A tropical storm warning for the Massachusetts coast was cancelled Sunday morning, but the first family will likely bring a frenzy of a different kind to the beach.
Already whispers are swirling that Obama plans to pay a visit to ailing Sen. Ted Kennedy this week in Massachusetts.
Today, the U.S. Secret Service visited the Kennedy compound, ABC News learned -- though the White House said there are "no plans" for an Obama-Kennedy meeting.
Obama has also left behind a political storm in the nation's capital as he takes his week-long vacation.
Besides being an elder statesman for the Democratic Party, Kennedy is considered a champion of health care reform, and his lawmakers have felt his absence from Washington during the debate.
Today on "This Week", Sen. John McCain, R-Ariz., Obama's opponent in the 2008 presidential race, suggested Kennedy may have been able to smooth out some of the friction over health care.
"No person in that institution is indispensable, but Ted Kennedy comes as close to being indispensable as any individual I've ever known in the Senate because he had a unique way of sitting down with the parties at a table and making the right concessions, which really are the essence of successful negotiations," McCain said.
"So it's huge that he's absent, not only because of my personal affection for him, but because I think the health care reform might be in a very different place today."
"We've all heard the charge that reform will somehow bring about a government takeover of health care," Obama said. "I know that sounds scary to many folks -- it sounds scary to me, too. But here's the thing: It's not true."
No Public Events Scheduled During Vacation
Today, however, the first family left the White House and Washington behind, trading suits and skirts for flip flops and sunglasses.
The vacation marks the first full week off for President Obama since he took office in January and the first real family vacation for the Obama family.
First lady Michelle Obama and daughters Malia, 11, and Sasha, 8, have accompanied the president on jaunts overseas, but they have mostly kept their own schedule on those trips, taking in the sights and sounds of Europe while the president attended events and meetings.
Except for a few weekends at Camp David, and quick trips to Chicago and New York City, the president has stayed close to the White House, so this week's trip will be a true vacation, a break from policy and politics. That is if world events cooperate with his vacation plan.
Obama has no public events on his schedule for the week, and aides said he was not planning to meet with staff on health care. The White House will rely on surrogates to keep the message going while the president is out of the public eye.
In an interview earlier this summer, Obama defended his taking a vacation at a time when many Americans are out of work or struggling in the weakened economy.
"Do I think the American people think that because of those hardships I shouldn't spend some quality time with my daughters?" Obama said on July 21 when asked if he felt "guilty" taking the time off. "I don't think that's what the American people think about it."
Republican strategist Kevin Madden said presidents deserve some time off to recharge their batteries.
"Every American should consider it in the context of their own job. Consider how stressful it is and then multiply that by 100 and then ponder the idea of not getting to take a vacation," he said.
John Fortier, a research fellow at the American Enterprise Institute, said that presidents certainly deserve vacations, but like everything else in their lives, there are factors to consider.
"They have very demanding jobs and they are in the spotlight. But it's a political calculation as to where they go and what they should be seen doing," he said.
Madden noted that a presidential vacation can bring reward, but also risk.
"The main consideration here are the images: a presidential vacation can help the way it did for President Clinton when he visited the Grand Tetons, which are in a majestic national park setting," he said. "But you can also mistakenly convey a sense of detachment if the predominant image is one of a president on a gas-guzzling speedboat off the coast of Maine like President George H. W. Bush during the first Persian Gulf War."
What is the risk for Obama? Madden said he could look sheltered, vacationing on an expensive estate, and detached if he sits on a beach while the health care debate and other key issues continue to roll on without him.
First Family on the Farm
This is not Obama's first trip to the Vineyard. He has stayed there before for short vacations with friends, including senior advisor Valerie Jarrett, and has raised campaign cash on the island.
Despite considerable local buzz that the Obamas would stay in Oak Bluffs, a scenic enclave on the north coast of the island that is a popular vacation spot for African-Americans, the family will stay at Blue Heron Farm, a nearly 30-acre farm in Chilmark.
The farm, located on the southwestern side of the island, is secluded and will give the Obama family privacy that was not in great supply last year in Hawaii.
Last December, then president-elect Obama and his family vacationed in Hawaii and, without permission, a photographer was able to get within 150 feet and snap pictures of the Obamas sporting bathing suits and vacation wear.
