Cross Parasailing off Your Bucket List with Block Island’s Captain Littlefield

On a clear day on Block Island, you don’t have to be in an airplane to catch a glimpse of four states at once – New York’s Montauk Point, the shores of Connecticut, mainland Rhode Island, and Cuttyhunk in Massachusetts are all visible when you’re floating aloft on 800 feet of line attached to captain Robert (Bob) Littlefield’s winchboat.

“Everybody expects parasailing to be something that it’s not,” says Littlefield, who owns and operates Block Island Parasail for a bustling yet fleeting eight-week season every summer, launching around 40 people each day during busy weekends. “It’s not like jumping out of a plane. As you’re clipped into the chute and we start to pick up speed in the boat, you gently lift off of the deck and then you’re slowly reeled out, so you’re actually sitting still and the boat is going away from you. It’s actually kind of relaxing.”

Littlefield grew up on Block Island and used to parasail off the beach as a kid, but the invention of the winchboat, a self-contained parasailing vessel reeling passengers up into the air and safely back onto deck, was a game changer. “Back in the late ‘80s, early ‘90s, it was just becoming a big thing at all the island resorts,” says Littlefield. After witnessing the phenomenon while vacationing in Hawaii in 1988, he knew he needed to introduce the craze to his home island. He didn’t waste any time in purchasing a winchboat, going before the council, and opening Block Island Parasail – which celebrates 35 years this summer.

“My business is all about families,” says Littlefield, explaining that he’s flown young kids who have come back as adults with their own children. “One lady from, maybe it was last year or the year before – the screensaver on her phone was her when she flew with her dad. She was five.” His youngest parasailer? “My nephew was six months old and he flew with my brother.” His oldest passenger was 94, and Littlefield has even made it possible for wheelchair users to take flight.

While it’s not for everyone, parasailing isn’t just for thrill seekers, either. “I actually fly a lot of people who are afraid of heights, and it doesn’t bother them because of the fact that they’re over the water, and it really is a different perspective,” says Littlefield.

Banana boating, on the other hand – “That’s a little crazier than parasailing,” says Littlefield, who offers the group rides towed by his 23-foot competition ski boat. “It’s kind of like white water rafting on the ocean. All it takes is one person to lean incorrectly and it will flip the whole banana over. With that kind of ride, you’re going to get wet; you’re most likely going to fall in the water.” The 10-12 miles per hour feels more like 30.

Whether aboard a banana or drifting from a parachute, safety is top priority. Despite falling in love with parasailing early on, Littlefield is never strapped into the harness himself anymore for one simple reason: “I’m the only one that’s ever captained the boat,” he says. His many years of experience and knowledge of Block Island’s fickle weather patterns allow him to make sound judgements on and off the water.

But Littlefield doesn’t miss taking to the air, and looks forward to returning to Old Harbor Dock every June. “It’s a great job because you’re making memories and you’re making peoples’ vacations.”