From Jamestown to Edgartown, Kennebunk to Cape Cod, these Bostonians soak up the sun with their own spirited culture, history, and glamour.
Kathy Burns and Michael Greeley playing croquet with their children.
We could tell you where this house is, but then we’d have to kill you. Here are some hints: It’s in Maine—Kennebunk, to be specific, and on the beach. That’s all you get. Kathy Burns spent every summer on this beach while growing up, and her great-great-grandfather built the house. It is super private, and her oodles of relatives want to keep it that way. Who could blame them? This is Maine at its most pristine. Kathy, a veteran hotel acquisitions executive, credits her hospitality career for lighting up the property with just the right kind of wild parties mixed with always-time-for-a-kayak-ride family time. For her venture capitalist husband, Michael Greeley, the “Big House” became his home, too, the day they got married there. Now with a son and daughter, the couple continues the family legacy.
What do you love about your house?
MG: If a house could be like Cheers, this may well be it, although, admittedly, there have been mornings in the kitchen when I don’t necessarily know everybody’s name.
Do you have any annual traditions?
KB: We love to put together eclectic groups of houseguests for weekend events and dinner parties.
MG: For years, we hosted a spectacular series of weekend activities for a few hundred friends, which culminated in a themed costume party. This is a house made for entertaining.
What are your fondest memories?
KB: Catching over 60 mackerel with my dad after launching our little boat in the surf when I was 10 years old. Climbing the rocks was always special. Now I get to do that with my kids.
How do you spend family time?
KB: We love clam and lobster bakes on the beach. We gather around the fire pit under the stars.
What does the future hold?
KB: I want my kids to cherish the same things I did as a kid—surfing in the cold Maine ocean and working in Kennebunkport with everyone from lobstermen to summer residents.
MG: The house is incredibly grounding for our family. I want my grandchildren’s grandchildren to be able to enjoy it and share it with their friends.
Catching a chicken on the front lawn.
If you bumped into Christy and Jay Cashman at their chicken coop on Strong Island, you would probably—no, make that never—guess what their “real” life is. She is a glamorous filmmaker and actress; he is a master-of-the-universe, general contracting business owner and inventor—Monday through Friday, that is. Summer weekends consist of tending to the garden, hatching chicken eggs, midnight golf cart rides with their children (four between them), and a constant flow of friends. But make no mistake: This is no country farm. It’s 200 acres of woods, salt marsh, and beach, with hundreds of species of birds, room for horseback riding, and six different varieties of clams. The chicken coop is just the beginning…
Why did you choose to set up shop on Strong Island?
JC: I lived on Middle Brewster Island when I was a kid with my family for two summers. Although we were camping and roughing it, I remember those summers as the best of my youth.
CC: It was obvious the minute I set foot onto the poison-ivy-ridden, bug-infested land that it was a special place. I loved the wild, unruly landscape.
What summer culture have you created as a family?
CC: I love that we are eating vegetables from the garden minutes after they’ve been picked. And starting the day outside in the barn with all of the animals, and ending the day outside watching a movie on the outdoor screen in a sleeping bag.
JC: The culture is welcoming to our friends. There is always a spare bed.
What are some of your favorite activities?
CC: I love my chickens. Riding the horses on the beach… piling everyone on the pontoon boat, kayaking around the sometimes shark-infested waters, and, of course, campfires.
JC: Playing beanbag, bocce ball, tuna fishing, boating to the other end of the marsh (known as the party point).
Do you have any special traditions? CC: Well, we have quite a few parties, planned and unplanned. We might wake up and it will be just Jay, the boys, and me. Then a call comes in from friends who are passing through Chatham, and we pick them up in a boat. Then another call comes in, and suddenly we have a house full of friends.
Lucy, Wyatt, Patrick, and Kristina Lyons on the oceanside cliff.
If you don’t know Kristina and Patrick, you really ought to figure out a way to get on their good side. Seriously, this couple can party in an epic way. Part of it comes with the package that is Patrick Lyons, the king of Boston nightlife, whose company, The Lyons Group, has dominated Lansdowne Street for decades as well as spawning national chains such as Summer Shack, Kings Bowling, and most recently, Blazing Paddles, a ping-pong club in Fenway Park. Kristina holds court as the co-owner of Portobello Road, a hip women’s boutique in Chestnut Hill, as well as being an aspiring filmmaker. No surprise, then, that their summer house on Martha’s Vineyard routinely bursts at the seams with uproarious dinner parties, Hollywood guests, and just-one-more-swim energy. It’s in their DNA.
How did you come to summer in Martha’s Vineyard?
KL: Patrick had a little place in Oak Bluffs and invited me for a long weekend when we started dating. It was my first time to the Vineyard, and I just fell in love.
PL: I love the diversity. It’s rural and farmlike in Chilmark, bordering on honkytonk in Oak Bluffs, and everything in between.
What is special about your house?
