Dr. Aquilino Alamo takes a casual approach to athletic events, whether he’s running a marathon or planning his upcoming 45-mile race from Rockport to Boothbay Harbor.

“So far, I’ve been competing with people in marathons to get a good photo at the finish line,” he observes. “Now, I’m running against a boat.”

The “boat” is the topsail schooner Timberwind, captained by identical twins Joe and Bob Tassi of Camden. The event, called Jammers and Joggers, kicks off Boothbay Harbor’s Windjammer Days, a four-day festival celebrating its 50th anniversary this year. So the race distance is designed to approximate the number of Windjammer Days birthdays.

At 7:30 a.m. on June 25, the Timberwind will set sail from Rockport Harbor, destined for the Whale Park in Boothbay Harbor, some 45 nautical miles away.

Meanwhile, from near the statue of Andre the Seal in Rockport Marine Park, Alamo — with a torch in hand — will start his trek: three blocks down Pascal Avenue, left on West Street, across U.S. Route 1 and following Route 90 for about 10 miles to Waldoboro. Then it’s onto Route 1 through town and about 25 miles through Nobleboro and Newcastle before hanging a left to Route 27 in Edgecomb to the finish line at Whale Park.

Alamo estimates his run will take 7 to 7½ hours. “Unless I twist my ankle or get run over on the road,” he adds cheerfully. “I hope I can get a southerly wind.”

The Timberwind’s prospects are a bit more uncertain, he sounds slightly tickled to say, owing to potentially delaying or course-lengthening vagaries of wind and weather, especially fog.

Alamo — “Aqui,” as he is known, rhymes with Jackie — faces challenges. There are formidable hills on Route 90 in Warren, after the intersection in mid-Waldoboro and on Route 1 up to the Route 27 turnoff.

But Alamo, 45, at 5 feet 7 inches and 165 pounds, is a well-muscled runner and no stranger to long distance-races with scary course elevation profiles. Last month he did the Pineland Farms Festival 50K, running 5 hours, 15 minutes, 37 seconds. In 2011 he did the 50-miler at Pineland, in 10:38:38. He’s run a dozen marathons, most recently Gettysburg (4:15) in late April, and calls himself “a four-hour guy” with a 3:40 PR, who aspires to do a marathon in all 50 states.

More, he’s an Ironman triathlete who did Lake Placid last summer and is bound for the world championship ironman at Kailua-Kona in Hawaii in October, as a lottery entrant.

Given his busy career at Lincoln Medical Partners, and considering that he has four kids ages 6-16, one might fairly wonder how Aquilino manages to pack everything.

“Sleep is overrated,” he replies, citing ultramarathoner Dean Karnazes’ comment on spending a third of one’s life in bed.

Speaking of family, they (along with friends) make up the Joggers team that will help pace Aquilino. Oldest son Jude, 16, and 15-year-old twins Kyle and Karl — all of whom run high school track and two of whom have already done half marathons — will cover significant miles; 6-year-old Ariel, wife Chat, and 2-year-old Husky Jack will escort Aquilino to the finish.

A native of the Philippines, Aquilino did his residency in internal medicine in the Bronx, N.Y., then spent four years practicing in Machias, until 2002.

“That’s how I fell in love with Maine,” he says. “The outdoors. The small-town community. And then we came to Boothbay, which was the best move.”

Aquilino’s affection for the Boothbay region and desire to do something for it have spurred his Windjammer Days feat.

“I’m sure there are others who are faster, but maybe I’m the only one they know, or the only one crazy enough, or that they can afford. You feed me, I will run!” he said.

“But if by doing this I can inspire one person or family, it will be well worth the effort. I love this town, and I’ll do anything that helps it.”

And he will enjoy the experience, as he does the marathons he does not hurry to finish.

“Why kill myself?” he asks. “I run for fun. It doesn’t matter how fast you are, unless you’re a pro. You get the same medal, the same crappy food.

“Many years from now, I won’t remember my times. Ten yards from the finish, if I see people around me sprinting, I get out of the way and let them pass, so I can be sure to get a good photo. That way, the memory will stay clear.”

Whether Aquilino beats the Timberwind or not, his Windjammer Days race should yield a fine and memorable finish photo.

THE ED SHEPARD Memorial 5K, honoring Maine running legend and Maine Running Hall of Famer Ed Shepard, will be held at 9 a.m. on Saturday in Gorham.

Race director Mike Towle notes that the course, which starts on Morrill Avenue and finishes on South Street in front of the library, is flat.

The fee is a very fair $15, or $20 on race day. Awards go to the top three male and female finishers, plus age-group winners.

For more information and a race application, check out www.edshepardmemorial.com or contact Towle at 210-0318 or [email protected]

John Rolfe of Portland is a staff writer and a road runner. He can be reached at 791-6429 or at:

[email protected]