Portland Sailing Charters

Portland's prime location on the ocean overlooking the islands of Casco Bay means that many of our guests want to get out on the water when they visit our boutique hotel Pomegranate Inn. Fortunately, there are several great options for Portland sailing charters that combine a trip on the water with education, sightseeing, and even drinks. Check out these three options for Portland sailing charters and cool off with an afternoon of boating.

Our Tops Picks for Portland Sailing Charters

Portland Schooner Co. | Maine State Pier, Portland | (207) 766-2500

These two schooners docked on Portland's working waterfront offer several sails daily. Enjoy a two-hour scenic cruise on these beautiful historic wooden schooners, where you can help raise the many sails (or not!) and then sit back and relax as you go where the wind takes you.

Casco Bay Lines | 56 Commercial Street, Portland | (207) 774-7871

It may seem strange for us to recommend a public ferry as a Portland sailing charter, but hear us out. The mail boat run, offered daily at 10am and 2:45pm, takes about 2-1/2 hours and visits 5 islands while offering a narration about the history of the area (and yes, the boat actually delivers mail to island residents and businesses). Bring your own picnic and beverages (alcohol is allowed) and make a day of it.

Maine Sailing Adventures | Maine State Pier, Portland | (207) 749-9169

The Frances, a 90-foot sloop with a wide-open deck, offers sails around Casco Bay daily. Because the boat is so wide, it offers a nice comfortable ride for anyone who might be nervous about the way sailboats heel or tip while sailing. Our friend Erica Archer of Wine Wise partners with Maine Sailing Adventures, offering educational wine sails which are frequently paired with oysters.

Whatever Portland sailing charter you choose, you're sure to have a great time enjoying the views and weather of Casco Bay.