From marina to mooring, one Portland boating family shows off their favorite summer spots.

I’ve watched the islands of casco bay come into focus as my plane swoops into the airport, vibrant spots of green floating blurrily in the rich turquoise-blue of the Atlantic. I’ve seen them from the shore as I run along the Eastern Promenade, wondering at the swells of land beyond the bay. I’ve seen the Calendar Islands—or, rather, I thought I’d seen the Calendar Islands—too many times to count. But there’s nothing like pulling up on an 18-foot-long wooden boat, cruising gently by the cliffs of one of the islands. It’s like putting on glasses for the first time. Rocks are sharper, the cut of each individual leaf as keen as a knife, and the gentle pulsation of a jellyfish seems disastrously, grotesquely close.

Scott Richards, owner of the beautiful old Lyman that has ferried me to this place, steers as his wife, Pam, sits shotgun. She’s shielded from the sea spray, but my hair is misted with water and salt. Their two adult children, Elle and Wes, lean up against the sides of the boat, pointing out features of the craggy rock as we glide past tiny Catnip Island and through the sheltered waters of Whitehead Passage. On the north corner of Cushing Island, a jutting rock creates the illusion of a face. “That’s why it’s called Whitehead,” explains Wes. “It’s an old man in a mountain.” Elle’s boyfriend Julian is here, too. He and Wes have just graduated from the University of New Hampshire, and they’re bursting with ideas about their summer. They talk about travel plans and road trip dreams. I listen to their conversation with one ear as I sip a can of beer and watch the waves bob slowly up and down.

An afternoon on a boat with a cooler filled with snacks and cold brews, pleasant company, and clear skies—does it sound like paradise? For me, it is. But for the Richards, this is a common occurrence. This is their summer.

Just an hour before, Scott ran me through the specs of his boat from the docks at the Saltwater Grille in South Portland (the Richards are friends with the owner, Mark Loring, who lets them use his marina as their point of departure). Pam untied knots while Scott readied the boat. While I marveled at the vintage craftsmanship, he expounded on the virtues of power boating. “I’ve learned that you’ve got to keep it simple, man. Pam and I can drive down to the marina and get out on the water in 20 minutes. We’ll cruise around and come back in time for dinner.” Although they also own a sailboat, his favorite watercrafts are runabouts from Lyman Boat Works, a 140-year-old company headquartered in Ohio (initially, Lyman sold cabinets but the company hit its stride building boats for the Cleveland Life Guard). “The average workingman could buy one of these back in the day,” he tells me. “It’s just a great boat, and I’m a wooden boat kinda guy.”

The boat in question is named Elle Carolyn, after their daughter. It’s had a little work recently, and Scott makes it clear that crafts like his require maintenance. “But if you give it a little TLC, it will last forever,” he says of his 54-year-old boat. He routinely reapplies varnish, and once every few years, he takes the time to strip the paint and fill any holes that have appeared in the raw wood. “It’s a ton of work, but it’s well worth it,” adds Pam.

Pam and Scott have been cruising around in Lyman craft since they were 18 years old. High school sweethearts, the couple grew up in Cape Elizabeth, graduated from Cape Elizabeth High School, got married on the shores of Sebago Lake, and eventually settled in South Portland. They’ve known each other for ages, and it shows. They have the kind of easy, laughing relationship that serves as a reminder of what love looks like. (As someone about to be married myself, I find their clear joy in each other heartening. I imagine it would be a warming force on even the coldest of feet.) “When we first started dating, we would go out in the boat all the time,” Scott recalls. Back then, they were driving Scott’s family boat, a 1958 mahogany Lyman that had been in the family since 1962.

“Lyman has been making boats since the 1870s and they’re all great,” says Scott. “They got their start making boats for the Coast Guard, and now it’s just a brand people know and love.” There are mechanics who only work on Lymans and groups dedicated to the wooden boat company, including the New England Lyman Group and the Lyman Boat Owners Association. “They’re very seaworthy, but they don’t have all the tilt and trim,” he says. “It’s almost like driving a Cadillac.” As he makes the comparison, he leans back and makes a motion as though he were slowly swiveling a steering wheel, arm straight, fist out. (If you can’t picture it, Scott’s gesture is the exact same move that became wildly popular in 2010 with the song “Teach Me How To Dougie.”) I think for a moment and ask him, “Don’t they call those big old cars ‘boats’?” Scott lights up and slaps my back. “Exactly! That’s where it came from. You’re not sitting there adjusting everything and going 90. No, you’re going 15 miles per hour and put-putting along.”

