The Obama family also joins the historic tradition of well-to-do African Americans who've chosen Martha's Vineyard as a summer retreat for more than 200 years.
When news of the family's August vacation was first published this spring, several reports speculated the Obamas would stay in Oak Bluffs, the center of the historic African American community on Martha's Vineyard and the town where several Obama family friends vacation.
But the Obama family decided to forego an Oak Bluffs vacation and instead stay on the other side of Martha's Vineyard at an estate in Chilmark.
Vineyard resident Elaine Crawley Weintraub, director of the Martha's Vineyard African American Heritage Trail, was not surprised by the president's choice.
She noted Oak Bluffs has a strong tradition of African Americans who've vacationed on Martha's Vineyard with their families for decades, but added, "Obama doesn't really belong to that generation."
Chilmark also offers the president more options for privacy and seclusion.
"There are no houses in Oak Bluffs where you can have the security needed for a president," Weintraub said.
Although staying in Chilmark, Obama golfed Monday at the Farm Neck Golf Club in Oak Bluffs.
Many Oak Bluffs residents had prepped their town in advance, hoping the president would stop by.
Lawns were posted with welcome signs and local stores were selling everything from Obama family mugs and t-shirts to more unique items like Obamaritas, special orange-flavored margaritas now on the menu at Sharky's Cantina in Oak Bluffs.
Martha's Vineyard: Historic Haven for African Americans
Oak Bluffs also boasts sites of importance to Martha's Vineyard's African American history.
For generations, the Oak Bluffs community has had the threads of color and class holding a close-knit community of African American families together.
Famous African American homeowners in Oak Bluffs over the past century include former Harlem Congressman Adam Clayton Powell, Jr., Harlem Renaissance writer Dorothy West, and former U.S. Senator Dr. Edward Brooke. Each of their homes are now preserved as historical sites that the Obamas may visit while on Martha's Vineyard.
"I see President Barack Obama and the first lady continuing a tradition that has been part of African American life for those who want to vacation in the summer," said Bob Hayden, a historian and retired teacher who has been going to Oak Bluffs every summer since 1961.
The Obamas can also go to the Oak Bluffs Beach, popularly known as the Inkwell. The Inkwell is a community pillar in Oak Bluffs. It was the setting for the 1994 namesake movie "The Inkwell," and hosts the Black Polar Bears, a group of friends and neighbors who gather each morning at 7:30 a.m. for a swim.
The Polar Bears "come to network early in the day, relax and to wake up in the cool breeze of the Nantucket sound," Hayden said.
The Polar Bears trace their gatherings back to the 1940s.
First daughters Sasha and Malia may want to stop by the Flying Horses, the nation's oldest operating platform carousel, or the Waters of the World, a new aquarium just opened in Oak Bluffs.
While in Oak Bluffs, the Obamas might visit their longtime family friend Charles Ogletree, a professor at Harvard Law School. Filmmaker Spike Lee also has a home in the town.
Closer to the Obama family's vacation rental in Chilmark, other prominent African Americans also have summer homes, including longtime Bill Clinton adviser Vernon Jordan and Harvard Professor Henry Louis Gates Jr.
Chicago friend and White House senior adviser Valerie Jarrett is also taking time away from work on Martha's Vineyard this month.
Family and Tradition on Martha's Vineyard
During times in the nation's history when Jim Crow segregated public schools, restaurants and transportation, Oak Bluffs remained an integrated community and retreat for many families from discrimination.
"African American families and individuals started coming here right after the Civil War," Hayden said. "They came primarily as individuals, solo men and women because there were tremendous job opportunities here. Some decided to stay over into the fall and others came early in the spring."
As those working-class individuals and families eventually became middle-class, African Americans began purchasing homes in Oak Bluffs from what was formerly a Methodist Revival Camp.
Jill Nelson, author of "Finding Martha's Vineyard: African Americans at Home on an Island" traveled to Martha's Vineyard with her family for the summer months for 50 years.
"Certainly the Vineyard is not a racial utopia, but it was and is better than most places," Nelson wrote in her book.
"On the Vineyard we were insulated from many of the racial assumptions and expectations, most of them negative, that at the least intruded upon and at worst defined many of our lives off-island."
For Nelson, Oak Bluffs was about family and traditions -- traditions that continue for families like Bob Hayden's. This summer, the Haydens will enjoy a vacation that includes three generations of their family tree.
"My three adult children came with me in the '60s and '70s and now as adults in their thirties and forties, they come every summer, now with their children, my grandchildren," he said.