With his brother John, he learned the ship building trade and took over the Domain shipyard which later was solely run by John. Alexander became more interested in business and flourished as a merchant trading from his offices and warehouses on the corner of Elizabeth Street and Lords place, the present site of the Hobart Post Office.
Alexander built the largest fleet of sailing ships individually owned south of the Equator, including whalers, barques, schooners and a brigantine. The Hobart-built ships were considered superior in all ways to many of the same type built elsewhere. As the local hardwood was an ideal timber and vessels built from it were extremely hardy, the ‘blue gum’ clippers became famous throughout the world. Alexander sailed his ships under his blue and white McGregor gridiron flag, and one of the original flags is on display today in the Chandelier Lounge Bar.
The brother’s merchant and shipbuilding businesses continued to grow. With the plentiful supply of whales and as the Windjammers were the only link with the rest of the world in the early 1800’s, Hobart Town became the centre of a big ship building and whaling industry.
The site of Lenna was originally owned by Captain James Bayley. He subsequently sold the property to Alexander McGregor who was his partner in the whaling trade and whose daughter, Miss Harriett Bayley, became McGregor’s first wife. The most famous of his ships and his favourite was the ‘Harriett McGregor’.
“Lenna” is the Tasmanian Aboriginal word for “house” or “hut”. Lenna was erected in stages, work on the first section facing McGregor Street (then called Cross Street) was started in 1874 and incorporated the original Bayley house, now the hotel kitchens. The next section was added in 1880. Built of local sandstone and handmade bricks, the Italianate style building is on the Heritage Register and is a historical Hobart landmark mansion.
Behind Lenna and across the park, remains the cottage of the original Battery Point signal station. The lookout on top of Lenna (McGregor’s Lookout) also had a semaphore for signalling ships in the Derwent River. One of Alexander McGregor’s main trade routes was between London and Hobart and when his ship was some 80 days out of London, having sailed via The Horn, he would commence his vigil in this lookout, telescope to eye, watching for her to appear down the channel. Early photographs, prints and paintings of Alexander McGregor’s ships are throughout the hotel. An original oil painting of the barque ‘Harriet McGregor’ painted in 1878 is a feature of the collection.
In 1914, Lenna was purchased by the late Sir Alfred Ashbolt. Many older Hobart residents have happy memories of parties held in the ground floor “drawing room”, now the Chandelier Lounge. The original gas-lit crystal chandelier still hangs in this room. The light was converted to electricity during the Ashbolt’s ownership. The reception room was the “morning room”, and the small room adjacent to the dining room was a study. The eastern end of the dining room was the original dining room, and the western end, a day nursery. On the first floor, the smaller of the function rooms was the main bedroom, and the dressing room off it is now a bar. The seven attic rooms on the second floor were servant’s quarters, housing a cook, housemaid, parlour maid, chauffeur, “useful maid”, a nurse and a gardener.
While Sir Alfred Ashbolt was in London serving as Tasmania’s Agent General, the house was leased and used as a guest house for some years by Mrs Cremmer. From 1942 to 1971, the house was owned by Mr and Mrs A.E (Jack) Boyes and family who had planned to convert it to a hotel, but after Mr Boyes’ death it was divided into three apartments and remained thus until 1971.
In 1971, Innkeepers Limited purchased the property and in 1973, work commenced on the new wing of Lenna. The whole concept has been to blend the charm of old Lenna with the new building, combining all of the comforts of a first class hotel.
The original fountain, which stood in front of the first residence on the site, has been installed in a new setting. A tower at the top of Lenna was used to look out for the safe arrival of Alexander’s ships. Today, guests can take great delight in climbing the stairs to the McGregor Lookout to enjoy the panoramic view of Hobart and feel a sense of history… An absolutely magnificently preserved mansion from a bygone era.