It's evolved into one of the riskiest pursuits in modern politics: vacation.
set out for what's intended to be a minimalist Hawaiian holiday: eight days away from television cameras and with family and friends.
If he pulls it off, he'll be one of the luckier ones.
John F. Kerry's leisure quests in 2004 - snowboarding in Idaho, windsurfing on the Nantucket Sound - reinforced the elitist label Republicans placed on him.
Former President Bill Clinton became known as the guy whose aides polled potential trip destinations. President Bush was mocked for vacationing too often, while his father was criticized for retreating to his family compound in Kennebunkport, Maine during the 1992 election.
Vacations "are fraught with peril," said Susan Estrich, manager of the 1988 presidential campaign of former Massachusetts Gov. Michael Dukakis, who faced his own spate of bad press for taking off much of August. "That's why [John] McCain will go hide at his ranch for a few days and be done with it. Poor Obama, he doesn't have a ranch."
Unlike McCain or the Bushes, Obama has no family compound to shield him from the cameras. He learned this lesson before he even formally announced his candidacy, when he was captured shirtless on a Hawaiian beach in December 2006 by paparazzi. The photos appeared in People magazine, embarrassing Obama when reporters showed it to him at the Capitol.
He might find himself similarly exposed this time as he settles into an island rental.
"There will be people with very long lenses," said Robert Thompson, founder of the Bleier Center for Television and Popular Culture at Syracuse University. "Getting him in a swimming suit will be one of the big gets."
He is staying at a secluded beach rental, obscured from the road by a long driveway and trees, about an hour's drive from Honolulu. The families of two close Chicago friends, hospital executive Eric Whitaker and parking lot magnate Martin Nesbitt, joined the Obama family at the house. One senior campaign aide, Robert Gibbs, also made the trip.
TV producers and crews, along with a handful of print reporters, have flown to the island to track his movements as part of the media's usual "protective pool" coverage. But other than a fundraiser Tuesday at a Honolulu hotel, campaign aides said they expect Obama to make little news.
"One of the great mistakes campaigns make is that we just burn out the candidates," said Tad Devine, a former Kerry strategist. "Particularly after he won the nomination, Kerry needed to take some time. That is when he made a couple of mistakes in public events that he would not have made if he had taken off a few weeks."
Obama acknowledged Thursday that his absence might be welcomed, given a Pew Research Center poll that found 48 percent of voters reported hearing "too much" about him.
"We are going to correct that this week, hopefully with your help," Obama told reporters.
Yet after he arrived here Friday, he completed a round of local TV interviews before heading to Keehi Lagoon Beach Park for a public "welcoming" event. Obama has campaigned in every state except Alaska, Arkansas and Hawaii, so this offered the chance to check the islands off his list.
"I want you to know that we aren't here to politick," Obama told about 4,000 people who gathered at the park. "The main purpose of me being here right now, before I head off and see my grandma, is to say thank you to all of you because all of you worked so hard to put me in a position where I may have the honor of serving as your president of the United States."
If Obama has no intention of politicking, his Republican rivals signaled Friday that they would in his absence. McCain's campaign reeased three attack ads, and the Republican National Committee needled Obama with "Barack Obama's Hawaii Trade Guide," a roadmap to key sites on the island, including the prep school he attended on scholarship and one local filling station with especially expensive gasoline.
In the age of 24-hour cable coverage, YouTube and camera phones, there is an ever-expanding playbook for holiday excursions, experts say.
First, politicians should give some consideration to how their vacation spot will look to voters.
After Kerry retreated to Nantucket during the Republican convention, footage of him windsurfing there later surfaced in an attack ad deeming him the candidate who votes "whichever way the wind blows."
"I remember any number of people at the time saying that should have gone to [his wife] Teresa's farm" in Pennsylvania, Estrich said. "You don't go to Nantucket until you've won."
Clinton took location hunting to the extreme when advisers suggested that he go fishing and hiking in Wyoming instead of taking his usual trip to Martha's Vineyard in 1995.
"There was a message that we thought would be conveyed by Martha's Vineyard that may not be positive," said Douglas Schoen, a pollster for Clinton's reelection campaign.
Schoen thinks Obama's Hawaiian vacation may convey a similar message to voters.
"For somebody who has been called 'elitist,' going to Hawaii is not exactly going against type," Schoen said. "I would rather have him going to national parks."
Obama has ties to the islands, having spent much of his childhood in Honolulu, where he graduated high school. When talking about his vacation this week, Obama often stressed the importance of visiting his grandmother, a Honolulu resident who played a big role in raising him. His grandfather, a World War II veteran, is buried at Punchbowl National Cemetery in Honolulu.
Hawaii is a home to Obama, said Stephen Hess, a presidential historian with the Brookings Institution. "You shouldn't hold it against him because it is a nice place to have a vacation. Anybody who picks on him for going to Hawaii is really looking for something to pick on."
The second half of the political equation is the way activities play visually.
"Obama needs to keep his shirt on," Estrich said. "Sand castles are OK. No dancing on the beach with your wife," a reference to Bill and Hillary Clinton's bathing suit duet in the Virgin Islands at the height of the Monica Lewinsky scandal.
Obama and his aides have disclosed little about how the senator plans to spend the week, although he offered some clues during his speech Friday.
He said he might stop by Zippy's, an Hawaiian chain restaurant known for its chili, or the Rainbow Drive-In for a Hawaiian "plate lunch," a mix of rice, macaroni salad and meat.
"I am going to go get some shave ice," he said. "I am going to go bodysurfing at an undisclosed location. I am going to see my Tutu, my grandma. And I am going to watch my girls play on the beach, and maybe once in awhile I will go in the water. But mostly I am going to sit there and watch them."
Experts, though, warned that Obama should take care with his outdoor activities, lest they be replayed on "The Daily Show with Jon Stewart" or used in an attack ad.
"Whenever he is out, he needs to make the assumption that the mic is on or it is somewhere near him, and cameras are photographing him with a telephoto lens," Thompson said. "This will not be a vacation. It will be a performance."
By Carrie Budoff Brown