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In the early 1880’s Harley Trott, local merchant and head of the Trott & Cox steamship agency, proposed building a 200-room hotel on Pitts Bay. Because of the financial connection with the Quebec Steamship Company of New York, this proposal was rejected due to land holding regulations. Harley Trott then reduced the scale of the planned hotel to 70 rooms.

With H.R.H. Princess Louise, Duchess of Argyll and daughter of Queen Victoria, spending the winter of 1883 in Bermuda (her husband Lord Lorne was stationed in Ottawa as Governor-General of Canada), Harley Trott also came up with the name of the proposed new hotel – The Princess.

During 1884 the Princess was being built. When it opened on January 1st 1885 it was Bermuda’s first waterfront hotel, built of wood to absorb the local humidity. It was also the first local hotel to offer hot and cold running water and was lighted with gas throughout. A.A. Jones, proprietor of Mansion House in Williamstown, Mass., was manager.
In 1889 and 1895 the Princess was enlarged to double of its original size, adding an enclosed veranda, 400 x 14 feet, with superb views of Hamilton Harbour. Nathan S. Howe had become manager of the hotel and at various times telephones, electricity and elevators were installed for the almost 300 guests that could now be accommodated. In 1897, two years after the enlargements, Harley Trott died, having not quite achieved his dream of a 200-room hotel on Pitts Bay.