Meet Our Boats
Discover our growing fleet of vessels, each tailored for a unique sailing experience. Whether you're looking for an intimate gathering or a larger group adventure, we have the perfect boat for you.
Choose Your Vessel
Join Sail Portland Maine for a more intimate trip around the waters of Casco Bay aboard our 6 passenger sailing vessel, the Eleanor Hawkes, or our 12 passenger Classic Motor Yacht Picnic Boat, the Calista Ann.
Read on for more details and photos of these two magnificent vessels.
Eleanor Hawkes
The Eleanor Hawkes is based on the Friendship sloop, also known as a Muscongus Bay sloop or lobster sloop, which is a traditional style of gaff-rigged sloop that originated in Friendship, Maine around 1880.
Fishermen in Friendship and neighboring Bremen collectively originated the design, one influenced by the fishing sailboats of Gloucester, Massachusetts, particularly the schooner Fredonia of 1889.
Although familiar as a pleasure craft today, the Friendship sloop was the traditional fishing boat used off the coast of Maine, especially for lobstering, until the introduction of the gasoline engine early in the 20th century. Friendship-area boat builder Wilbur A. Morse produced many examples from the 1880s and into the early 1900s.
Calista Ann
The Calista Ann is our newest addition to the Sail Portland Maine fleet! This motor vessel, also sometimes referred to as a picnic boat or cocktail cruiser, has slightly more seating and space to move about, so if you’re looking for a private cruise for a larger party, Calista Ann is the boat for you!
We offer cruises for up to 12 guests on public and private charters to keep the intimate feel for your group. We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule. You can see all our available charter times here!
Book Your Sailing Tour in Portland, Maine
Come enjoy a trip of a lifetime on the most unique boat tours Portland Maine has to offer. Book your charter with Sail Portland Maine today!