princess Cruises -- first winter season of Mexico cruises starts in November

1966

• Princess Patricia returned to owners

1967

• Princess Italia chartered (one of first modern ships built specifically for cruising)
• First Panama Canal cruises (company pioneered regularly scheduled Canal cruises)

1968

• Princess Carla chartered
• Seawitch logo makes first appearance
• Boise Cascade purchases Princess
• First Alaska season (Princess Italia)
• First transatlantic sailing (13-day Nassau-Genoa, Princess Italia)

1970

• Stanley McDonald repurchases Princess from Boise Cascade
• Princess Carla returned to owners

1972

• Island Princess joins fleet (formerly Island Venture)
• Princess Tours founded

1973

• Princess Italia returned to owners

1974

• Princess acquired by the Pennisular & Oriental Steam Navigation Company (P&O)
• Pacific Princess joins fleet (formerly Sea Venture)
• Sun Princess joins fleet (formerly P&O's Spirit of London)

1975

• "The Love Boat" TV series developed by producer Aaron Spelling; Princess agrees to become backdrop for the show

1976

• "The Love Boat" begins filming

1979

• Princess Tours acquires Johansen Royal Tours

1980

• Stanley McDonald departs company

1981

• Princess begins calling at first private Caribbean island, Palm Island in Grenadines

1984

• Royal Princess joins fleet (innovative ship features all outside cabins)

1985

• Pacific Princess launches company's first Mediterranean season
• First major cruise line to base a ship in San Diego (Pacific Princess to Mexico)

1986

• Sea Princess joins fleet from P&O (formerly Kungsholm)
• New "Voyage of the Glaciers" route debuts (Vancouver/Whittier on Sea Princess)
• New private island, Mayreau (Grenadines), replaces Palm Island

1987

• Denali Princess Wilderness Lodge opens
• First Caribbean cruises from Miami
• First Asia cruises (Royal Princess)
• First Northern Europe (Baltic) cruises

1988

• Princess acquires Sitmar Cruises
• Dawn Princess joins fleet (formerly Fairwind)
• Fair Princess joins fleet (formerly Fairsea)
• Sky Princess joins fleet (formerly Fairsky)
• Sun Princess sold
• First Midnight Sun Express Railcars built

1989

• Star Princess joins fleet

1990

• Crown Princess joins fleet
• Kenai Princess Wilderness Lodge opens
• Captain's Circle loyalty program begins

1991

• Regal Princess joins fleet
• Sea Princess transferred to P&O as Victoria

1992

• New private island launched (Princess Cays in Eleuthera)

1993

• Golden Princess chartered (formerly Royal Viking Sky)
• Dawn Princess sold
• Fairbanks Princess Hotel opens

1995

• Sun Princess joins fleet (world's largest cruise ship)
• Fair Princess transferred to P&O Australia

1996

• Golden Princess returned to owner
• C.R.U.I.S.E. customer service program debuts

1997

• Dawn Princess joins fleet
• Star Princess transferred to P&O becoming Arcadia
• Mt. McKinley Princess Wilderness Lodge opens

1998

• Grand Princess joins fleet (world's largest cruise ship)
• Sea Princess joins fleet
• "Love Boat: the Next Wave" debuts
• First world cruise (Island Princess -- 64 days Rome/San Francisco)
• Santa Clarita, California customer service center opens
• Princess Cays expanded

1999

• Island Princess sold
• Comprehensive company web site debuts

2000

• P&O Princess demerged from P&O
• Ocean Princess joins fleet
• Sky Princess transferred to P&O Australia becoming Pacific Sky
• First Bermuda cruises (program ran 2000-02)
• Fleet transferred to British/Bermuda registry

2001

• Golden Princess joins fleet
• Princess headquarters moves to Santa Clarita, California
• Use of shore power debuts in Juneau

2002

• Star Princess joins fleet
• Original Pacific Princess sold
• Tahitian Princess joins fleet
• Crown Princess transferred to A'ROSA becoming A'ROSA Blu
• Ocean Princess transferred to P&O becoming Oceana
• Copper River Princess Wilderness Lodge opened

2003

• Princess acquired by Carnival Corporation Coral Princess joins fleet
• New Pacific Princess joins fleet (split deployment with P&O Australia
• New Island Princess joins fleet
• Sea Princess transferred to P&O becoming Adonia
• First Antarctica cruise

2004

• Cunard Line integrated into Princess operations
• Diamond Princess joins fleet
• Caribbean Princess joins fleet
• Sapphire Princess joins fleet
• First Caribbean sailings from Galveston, Texas

2005

• Royal Princess transferred to P&O becoming Artemis
• Sea Princess returns to Princess fleet
• Princess Cruises celebrates 40th anniversary

2006

• Crown Princess joins fleet

2007

• Department of Romance launched
• Emerald Princess joins fleet
• New Royal Princess joins fleet
• Regal Princess transferred to P&O Australia becoming Pacific Dawn

2008

• Ruby Princess joins fleet
• Ultimate Ship Tour debuts

2009 

• Shore power begins in Vancouver
• Tahitian Princess renamed Ocean Princess
• Royal Princess transferred to P&O Cruises to sail as Adonia

2010 

• Digital travel documents debut
• Bon Voyage Experience program begins
• eZAir program debuts
• Shore Power begins in San Francisco

2011 

• Gavin MacLeod 80th birthday party on Golden Princess
• Most significant drydock transformation – Grand Princess
• Princess launches first blog – “50 Essential Experiences”

2012 

• “Inspired to Cruise” blog debuts

2013 

• “Linked by the Sea” blog debuts
• Japan-based cruising begins
• New Royal Princess debuts
• First Cruising with a Cause cruise to support US veterans charities

2014 

• New Regal Princess debuts