The Work We Do: Liz Gillooly, Captain of Sailing Vessel Surprise

My name is Liz Gillooly and I am the captain of Sailing Vessel Surprise and I run charters out of Greenport.

I got into sailing when I was 8 years old at the Orient Yacht Club. That’s when I first learned how to sail.

Then, when I was 20 years old, I sailed down to the Caribbean. I was offered a crew position on an 80-foot racing maxi and it sounded like a pretty awesome adventure, so I decided to hop on a boat leaving from the dock right by Preston’s. We sailed from here down to Bermuda and then down to Saint Martin and to the Virgin Islands. I was supposed to just take six months off school, and I ended up staying down there almost four years, working on sailboats.

Captain Liz Gillooly. (Credit: Kelly Zegers)

My day starts about an hour and a half before the sail. I come to the boat, I do an engine check. So I check oil levels, transmission fluid, coolant and just a general check of the engine. And then I primp the boat and get it ready. And then we single up all the lines so just one side has lines for when guests arrive.

When they get here, we board everybody on the boat and then we go out sailing. Sometimes we’ll sail all the way around Shelter Island. Other times we’ll just go out to Orient Beach State Park or Jessups Point and we’ll drop an anchor and let people swim for a little while. So it’s kind of different based on whichever group we have.

This was my second summer working on Surprise. We’re kind of wrapping up now, working until the end of September.

Greenport is traditionally a big sailing port. I grew up in Orient, which is originally a whaling port. To go out sailing on boats is sort of what our whole history is about. So we’re sort of keeping that alive out here and keeping the boating community alive. We have a huge nautical background and we have a lot of history with wooden boats and building boats around here. So to be working on a 50-year-old wooden boat in Greenport, that’s an amazing way to keep the tradition alive.

‘The Work We Do’ is a Suffolk Times multimedia project profiling workers on the North Fork. This weekly feature is made possible by Peconic Landing. See more photos on Instagram @thesuffolktimes.