KL: Our location! It’s so wild to be on a cliff overlooking the Atlantic.
PL: Sometimes a house owns you, but we built our house so it was simple and functional. We definitely own it.
What atmosphere have you created?
KL: Very relaxed. Very inclusive. So many kids running around it’s like summer camp. Lots of grilling fresh fish that we pick up in Menemsha and pizza-making in our outdoor pizza oven.
PL: It’s beach by day, tennis in the afternoon, and fish caught that day by a friend for dinner.
And when it’s just the four of you…
KL: The kids are in the pool, or we’re piled together watching movies, playing poker games, or lying around on the window seats on a lazy day reading The Vineyard Gazette.
Do you have any traditions?
KL: We have a big come-one-come-all potluck dinner at the end of the summer. Patrick makes paella outside on the fire pit. For the Fourth of July, we go to the Edgartown parade and throw candy to the crowd.
PL: We throw one big bash every summer. We invite all of our regular Vineyard crew: Larry David, Jim Belushi, the Farrelly brothers, Dick Friedman, and all of their families, and everyone else we know.
What will future summers bring?
KL: I hope it will continue to be a place where friends and family come together. The cliff has very special mystical energy. Everybody says that.
Roy Schoenberg at the wheel of Latitude.
We can safely say that Roy Schoenberg knows the difference between port and starboard. He didn’t in the beginning, but he does now. Good thing. He owns pretty much the farthest thing from a starter boat—a full-throttle-or-bust, 35-knot (that’s fast!), 64-foot-long Azimut yacht named Latitude. After growing up and becoming a doctor in Israel, Schoenberg came to Boston and earned a master’s degree in public health at Harvard Medical School, but switched gears to start American Well, the nation’s largest telehealth network. The workdays are intense—24/7, says Schoenberg. But after finding Latitude, his weekends are bliss: motoring to Newport, Nantucket, Martha’s Vineyard, Block Island, the Hamptons—anywhere, really, that Captain Schoenberg fancies. Land ho? No.
How did you find Latitude?
When I was in Nantucket, I saw a beautiful boat. I went to the dealers and said, “Listen, I have no clue about boating. Help me to get to the point that I can get a boat. Long story short, I am completely addicted to boating.
What is special about the boat?
It’s smiling if you look at it. It has a personality. It wants to run on the ocean more than you do.
What is it like to live on the boat?
One of the amazing things about boating is that it can be a completely different world from one day to another. One day, it’s you and close friends and smooth sailing to a secluded place, sitting on the flybridge, feeling the breeze. Then, on another day, it’s 35 people in bathing suits, dancing up and down and jumping in the water. The beauty is that people change when they are on a boat. This isn’t about showing your wits or knowledge or how much money you make. You can be yourself. You get liberated.
Why don’t you want a summer house instead?
Oh, there’s no comparison! The fact that the world can change around you—it’s like a moving fortress of your own. Then having people join and having other boats tie up? The social part is unbeatable.
Do you change when you’re on Latitude?
I feel like I’m taking off from life. I have had some of my deepest conversations with my best friends on a boat. I have made some of my biggest decisions on a boat. I probably have had the best night’s sleep on a boat.
Kiel James Patrick (FRONT RIGHT) and his friends enjoy summer, retro-style.
This summer, it’s Jamestown. Last summer was Nantucket. There was Newport and Martha’s Vineyard, too. Kiel James Patrick and his buddies have been diagnosed with rental nomad syndrome, and they’re proud of it, thank you. They are also the best-dressed tenants any landlord will ever see. Patrick is the founder of KJP, a tony collection of apparel and accessories for men and women, which, conveniently, his housemates happen to love. Even more conveniently, they are open to having Kiel regularly style them. It all makes for some mighty fine photos, which have amassed nothing less than a cult following on Instagram.
How do you pick your rental houses each summer?
I always seek a house that offers as much personality and charm as the people who are coming to summer in it. Quirky history, century-old furnishings, eclectic décor, gorgeous waterfront views, and of course, a ghost or two is always a must.
How did your rental tribe start?
A few of my friends and I decided to pool some money together and rent a beautiful old house. We made a few rules. Everyone must dress in their nicest clothes for two days. Everyone must bring a unique recipe and be responsible for making a meal arranged so nicely that Martha Stewart would be proud. We talked. We told stories. We took pictures with our parents’ old cameras. At night, we’d toast by the campfire and sing. Inside, we played old records, just the way our grandparents enjoyed life.
What other cool activities do all of you like?
We play board games, sports, swim, and horse around. I love cooking. I love singing. I love dancing. I love connecting.
How long will the renting tribe continue?
This has brought us all such extraordinary happiness that we hope to keep sharing as we bring more and more friends along on our trips.
photography by eric levin; COURTESY OF THE CASHMAN FAMILY (PIGGYBACK, BAREBACK); courtesy of roy schoenberg; KIEL JAMES PATRICK (GARDEN, STAIRS)