Due to state regulations related to COVID-19, we will begin guided boat trips beginning on May 22, 2021. If you are uncomfortable with being on a boat with other members of the public, a private charter is always an option aboard our vessel. Masks will not be required since the boat is not enclosed, but they are encouraged based on passenger comfort. Sail Portland Maine will provide masks for you to use on-board and take with you after the trip. We will also provide hand sanitizer as well. All cushions and railings will be sterilized before each trip. Our policy has always been BYOB, which remains in effect for your convenience and safety. If you have any questions or concerns, please don’t hesitate to reach out!


Sail Portland Maine Aboard the Eleanor Hawkes!

Treat yourself to the best views the city of Portland has to offer with Sail Portland Maine. You can relax and unwind aboard our sailing vessel as we slip through tranquil waters. Bring along beverages and snacks. Come enjoy the sights and sounds of our lovely Casco Bay and the Portland skyline.

Create Memories That Will Last Forever

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, we here at Sail Portland Maine will provide you with the best experience on the water. Your time and enjoyment is of the utmost importance to us and we will do everything to make your time in Portland a memory you’ll talk about for years to come.

We Offer Unique Trips

Want to sail to an island for dinner and take the free ferry home, or charter the boat for the whole evening? Want to sail to an island where you’re staying instead of taking the ferry there? We can host elopements where the captain can act as the officiant, or bring your own and a photographer and a few friends to create a small memorable wedding. We also will be happy to take you sailing longer than two hours and can suggest places to grab food for the long trip. Let Sail Portland Maine make your trip a lifelong memory!