Sign up for our Newsletter

The view from the Layla. (Photo Credit: David Benthal)

End of summer? Naaah, it’s the beginning of boating. The best time to float is here. August and September are prime-time for your water-based explorations, and the North Fork is surrounded by aquatic adventure on all sides, whether by motor, sail or paddle.  Here are some options for taking to the sea.

Take a narrated cruise to Bug Lighthouse

If you don’t own a paddle or boat shoes, all you need is two hours of calm weather on a Saturday night to go on a Bug Light Cruise with Bob Allen, great-grandson of the former lighthouse keeper. The Long Beach Bar “Bug” Lighthouse is the insect-like structure that can be seen from any East-facing vantage point in Greenport or Shelter Island. It was built to get mariners safely around a sandbar, just as the tour gets you and your fellow passengers safely from the dock at the East End Seaport Museum to the lighthouse, where you can disembark and take a look. On the way, you’ll see Greenport Harbor, Shelter Island and the most easterly part of the North Fork from a whole new perspective. Sailing dates are still available through September and can be reserved online. Bug Light Cruise and Tour, East End Seaport Museum, 103 3rd St. Greenport. Saturdays through September. $49/adults, $19/children for a two hour cruise.

Bug Light House. (Credit: Jeremy Garretson)

Book a private eco-friendly tour of Greenport Harbor

If you are looking to tread lightly on the environment as you explore local waters, pass up the stinkpots in favor of a vessel that has been operating on a battery since 1999. Glory, an environmentally friendly tour boat of antique design, runs on eight batteries charged by an array of solar panels installed on the roof of Preston’s at the Greenport waterfront.  Captain Dave Berson told me, “If the fish could vote, I’d be President.” Glory is a reproduction of a boat built for waterfront tours of an earlier era, and the back-in-the-day experience is part of what Glory delivers as she plies the waters of Greenport Harbor and Peconic Bay.  Glory is docked at Preston’s Dock, 102 Main Street, Greenport. Call 631-477-2515,  or visit $140 for a 45 minute private cruise for 4 people; $35 for additional adults and $20 for additional children, up to 10 people total

Live the yacht life without buying a boat

Vintage Yacht Kingfisher offers half-day, full-day, and multi-day charters out of Greenport on its beautiful 1959 50-foot Huckins Fairform Flyer. Each cruise is customized and can include extras like a private chef or tastings, said Dhardra Blake of Kingfisher Yachting and She called an escape on the boat “the closest thing you can come to time travel”: Last fall, they even created a “Some Like It Hot” experience with retro food, music and the guests’ attire evoking the 50s era of the movie. You can also buy an annual membership starting at 30 hours of boat time. Book through October via or call 813.484.5663. Prices on request.

Sail away for the day with the Layla

How about boarding a 45-foot sailboat for a day ride with a few of your choicest friends? Captain Liz Gillooly and the elegant ship Layla (a Fastnet 45, one of only 19 made) are ready to make that dream happen. Orient is Liz Gillooly’s hometown, and she knows the local waters intimately. A lifelong sailor and U.S. Coastguard Licensed Captain, she could get you across the Atlantic, but if your schedule doesn’t permit that, you can book anything from a two-hour sunset sail to a 6-hour full day circumnavigation of Shelter Island with stops at all the nicest beaches for a swim. You’ll feel like Cleopatra on the Nile. Layla Sailing, 1410 Manhanset Ave, Dock H4, Greenport, 631-319-0161. From $700 for a private sail with 6 guests.

Captain Liz Gillooly aboard the Layla. (Photo Credit: David Benthal)

Get some alone time out on a kayak

If your idea of bliss on the water is a journey under your own power, Shelter Island’s Marine Water Trail is ideal. Put in your kayak at the Burns Road Town Landing on Coecles Harbor, or rent one from Shelter Island Kayak Tours and spend a few hours paddling around the North shore of Mashomack Preserve, one of the most unspoiled waterways on the East End. You will see birds.  You’ll glide over jellyfish. If it’s not windy, you may have the kind of meditative experience that helps you sort out some things.  Get a map of the Coecles Harbor Marine Water Trail, and if you rent, call ahead and reserve a boat from Adam Mills at Shelter Island Kayak Tours, 80 Burns Rd. Shelter Island,  631-749-1990 . $60/adults, $30 children for a 2-hour guided tour; rentals from $30/2 hours.