With beautiful beaches, private chef lobster dinners, and a gorgeous mansion, Clapboard Island delivers a luxurious coastal escape.
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Aerial view of islands with sailboats in the distance
Credit: Courtney Elizabeth

Neal Kolterman first caught a glimpse of Clapboard Island, a private estate 20 minutes off the coast of Portland, Maine, in the 1980s. "The property just seemed to have this mystique, grandness, and privacy about it," Kolterman, who quietly admired the land from afar for 40 years, told Travel + Leisure. "I grew up learning to sail on the waters around the island and looking up at the large property always left me thinking, 'I wonder what that's like.'" I fully understood what he meant.

Not an hour before, I zipped over Casco Bay in a Parker sport cabin boat, headed for Clapboard Island myself with some friends and Neal as the captain. The forecast called for rain earlier that morning, but the August sun was doing a surprise dance along the blue surface as cool wisps of wind curled through my hair. The burbling acoustics of the boat made it somewhat difficult to hear one another, so we substituted conversation for smiles — after more than a year of separation and stagnation, it felt good to be moving, to be traveling with friends again.

Aerial view of estate house on Clapboard Island in Maine
Credit: Courtney Elizabeth

Before long, the vast bay, dotted with mainly sailboats up until now, was punctuated with something that appeared like a peaceful mirage in the distance. As we neared, the details became clear. First, the century-old oak and pine forest — wrapped around for an extra layer of privacy, I would learn. Then, the house, a stunning, 124-year-old mansion that managed to look both warm and luxe, if even for a moment — the property revealed itself for an instant before taking cover behind the blanket of trees once again. The ephemeral view left me thinking, like Neal all those years ago, "I wonder what that's like?"

Fortunately for my friends and me, we were about to find out. The plan: Spend a day on the 22-acre private property, picnicking on the beach, devouring buttery lobster rolls, walking the many trails, and generally living out a faraway fantasy of calling an island ours, and only ours.

Water shoreline with trees and rocky cliffs and hills in the distance
Credit: Carley Rudd

Clapboard has an untouched, almost surreal feel: Picture six wild beaches; pockets of pink, purple, and yellow blooms; a wooden dock curving out into the water; and Adirondack chairs lined up one by one on a grassy lawn, perfect for taking in the sunrise or sunset. With plenty of idyllic nooks to wander and get lost, it's hard to pick a favorite. For Kolterman, though, it's got to be the beach by Little Clapboard Island, part of the main property that's reachable via a sandbar at low tide for picnics and afternoon swims. "The water in the small 'punch bowl' gets warmer than the surrounding waters and makes for great swimming, and it has sunshine all afternoon," he said. "Another favorite is West Veranda — it's the go-to spot for evening cocktails and to watch the sunset."

All of this and more lies a short boat, water taxi, or schooner ride from the breweries, shops, and restaurants of Portland. For mere mortals, anyway — there's a helicopter landing area for those wanting and able to drop in.

Chic outdoor chairs and umbrella set up for picnic on Clapboard Island
Credit: Natalya DeSena

Still, the most exciting draw might be its location. "Guest can experience the remoteness and privacy of an island without having to the go to the end of the Earth," said Kolterman. "We like to say, 'away from the world, but minutes from reentry.'" As the surrounding cities and islands swell with crowds in the busy fall and summer seasons, Clapboard stays deliciously quiet. "The island has remained a large and undeveloped property for the last 125 years," he added.

But the same can't be said about the house, which had previously been in "disrepair," according to Kolterman, who led the restoration from top to bottom — a complex endeavor on its own, no less on an isolated island. (His family, who now owns the place, bought it in 2018.) Built in the 1890s by a Philadelphia railroad owner, the property in its current incarnation has 13 bedrooms, each with views of the bay; nine bathrooms; a dreamy chef's kitchen; lots of places to cozy up — from the gorgeous dining room to the living room with plush couches and fireplace; and my favorite, a spacious deck with the bucolic grounds and bay sprawled before it.

Patio seating at estate house on Clapboard Island in Maine
Credit: Natalya DeSena

Inside, the décor leans coastal, with bright whites, warm woods, and lots of natural light. It's an update with contemporary appliances for sure, though Kolterman chose to keep, rather than replace, some of the original details, including the handmade glass windows. "Every window sash was removed from the house and shipped ashore. Each of the 1,800 panes of glass were painstakingly removed, sashes steamed to remove lead paint, and then reassembled and reinstalled into the house," he said.

Clapboard doesn't need a pitch as a romantic getaway for couples — the grounds, the house, and the views are a testimony in and of themselves. But it's an ideal hideaway for families, too. "All of our guests have one thing in common: They want privacy, space, and safety with access to the ocean and spectacular views," said Kolterman. But, of course, they get much more than that. Kayaks, paddleboards, picnic areas, walking paths extending 40 acres into bordering conservation land, and even a zip line are among the amenities. The team can customize each stay based on guest preferences, whether that means arranging a small boat day sailing, waterskiing, and wakeboarding, or transfers to a neighboring island golf course.

Guests can also choose to have the home fully provisioned in advance of their arrival, and book a private chef, from dinner every other night to full service three times each day.

"As for activities, the sky is the limit — literally," said Kolterman, noting a sea plane tour of Acadia National Park he once arranged. Other things to do include guided fishing trips, lighthouse tours, boat rentals to nearby islands for hiking — all starting and ending on the island. If you prefer to stay on the island itself, there are options galore as well, including outdoor movie nights on the lawn, lobster bakes on the beach delivered by a local lobsterman, live music, and scavenger hunts.

Interior guest bedroom at Clapboard Island Estate in Maine
Credit: Courtney Elizabeth

If you want to get away from, well, everything, this is the place to do it — while here, the everyday pressures of life simply fade, and what you're left with is something that resembles nirvana. "The island has been off the grid since before there was a grid," said Kolterman, who further explained that during the summer, a solar array powers everything. That said, there is Wi-Fi — and a strong signal at that — though with so much natural beauty to appreciate, this fact feels almost unnecessary. Rather than remaining glued to our screens, it was easy to fall into an unhurried tempo here, enjoying languid lunches and afternoon beers on the porch; taking a leisurely stroll down this path, then that, watching for seabirds overhead; sitting on the beach staring at the tide coming in and out and in again, pulling a blanket over our knees when the sun started to fade and the coastal breeze came in; and simply enjoying the company of good friends.

Once we returned to the city, we took some of this solace with us. Excitedly telling friends and family at home how we had spent the day, they, too, were intrigued by the secluded island, "wondering what that was like." The reality is that it exceeded all expectations.