As it turns out – and I mean this is just dumb luck – we live in a spot that is characterized as the “best sea kayaking on the east coast” by online forums. Stonington is a little fishing village, and it’s surrounded by over 60 islands. This archipelago is “to die for” if you are a kayaker.
For over 20 years, the most popular place to go kayaking on Deer Isle was Old Quarry Ocean Adventures. Old Quarry offered guided tours, rentals, camping, sailing and was an incredibly popular spot. Their customers came year after year. I met some people who had camped there 12 years in a row. It was located right on Webb’s Cove, across from where we live, so when my son Will decided to work there, it seemed like a great idea. He could drive there from our house in 5 minutes or kayak across the cove to get there in about 10 minutes. Will worked there for several summers, got his kayak guiding license and was eventually promoted to head of waterfront operations. The guide license process is no picnic in the state of Maine – you need to pass written and oral examinations that inspect your knowledge of kayaking, safety procedures, navigation, wildlife (he had to learn about over 40 birds). It was a feather in his cap to get the license at age 22.
And then it ended. The owner of Old Quarry decided that after over 20 years of it, he’d had enough and put the place up for sale. It was an agonizing summer – we hoped that the local heritage trust would buy it and keep it open for customers. Eventually a wealthy person from New Jersey bought the property and the island lost an important small business. They closed in early July of 2019 and for the rest of the summer, people grew frustrated – there are not many places to launch a kayak, other than the town ramp. It became a real issue for the town, and the town ramp became a real shit show – everyone wanted to put in from there. Two companies decided to operate from that town ramp, renting and conducting tours. During the pandemic, going to Maine and going out kayaking became a popular activity.
Will finished the summer of 2020 working as a guide in Bar Harbor. Acadia is beautiful and has some amazing hiking…but the kayaking is nowhere near as beautiful and interesting as in Stonington. Will finished the summer – taking customers on the same route day after day, around the one island that is close in. Then he said – “I want to start my own business, here in Stonington.”
Will knows a lot about kayaking. Starting and running a small business is a bit more complicated, though and he asked for help. We needed to put together a business plan, build a pro forma P&L, source capital for boats (guess where 😇) and developing a marketing plan. The good news – Will has a family full of expertise to tap into. He created his “Board of Directors” and began the plan. Firstly he needed a name for the company. Mom had named our house Osprey’s Echo, so it was pretty straightforward to call the new company Osprey’s Echo Sea Kayaking. We filed paperwork to make it Osprey’s Echo Sea Kayaking LLC in Augusta, Maine. ta-dah!
Next – we needed a place to conduct business, and launch kayak tours. He asked us for permission to operate from our property and with a little trepidation we agreed. We made a beautiful wood-chip lined path through the woods to a clearing where he could launch tours. We were in no position to rent kayaks, but could conduct tours,
Big Sis happens to be a professional in Marketing, as head of Social Media for the ski company Alterra (ikon pass, anyone?). Other big sis is a banker, living in London and with very useful expertise when it comes to managing a P&L. Big brother is at medial school, so not bringing that expertise to bear, but has been a great help in a number of other areas – contributed swag (sweatshirts for the whole Board), a way cool laser-cut-out-of-sheet metal company sign (check it out) below. His buddy even designed our company logo.

Mom and Dad help wherever needed, of course – hauling boats, answering phones, booking customers, greeting customers, washing gear, you name it. I added the title Chairman, Ospreys Echo Sea Kayaking LLC on my LinkedIn profile (self-proclaimed of course), and you wouldn’t believe how many messages I received, congratulating me on my new position.
It turns out that Will is very good at this. He pays attention to detail when it comes to the business, and he’s excellent with customers on the water. He studies the history and culture of the island and is prepared to share stories with visitors, who love it. He’s been to pretty much every island out there (and there are over 60) and can plan a different route every day – so much better than up in Bar Harbor.
This is year 2 of the business. We got lucky and procured a piece of land nearby that while tidal, is convenient for launch at any time. Low tide just means a longer carry of the boats. As year 2 comes to a close, it looks like he will have doubled his revenue and # of customers from year 1, even without a second guide. Even better, we have over 100 Tripadvisor ratings and another 50+ google ratings, ALL of which are 5* and very flattering.
Bottom line – we are helping fill a bit of the gap left by Old Quarry, have created a viable business that people seem to value, and it’s fun!
We shall see where he takes it next.