When an Illinois state senator named Barack Obama stepped on the Vineyard that day in 2004, fresh from his well-received national debut at the Democratic National Convention, the island community not only embraced him — it wrapped him in a bear hug.
People streamed into Edgartown’s Old Whaling Church to see the rising political star, there to attend a forum on race relations. The wooden pews seat 800; 1,000 people showed up.
“The crowd just erupted when he walked out there with me,” said Obama’s former Harvard Law professor, Charles Ogletree, a Vineyard summer resident. “He felt, ‘Well, this is the place for me.’ ”
The Vineyard has indeed become Obama’s “place.” His nearly annual sojourns on the island have coincided with his growth as a politician, from state senator to US senator and presidential candidate to Oval Office occupant. Next month, Obama is scheduled to return again.
Already President Obama has spent more nights on Martha’s Vineyard than almost anywhere else besides the White House and nearby Camp David. His time there surpasses the amount of time he has been at his own home in Chicago, and is rivaled only by Hawaii, where he spends Christmas, according to data compiled by CBS News.
“He obviously fell in love with it,” Ogletree said.
For someone who was born in Hawaii, spent formative years in Indonesia, and went to colleges in California, New York, and Massachusetts before settling in Illinois, Obama appears particularly grounded in the sandy, scrubby island. The community Oak Bluffs is summer home to African-American intellectuals who helped nourish his early career. His family has returned to the same Atlantic Ocean beaches again and again.
Presidents have sought peace on the Vineyard’s shores since Ulysses S. Grant came to Oak Bluffs for three nights in 1874. But the island seems to bring something more personal, more comforting, to President Obama, who is on pace to at least tie Bill Clinton for most presidential Vineyard vacations.
The Vineyard, Obama said once, is “one of those magical places where people of all different walks of life come together. Where they take each other at face value.”
“I can wander around in shorts and not shave in the morning,” he added. “And no one talks about it.”
He made the comments at a fund-raiser in 2007. That was the last year he could pedal his bike around town without attracting much attention. Now, of course, the whole world would notice if his chin sported a vacation stubble.
Relaxation and routine
After his trip in 2004, Obama traveled there again in 2007. He skipped the campaign year of 2008, and then returned for three consecutive summers starting in his first year as president, in 2009.
Like President Clinton, Obama arrived in the White House without a family vacation home (the Bushes had one in Kennebunkport) or a ranch (Reagan had Rancho del Cielo).
Martha’s Vineyard served as a public stage for Clinton, a peripatetic social magnet during his vacations. He sailed and dined with the likes of James Taylor and Sylvester Stallone, and at night was known to pick up a saxophone at parties and jam with the band. He also held the occasional fund-raiser.
Obama’s vacation style is different, perhaps in keeping with his cooler, more insular personality. He spends time with a small, tight-knit group of loyalists and longtime friends. He is private and low key, engaging only occasionally with other politicians or celebrities on the island.
According to a Globe analysis of White House pool reports spanning his three previous Vineyard vacations, he spent a total of 583 hours (measuring both day and night) on the island — almost 80 percent of them cloistered at a rented estate.
“When he’s not working, he plays cards, hits the restaurants and ice cream shops, reads quite a bit and just enjoys time at the rental with his family and friends,” said Bill Burton, a former White House aide who was with Obama during his first presidential vacation, in 2009. “It really is a traditional family vacation, it just happens to have armored cars, Secret Service, and 100 members of the media in tow.”
Obama has not raised money on the island since he became president. He rarely holds any type of activities with donors — much to the dismay of some, who have wanted to throw fund-raisers for him. Occasionally, a contributor gets to join him for a round of golf. In 2010, he played basketball with Robert Wolf, then chief executive of UBS, and his sons.
The family’s adherence to routine is striking: the Obamas always buy fried shrimp from Nancy’s seafood restaurant in Oak Bluffs. Obama routinely takes his two daughters to Bunch of Grapes bookstore in Vineyard Haven.
They found a private beach they like near Oyster Pond, on the island’s southern shore. And they typically have taken a 6-mile bike ride in Manuel F. Correllus State Forest in West Tisbury.
Even a presidential motorcade is not immune from the island’s notorious traffic congestion: Obama spent about 17 hours on more than 66 trips driving around the island trying to get from point A to point B. And usually point B was a golf course. Obama has spent nearly 56 hours — or nearly 10 percent of his time — on the links.
His preferred course is Vineyard Golf Club, a private course that opened in 2002, and he almost always golfs with the White House trip director, Marvin Nicholson, and a longtime Chicago friend, Eric Whitaker. A fourth spot rotates to family friends or, in one instance, Mayor Michael Bloomberg of New York.
He also dines within a tight circle, which at times has included Governor Deval Patrick. A near-constant presence is Valerie Jarrett, a longtime friend and adviser who has vacationed on the Vineyard since she was a child and who hosted the Obamas on the trips before he became president. Of Obama’s nine trips out to eat, for example, Jarrett has been on all but one — and that was when the president took Mrs. Obama on a date.
Like most presidents, Obama invariably will be criticized for taking time off for a vacation — and, in this case, to a wealthy enclave in deep blue Massachusetts.
But Obama has taken far less time away from the White House than his predecessor, George W. Bush, who spent weeks at a time at his ranch in Crawford, Texas. Obama has taken 87 days off, compared with 399 days for Bush at a similar period in his presidency, according to CBS News’s Mark Knoller, who keeps detailed records of presidential travel.
A formative trip
When Obama travels on the island now, his motorcade can stretch 15 cars long. Secret Service scopes out each location beforehand, and the media is on hand to cover every handshake, book purchase, and golf outing. Each movement is highly scripted, containing little of the raw excitement of the church crowd he encountered in 2004.
But the 2004 visit remains memorable. At a cocktail reception hosted by Harvard professor Henry Louis “Skip” Gates Jr., Obama met Spike Lee, a movie director and Vineyard regular who holds a special place in the Obamas’ personal history.
“I owe you a lot,” Obama told Lee, recounting that his first date with Michelle was to see Lee’s movie “Do the Right Thing.” As they watched the film, Michelle allowed Barack to touch her knee.
“Good thing you didn’t choose ‘Driving Miss Daisy,’ ” Lee later recounted saying in response.
Obama returned to the island in 2007, when he attended a fund-raiser in preparation for the contentious Democratic presidential primary. He brought along his family, and they stayed for a week. One morning, he put on his White Sox cap, strolled into the local gym B-Strong, and put down about $45 for a weeklong pass.
He built up his heart rate on an exercise bike. He pumped weights. (“Not super heavy,” remembers co-owner Heather Neal, who still keeps the paperwork Obama filled out for his brief membership in a safe-deposit box.) Even as Michelle Obama hustled around the exercise stations with him, Obama went relatively unnoticed, Neal said.
Toward the end of the 2007 trip, the Obamas went to dinner at the Sweet Life Cafe, a restaurant in Oak Bluffs that serves contemporary French-American cuisine. It was one of the last times they would be able to dine alone, without an entourage, without a press corps, without a massive motorcade and Secret Service protection.
When they returned to the restaurant almost exactly two years later, as White House occupants, hundreds of people filled the streets. The Obamas shook hands with fellow diners as they exited from a two-hour meal. As they climbed into their black Chevy Suburban, they waved to the crowd as onlookers shouted “We love you” and “Thank you for everything.”