Horse and buggy, cart, sleigh, train, and boat were the most common conveyances when Montgomery was growing up. The mainland could be reached from Prince Edward Island by boat only when the water was free enough from ice. She did not have her first train ride until she was fifteen (see Out West) even though the nearest train station was only 13 miles / 20 kilometers away in Hunter River.

The success of her novels brought Montgomery a new world of travel. While she had crossed Canada by train with her grandfather when she was fifteen, and had made trips to Halifax for school and work, her first adult traveling adventure was to Boston to meet her publisher in 1910 when she was thirty-five years old. When she married the Rev. Ewan Macdonald a year later, she was able to pay for their honeymoon to Scotland and England. In Leaskdale, she bought their first motorcar in 1918, and though she never learned to drive, she thoroughly enjoyed motor travel. She organized family outings to Niagara Falls, to the Kentucky Mammoth Caves, to Indiana to Ewan's brother's home, to Muskoka, and of course to Prince Edward Island. The Muskoka trip proved to be so enchanting that Montgomery broke her well-established pattern of using the Island as her setting, and set The Blue Castle in the Muskoka lakelands. For some years now, the Macdonald's arrival in Bala, Muskoka in 1922 is re-enacted and her happy holiday is celebrated at the Bala Museum.

Only a few of Montgomery's characters travel far or extensively. Anne Shirley Blythe and Gilbert go on a second honeymoon to Europe just before the outbreak of the First World War, but this is only mentioned and the novels do not take us overseas. Dean Priest, of the Emily series, goes on yearly travels to exotic places, but we learn almost nothing of these deliberately mysterious journeys. Similarly, Hilary Gordon, the hero of the two Pat books, travels to Japan to study architecture, but we do not go with him nor do we actually see Hilary's and Pat's house in Vancouver. Half of Jane of Lantern Hill is set in Toronto, but it is an unhappier half, and Jane and the reader look forward to the trips to the Island.

Montgomery's return to Prince Albert, Saskatchewan, in 1930 showed her just how much Canada had grown and changed. The latter parts of Montgomery's years are punctuated by trips home to the Island and excursions to do her many public readings.