Sailing into Casco Bay and threading between a number of small islands, you are welcomed to Maine’s largest town, and one of its busiest ports. The harbor bustles with fishing boats, cargo vessels and ferries coming and going between the mainland and the islands. The Old Port section, with cobblestone streets and a colorful fish market, is also a great place to wrap your hands around a fresh lobster roll, the quintessential summertime Maine treat. Stroll the Western Promenade for views of the river and the mountains, or the West End streets lined with 19th century houses. Further afield, there are no less than six picturesque lighthouses within 20 minutes of Portland.