Treat yourself to the best boat charter Portland, Maine has to offer with Sail Portland Maine. There is no better way to experience our vibrant city’s coastline!

Relax aboard our sailing vessel the Eleanor Hawkes, or our newly acquired picnic boat, the Calista Ann, as we cruise through tranquil waters of Portland Harbor sailing Casco Bay. Bring along any beverages and snacks you want, there are a myriad of eateries, breweries, and food trucks in Portland. Come enjoy the sights and sounds of our lovely Casco Bay and the Portland skyline and working waterfront.

Create Memories That Will Last Forever with Sail Portland Maine!

Whether you are visiting Portland for the first time with friends, on vacation with the family, or looking to surprise your significant other with a proposal or anniversary gift. Sail Portland Maine will provide you with the best experience on the water. Your time and enjoyment is of the utmost importance to us – we will do everything to make your time in Portland and sailing Casco Bay a memory you’ll talk about for years to come.

We Offer Unique Boat Trips

We can create a custom boat charter in Portland, Maine to fit the mold for whatever it is you’d like to do. Do you want to sail to an island for dinner such as The Crown Jewel on Great Diamond Island? You can then take the free ferry home, or charter the boat for the whole evening and cruise home under the stars.

Do you have a group going out to a wedding on one of the islands? Want to arrive in style, or have a unique boat for photos, our picnic boat can bring you there. Want to sail to an island where you’re staying instead of taking the ferry there? We can host elopements where the captain is the officiant, or bring your own. Add a photographer and a few friends to create a small memorable wedding. We are also happy to take you sailing longer than two hours – up to eight hours for an all day sail!

Let Sail Portland Maine make your trip to Maine a lifelong memory!