Although the boat and its captain have remained the same, there have been some changes to the summer routine. Their kids have been riding with them for over 20 years, but Elle and Wes don’t remember what Casco Bay was like decades ago. When Scott first started cruising these waters, there were far fewer boats docking in Portland. Pleasure cruisers were much less common, as were big, hulking power yachts and tourist-packed cruise ships. The area was dominated by fishing boats and locals—now, you see ships flying flags from other states, other countries. Back then, the waves were gentler. You wouldn’t see the kind of swells that tip an 18-footer to a 45-degree angle, nose pointed at the sky. This happens several times while I’m traveling with them. Scott finds these huge waves, created by the wake of a ferry or the passing of a 50-foot Sabre, rather annoying. I find it thrilling. These sudden plunges make my stomach swoop and my heart soar, like riding a bicycle down a steep hill or leaping from a high diving board into the blue pool below.

On the western side of Cow Island, there is a sandy beach, dotted with smooth dark stones and bordered by a formidable thicket of poison ivy. Scott navigates the water, steering around rocks as he pulls the boat close to shore. When the water is just ankle-deep, he drops anchor and we roll up our jeans and wade toward dry land. Elle and Wes unfold a picnic blanket and grab beverages. Elle stretches out, her long limbs browning in the sun. She begins running her fingers through the sand, picking out pieces of smooth sea glass, green and white and brown and blue. She creates a little pile on the blanket, a collection of commonplace cabochons, a tiny horde of humble treasures.

We spend a few hours here, sitting and talking as the sun begins its descent from noontime highs. The kids know this place well. They’ve been coming here for years. Last summer, they hiked across the island, visiting old military bunkers and peering inside the empty windows. A century ago, Cow Island was a military base, purchased by the U.S. Army for the purposes of defending Portland Harbor. In the early 1900s, over a hundred army men lived on this small piece of land, crowded into Fort Lyon. Now, the fort is a charmingly decrepit ruin, overgrown with weeds and decorated with graffiti. For the past 15 years, the island has been owned and maintained by Portland- based nonprofit Rippleffect. The western side of this “educational eco-campus” is available for public use, unlike some of the other islands that dot Casco Bay. Anyone can come here. Anyone can use this vibrant land. Strangely, not that many people do. Standing on the beach, looking out at the endless waters of the Atlantic, it’s hard to believe I’m just three miles from the rush of the city. We’re a fifteen-minute ride from the marina. A hop, skip, and a jump from my house on busy Forest Ave., where car horns and sirens lull me to sleep. But who would know that from the lush, green summer stillness? It’s a quiet that’s not quiet at all. Birds tweet, waves crash, and somewhere behind me, Pam teases Scott in a sweet voice. We could be anywhere, but of course, we’re in Maine. Where else can you live like this?

After our first trip, Scott and Pam invite me out again. This time, we’re headed to a raft-up with a few of their friends. For any readers unfamiliar with the process, a raft- up is when multiple boats come together, often on a single mooring. The owners throw ropes to their neighbors and tie their crafts loosely together, creating a floating community. A little town on the big water.

“Usually, whoever has the bathroom is in the middle,” Scott explains as we head out to meet his friends. First, we cruise to Great Diamond Island, where photographer Nicole Wolf is already out on the water with a few of her girlfriends. She hops from their boat to ours easily (a native Canadian, Nicole grew up on fishing boats). Pam calls to Rusty and Win, two brothers and longtime friends of the Richardses. After some discussion, they decide that the waters near Great Diamond are too crowded. It’s a Sunday afternoon, and it seems like the entire population of Cumberland County has taken to the bay.

We agree to motor over to Cow Island where the water is gentler and find a mooring there. A few minutes later, I’m climbing unsteadily from the decks of the Elle Carolyn onto the County Girl, named for Rusty’s wife, Susan Pillsbury. Another boat, the Seawitch, is roped up on the other side. Everyone shucks off their shoes and hops to the central boat. And so the raft-up begins.

Any uneasiness I might have felt as an interloper is dispelled quickly by the warmth of this group. There’s something about the combination of salt water and sun that feels just virtuous and stimulating enough to make up for our various vices— and to welcome outsiders in. Cigars are lit, wine is poured, and jokes turn bawdy as the day descends into evening. We snack on a semi-improvised spread, which despite its thrown-together nature is delicious— cheese from Aurora Provisions and homemade hummus and gourmet crackers with little dark flecks of beans dotting each piece. The wind pulls at my hair like an unruly child. But there aren’t any children here; it’s not a night for that.

As the air grows chilly, the conversation waxes and wanes, moving from the merits of teaching to the difficulty of planning a wedding. Eventually, it’s time to go home. It’s 9 p.m. and the sun is turning the waters of the harbor a glowing red. I feel the beginnings of a sunburn on my cheeks, but I don’t care. “This is the life, isn’t it?” calls Scott from the front of the boat. He doesn’t have to turn around to hear my answer. It’s lost in the roar of the engine and the slap of the waves, the endless music of a Maine summer.