Chilmark is more remote and secluded than other popular tourist spots on the Vineyard.
"Chilmark is the most reclusive, exclusive (town). That's where people really go to relax and unwind," said Dawn Bellante-Holand, general manager of Martha's Vineyard Online. "It's very laid back with a lot of the Hollywood types. It's where people really go to get away from it all."
The Blue Heron Farm is surrounded by other similar properties and the Obamas will have plenty of privacy if they choose to remain out of the public eye.
No other vacationers will be staying on the massive estate while the Obamas are there, due to security and the presidential entourage of staff and Secret Service.
Blue Heron Farm is owned by Mississippi developer William Van Devander, who was willing to take Obama's money for the vacation rental but donated to his opponent, Sen. John McCain, R-Ariz., in last year's presidential election.
In 1998, then-President Bill Clinton and his wife Hillary attended a party at the farm hosted in his honor by a former owner who died in a plane crash with his wife in 2003.
This isn't just any farm. The waterfront estate is located on the island's rural west end on West Tisbury Great Pond and was purchased by Devender for $20 million in 2005. The property features a five-bedroom, five-bath main house, guest quarters, swimming pool, barn and horse paddocks, apple orchard and boat house.
"It's the type of place that once you get there, it's not something you want to leave," said Vineyard real estate agent Tom Wallace, of Wallace and Company Sotheby's International Realty. "It's very tranquil, great place for a family vacation. The kids will absolutely have a ball as I'm sure Bo will also."
"It has very much of an old world feel to the property," he said.
Wallace would not disclose how much the Obamas are paying for the rental property.
Martha's Vineyard realtor Caroline Taylor, of Caroline Taylor Properties, estimates that the property would likely be rented for between $35,000 and $50,000.
White House press secretary Robert Gibbs said the Obamas will foot the bill for their vacation, as they have in the past including the trip he took as president-elect.
"I know that the Obamas are paying for their vacation, like they paid for a vacation last August in Hawaii and last December in Hawaii, as well," Gibbs said.
Remaining costs, for White House staff and Secret Service protection, will be handled as they are for other presidential travel, with taxpayer money.
All recent presidents have taken some time in August for a little rest and relaxation and their choice of destination can perhaps tell us something about their personality and their presidency.
George W. Bush, wanting to get away from the East Coast elite image that his father had, eschewed his family's scenic home in Kennebunkport, Maine and spent his down time at his ranch in Crawford, Texas, about two hours south of Dallas.
"Most Americans don't sit in Martha's Vineyard, swilling white wine," Bush said in 2002 when asked why he chose the hot and humid locale for his presidential vacation spot, deemed the "Western White House."
Bush fully embraced the dust and heat of central Texas, driving a pickup truck around his property, showing off the vast land to world leaders and providing the press with photo opportunities of him getting down and dirty clearing brush.
During his presidency, Bush spent a total 490 days at his beloved ranch, according to figures compiled by the unofficial White House statskeeper CBS News' Mark Knoller. In his first nine months in office, spent over 90 days at either his ranch or the presidential retreat at Camp David, Knoller notes.
Bill Clinton did not own a vacation home, so he and Hillary and their daughter Chelsea spent several summer vacations on Martha's Vineyard, staying with a wealthy Democratic donor. Clinton was ostensibly there to recharge his batteries but he was also a fixture on the social scene, bouncing from fundraisers to parties to local establishments.
George H.W. Bush holed up at the family compound in Maine and Ronald Reagan would spend a month at his ranch near Santa Barbara, Calif. Richard Nixon had a "Western White House" of his own in California and a "Florida White House" in Key Biscayne.
Presidential historian Fortier said presidential vacations have evolved with media and technology.
"In a way, the president's vacation has become something more of an issue today where the presidency is much more of a 24-hour job where the media follows the president around -- follows the president on vacation even," he said.
Obama heads to the Vineyard with the press in tow, but White House officials expect the president to remain largely out of sight with his family and some close friends.
Despite reports, there are no plans for the president to visit Sen. Ted Kennedy who is staying at his family's compound at Hyannis on Cape Cod, a White House official said.
ABC News' Kate Barrett, Alice Gomstyn and Sunlen Miller contributed to this report.