Flying High Above Montauk

Up in the air with a smile with Montauk Parasailing. Madeline Hinderstein photo

Montauk isn’t exactly the first place that comes to mind when you think of going parasailing. Tropical or destination areas such as Caribbean Islands or Mexico are more known for having this bucket-list activity, but Captain Joe Rahill of Montauk Parasailing will bring you to new heights that you’d never expect to find on the East End. Venture outside of the crowded town of Montauk to the Star Island Yacht Club and Captain Joe will take you and up to 12 people on his boat for a parasailing adventure.

As soon as you arrive at the dock, all responsibilities are off your shoulders. Captain Joe says his team strives to make your experience easy and enjoyable. Shortly after leaving the inlet and entering the Block Island Sound, you’ll be strapped into your harness and life jacket. Once the sail is prepped and ready, participants sit on the back of the boat and are safely hooked onto the sail via their harness. Once the speed kicks up, it’s time to fly.

Flying at either 500 or 1,000 feet in the air, it is possible to take in almost the whole of the East End, from Orient Point to Montauk. Quietly gliding over the Block Island Sound and Shagwong reef, it is possible to take in views of New York, Connecticut and Rhode Island.

Landing is just as easy as taking off. As you’re lowered down you can opt to get your toes dipped into the water or get a quick dunk before safely landing on the stern where you started.

Montauk Parasail offers various times of the day for parasail experiences with each time of day having its advantages. The “early bird” times, 8am and 9am, are when the water is the calmest and you’ll be able to see the most fish from the air. Afternoon trips are the most common and the last trip of the day is an adult happy hour, featuring a sunset cruise of the Montauk Harbor.