"It's not the best time to walk away," says Steven Schier, professor of political science at Carleton College in Minnesota. "It's better to take vacations in a quiet August. This is not a quiet August."
"Martha's Vineyard doesn't need any more local civic pride. It's overflowing with it," says presidential historian Douglas Brinkley. "When the economy's this bad, presidents should be vacationing in the states that need it the most. We've got some beautiful islands where I'm from in Ohio."
Fried clams and 'chowdah'
Presidents as far back as Ulysses Grant have come here to vacation, or fish for stripers and blues off the picturesque coast.
The most recent was Clinton, who adopted the Vineyard as his preferred summer spot in seven of his eight White House years.
Obama has come here several times. One of his top advisers, Valerie Jarrett, is a regular on the island. For generations, Oak Bluffs has been a vacation spot for thousands of affluent African Americans. Obama's friends include Vineyard regulars and Harvard professors Charles Ogletree and Henry Gates, who was arrested at his home in July after a confrontation with a white police officer, then later shared a beer with Obama and the officer at the White House.
The Vineyard also is friendly territory for Obama, who won nearly 75% of the vote here in 2008. In Chilmark, one of six island towns, he got 590 votes to 123 for John McCain.
For this vacation, Obama has chosen tranquility. Blue Heron Farm, owned by William and Mollie Van Devender of Jackson, Miss., is a 28-acre estate that rents for $35,000 or more a week with a pool, tennis court, golf hole and bocce ball court. Obama is paying his family's share of the cost, the White House says.
William Van Devender is an investor, real estate developer and venture capitalist focused on timber lands and wireless communications.
The Van Devenders are active Republicans who contributed $2,300 first to primary contender Fred Thompson and then to nominee McCain last year. They purchased the farm for $20.35 million in 2005.
Obama's temporary home is near the middle of the 23-mile Vineyard, away from its bustling east end and bucolic west end.
It's a half-mile from Alley's General Store in West Tisbury, which celebrated its 150th anniversary last year — and where the only sign of the presidential visit is a box of Obama trading cards on the counter and a group of curious onlookers on the front porch.
In Chilmark (year-round population: 843), where long driveways hide many properties, the median value of a home in 2007 was more than $1.5 million. Local real estate ads advertise 6.9 acres on Squibnocket Pond for $9.75 million and a building lot with beach access for $4.2 million.
Edgartown, Oak Bluffs and Vineyard Haven each has its own golf course. Menemsha's charter fishing captains all but guarantee ample quantities of striped bass and bluefish. Chilmark has spectacular beaches and ponds. Aquinnah has a Native American tribe and red cliffs.
It's anyone's guess where and when the Obamas will appear from their hideaway, conspicuously marked by about a dozen "No Parking" signs that state police placed on both sides of South Road. Even The Bite, a 14-by-14-foot clam shack on the dead-end Basin Road that leads to Menemsha Beach's famous sunsets, was alerted by the Secret Service for a possible Obama visit.