Steal away to New England’s most luxurious island—you’re only a hop, skip and a heli away from true bliss.
An aerial view of the island.
Imagine this: You’re sitting on a secluded beach—small waves lap on the shore, and the smell of fresh baked lobster wafts under your nose as a pink sunset illuminates the water. There are no crowds, and your every whim is fulfilled. This is the reality of Clapboard Island Estate (clapboardisland.com). Located just off the shore of Portland, Maine, and a short two-hour drive from Boston, the 125-year-old retreat puts an end to private island treks via seaplane. Quickly jet off to an emergency meeting in the city or explore the mainland for a change of scenery—as owner Neal Kolterman says, the estate is “away from civilization, but minutes from reentry.” Owned by various prominent families over the last century, Clapboard Island was transformed into a New Englander’s dream escape from 2020 to 2021 and welcomed guests for the first time last summer. Kolterman has coveted the island for over 40 years. “It’s a property that I’ve had my eyes on since I was a little kid learning to sail on the waters around the island,” says the Portland/Falmouth native. Now, guests are invited onto the private shores May through October for week-long-plus vacations of luxurious leisure. Travel by boat or helicopter—the choice is yours. Upon arrival, VIPs are ushered to the chic, restored home that sleeps 16 or more people. Draped in Nantucket-style cedar shingles, the house retains a historic, beachy feel, calling on its rich past of hosting elites like former U.S. presidents and other affluent families. “We restored as much of the original features as we could and really brightened and gave it more of a coastal, fresh feel versus the dark turn of the century look that it had when we purchased it,” he notes. Once settled in, the vacation is completely customizable for an additional price. Have a picnic or lobster bake (with fresh-caught crustaceans from a local lobsterman), charter a boat ride, schedule a yoga class, melt away in a massage or personal training session, go paddleboarding, zip lining, kayaking or biking—the possibilities are endless. Prior to the escape, arrange everything with the team—such as private chefs (think former White Barn Inn chef Derek Bissonnette and pastry chef Gabrielle Cote), staff, provisions and activities—or bring your own along if you wish. The estate is comparable to a villa rental or chartered yacht where solitude and access to anything one desires go hand in hand. “Because it is isolated, we like to say the island is like a ship at sea since we are completely independent and self-reliant in terms of power generation, water and maintaining things,” Kolterman shares. “You have that remote feeling of your own sanctuary with 22 acres and your own beaches and ocean views from every room.” During the estate’s pandemic opening, when no one sought out packed vacation towns and resorts, Clapboard Island was the answer to many people’s prayers. And not too much has changed post-pandemic, as more families and couples seek private trips where traffic, packed beaches and overbooked restaurants are a distant memory. “People can have a similar oceanside experience without all the crowds, and that’s a big point for a lot of our guests,” Kolterman says. “Places like Nantucket are great, but on a Friday night, it’s a mob scene.” As the glorious getaway opens for the season this month, consider the possibility of a true vacation. “It’s magic,” Kolterman explains. “When you step onto the pier and walk the grounds, you’re surrounded by seabirds and seals around the island, multiple antique gardens and walking trails. The serenity of the place really speaks to a peaceful and relaxing escape from everything, and I think a lot of people want to get away from the world right now.”
Awaken to the morning light in one of the house’s sun-filled bedrooms
Photography by: Courtesy of Clapboard Island Estate; Photo Courtney Elizabeth Media