Few people know their way around the Island links like local wunderkind Tony Grillo. As President Obama settles into a vacation in West Tisbury that is almost certain to include a few rounds, Mr. Grillo leaves for Seattle to compete in the U.S. Amateur Championship. Before leaving, though, he spoke with the Gazette at his home course, Farm Neck, about what the duffer-in-chief can expect on Vineyard fairways.

Today, just a week after placing third overall in the Massachusetts Public Links Championship, Mr. Grillo ships out for Seattle, his second appearance at the U.S. Amateur event. He says he has conquered the nerves that hindered his performance the first time around.

“I think my game is in a much better place than it was last year,” said Mr. Grillo, who says that his confidence is as high as it’s ever been.

In the fall he returns for his junior year at Harvard University where he hopes to capture an Ivy League Championship as captain of the golf team.

“Right now I’m just focused on that,” he says, “I’ve heard from my coach and from people on the team that these are the memories and the things you really care about when you look back at college.”

Mr. Grillo honed his considerable talents on Vineyard courses, courses whose surroundings he says President Obama would be well-advised to soak in for a truly rejuvenating vacation. Last year the president played Farm Neck, Mink Meadows and the Vineyard Golf Club.

— Allen Green

“This course is really mostly known for its beauty,” Mr. Grillo said of Farm Neck, where he works during the summer when he is not competing. “Almost half of the holes you can see the ocean, so when most people come that’s all they really talk about.

“It’s a course where you just have to hit it straight,” he said, advising the president against a long-ball strategy in favor of caution. “There’s a lot of holes where you don’t have to hit your driver.”

The course includes his favorite hole on the Island, No. 14, which famously terminates at the shore of Sengekontacket Pond for a view unmatched by other Island holes.

As far as other courses, Mr. Grillo enjoys playing the eighth at the intimate Edgartown Golf Club and the 15th at the Vineyard Golf Club, a deceivingly wide-open hole that requires players to navigate around a mischief-making pond.

The course de rigeur is the Vineyard Golf Club whose recent profile in the New York Times rehashed its status as the only organic golf club in the country. For Mr. Grillo, though, the greatest difference between that course and Farm Neck is its use of fescue, or field hay, which can make digging out of the rough after an errant drive especially difficult.

“It’s not an easy course,” he said, “and it’s kind of long from the back tees. Here at Farm Neck it’s the water and the hazards, but the Vineyard Golf Club penalizes you with the fescues.”

Certain holes around the world invite shudders in even the most experienced golfers: No. 17 at Sawgrass, the cliffs of doom at Pebble Beach. Does the Island have similar bogey-men?

“Here it’s the No. 12,” he says of Farm Neck. “It’s a tough dogleg right with a bunch of hazards and the wind’s normally in your face from right to left. It’s definitely a difficult hole to play well.”

As for other holes, Mr. Grillo counsels Mr. Obama to beware of Vineyard Golf Club’s No. 5, an equally tricky sharp dogleg right.

Much has been made of President Obama’s fondness for the game. At more than 30 rounds, he already has played more golf in his young presidency than George W. Bush, who famously announced in 2008 that he had given up the game in a show of support for troops serving overseas. Still, it is unlikely that any president could hope to match Dwight Eisenhower, who was rumored to have played over 800 rounds in his eight years as commander in chief.

But Mr. Obama is not the first putting POTUS on the Island. Bill Clinton has been known to haunt Farm Neck fairways and was spotted on the course as recently as last year.

In a ranking of presidential golf games, Golf Digest last year ranked President Clinton the seventh best, one ahead of Mr. Obama. “Can break 90,” the article said of Bubba’s game, “especially using his ‘Billigans’.” (Atop the list was John F. Kennedy, no stranger to the Vineyard himself.)

Before departing for Washington, Mr. Grillo offered some final words of encouragement to the president, who has described his own game as “terrible.”

“He should just have fun. Too many people get frustrated with the courses here because they’re a little too difficult, but if you just keep your eyes open, especially on this course, it’s tough to be disappointed.”