In the early 20th century, Maine was a haven for city dwellers across New England and beyond. The sound of the ocean soothed the noisy minds of the fortunate "summer people" who vacationed on the idyllic coast or on one of its many islands. Southern Maine's Casco Bay hosted many visitors for part, if not all, of the summer. The Casco Bay Breeze, a "summer paper" provided news for the residents and visitors alike at a cost of 5 cents per issue. The Breeze was heavily laced with reports of social gatherings, visitors, festivities, and controversies of the islands. It served many of the adjoining communities including Little Diamond, Bustin's and Cousin's islands, as well as the nearby towns of Harpswell and South Harpswell.

Columns for each of the islands focused on tourists, summer residents, and their visitors. The popular inns and hotels, including the Peaks Island House and Aucocisco House, issued regular reports on the comings and goings of guests including their home towns and reasons for their visit.

Stories of fires, shipwrecks, and island squabbles and celebrations regularly filled the pages of the Breeze. The size of the paper fluctuated depending on the season and amount of news fit to print. Typically, it was an eight-page weekly, which swelled to 16 pages at times for the "Souvenir Issue."

Stores from the mainland of Portland advertised "summer goods" for sale such as cameras, film, books, magazines, pens, and stationary. Others pedaled provisions such as paint, oil stoves, home furnishings, and groceries. Cottage caretakers, plumbers, building contractors, transporters of luggage, and others also drew attention to their services, which they provided both to tourists and to summer visitors.

As the automobile gained popularity, advertisements appeared in the Casco Bay Breeze for passenger service or excursions by Packard cars or the like. Entertainment was a frequent source of news. The islands offered many concerts, plays, festivals, and sailboat races during the warm months, and the Breeze gave lively accounts of these events. On September 3, 1914, for example, a front-page article told of a "Brilliant Party" held on Chebeague:

At Assembly Hall, the regular weekly entertainment was omitted and a masquerade party arranged for Thursday evening. The affair was quite impromptu and many who might have been conspicuous by their absence caught the spirit and even at the eleventh hour got interest and were present in costumes.

The Casco Bay Breeze appeared weekly during the summer months and monthly throughout the rest of the year. Crowley & Lunt of the Breeze Publishing Co. printed and distributed the Breeze in South Harpswell and Portland between 1901 until 1917. Crowley & Lunt also published the "Casco Bay Directory," a resident, business, and summer resident directory for the Casco Bay region.