Some Obama friends, including White House adviser Valerie Jarrett and Chicago physician Eric Whitaker, planned to accompany the family. The president has no official events scheduled in the week ahead. Don't be surprised if he finds time to tee it up on the golf course.
Then there are the likely trips for ice cream and salt water taffy, possibly a bike ride and plenty of quiet time at a secluded 28-acre private estate that rents for $35,000 a week. The Obamas are paying for their share of the vacation home; taxpayers are picking up the tab for security and White House staff, which is customary for all presidents.
Ahead of the trip, Obama and his aides asked for privacy for his daughters, 8-year-old Sasha and 11-year-old Malia.
"It is our strong hope and desire that you all, during this family vacation, will respect the privacy of Sasha and Malia Obama. This is a strong request by the first family," press secretary Robert Gibbs told reporters, conveying a direct appeal from the Oval Office.
There's talk that Obama may visit ailing Sen. Edward Kennedy at his vacation home in Hyannis Port on Cape Cod. A visit with Kennedy, who has brain cancer, could provide a rallying point for Democrats as Obama seeks to achieve one of Kennedy's career goals: overhauling the nation's health insurance system to provide near-universal coverage.
Vendors on Martha's Vineyard are selling T-shirts with the first family's pictures and even promoting Bo, the first dog who will join the Obamas. There are cupcakes and ice creams named for the Obamas and cardboard cutouts of the president in storefront windows.
The Vineyard is just 23 miles long with a year-round population of about 15,000. Any motorcade is certain to draw attention on an island already crowded with summer visitors.
The playground for the rich was a vacation spot for President Bill Clinton and President Ulysses S. Grant. Obama has visited twice before. More typically he has vacationed in Hawaii, where he was born and spent time as a child.
Bill and Hillary Rodham Clinton were island regulars through the highs and lows of Clinton's presidency. On their first presidential vacation there in 1993, they were photographed happily sailing, golfing and exploring the island's restaurants and scenery together.
Five years later, it was a different story. The Clintons headed for the island just hours after the president publicly confessed to an inappropriate relationship with intern Monica Lewinsky.