Our Story.
When I was a kid, I’d sail the clumsiest sailboat you’ve ever seen from my grandmother’s dock in Harpswell to nearby islands to camp alone. There was something about the solitude, peace, and collaboration with nature. That love for the ocean and exploring Maine’s amazing coastline never left me and I now live aboard my own full keel cutter, Cormorant, spending my weekends doing what I loved to do as a kid.
While captaining charter boats in Portland, the longing for that same solitude in locals and visitors alike became more apparent. People want to explore the coast in a different way, not crammed onto a narrated tour, but freely, like a child on his clumsy boat feeling like he’s discovering new islands for the first time. Cormorant is your boat just as much as mine and I hope you feel that way during your sail with us.
- Capt. Jacob
Where do we sail?
For the 2026 season, we'll be focusing on a limited number of charters in the Penobscot Bay area, home to more than 200 islands and some of the best cruising grounds on the east coast. We'll be departing from Southwest Harbor, MDI, bound for a few of our favorites including Hen, Green, Hell's Half Acre, Little Black, and Buckle where you can hike, camp, sunbathe, swim and soak in the beauty of Maine.
Thanks to Maine Island Trail Association and the Maine Coast Heritage Trust, we're able to enjoy these islands and help steward them to ensure future generations can as well. Cormorant Sailing Co. is a proud partner with MITA, and together with you, we can do our part to pick up any trash on these islands, participate in organized cleanups, and help protect precious wildlife and nesting grounds.
Penobscot and Jericho Bay (July 6th - Aug 30th)
Via Southwest Harbor, MDI
How far will we go?
To give you a better idea of where we're able to go with the time we have together, below is an interactive map roughly outlining the area and islands we can cover for each trip booked with total possible sailing time. These are, of course, subject to change depending on weather, the comfort of the crew, and your interests.
There are no set routes as we are dependent on the winds and tides. But that's part of the fun of sailing, working with nature toward an unexpected adventure.
Day
3-6 hrs
Overnight
6-12 hrs
Weekend
12-18 hrs
Hell's Half Acre, Bold, Devil Islands
Green Island
Duck Harbor, Isle au Haut
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Potato Island
Weir Island
Wheat Island
Buckle and Hen Islands
Tinker Island
Little Black Island
Hurricane Island
Little Hen Island
Interested? Learn more about our trips below
"Now, more than ever, we need a place like the Maine coast, where life is reduced to its bare elements: the rise and fall of the tides, the shift of the wind, the call of a loon, or the impossible appearance of a leviathan rolling out from the deep. We come for the smell of sun-warmed water, the safety of a secure anchorage, the feeling of soft moss underfoot, or the sound of the breeze in the spruce. We come here for something fundamental.
Fortunately, we have come to the right place. We come because the raw, uncompromising beauty and power of the Maine coast help us recalibrate our sense of what is and what is not important. We come to speculate on our purpose or our insignificance, or both. We come because the coast’s scale and timelessness reduce us to the momentary sparks that we are and at the same time jolt us with knowing that we are blessed to be a part of it all."
- Hank and Jan Taft, A Cruising Guide to the Maine Coast