The Obama Family's Favorite Vacation Spot Is No Secret

Barack and Michelle Obama are known for some pretty impressive vacation destinations. Since Barack grew up in Hawaii, the couple traveled there early in their romance so Michelle could meet Barack's grandparents. Over the years, Hawaii has been a frequent destination for the family and one of their preferred places to spend the Christmas season. Concurrent with Barack's presidency, the Obamas enjoyed numerous opportunities for international travel to countries like Ghana, Russia, and China.  When it comes to relaxing in the summer, however, Martha's Vineyard is the Obamas' top choice. 

Starting in 2004, the family made the first of numerous trips to the island. Years later, the Obamas vacationed at Martha's Vineyard once again. From 2009 to 2011, they rented Blue Heron Farm, a sizable estate that cost $50,000 per week. On its spacious grounds, property boasted amenities for working out and its own strip of beach. 

This price tag is small compared to the $11.75 million that the Obamas have spent for permanent accommodations on the island. In 2019, the Obamas purchased their Martha's Vineyard estate, and with seven bedrooms, the vast mansion has plenty of space for the family and additional guests. It also has its own pool, breathtaking views of the nearby ocean, and waterfront access. Now that they have a home of their own, it's a strong indicator that the Obamas have formed a lasting connection with the island.

When he chose Martha's Vineyard for a vacation destination, Barack Obama followed in the footsteps of past presidents. Way back in 1874, Ulysses S. Grant became the first chief executive to spend his summer break on the island. John F. Kennedy also visited the area before and during his presidency. In 1993, then-president Bill Clinton established his own family's annual tradition of vacationing there. Clinton's enthusiasm for Martha's Vineyard may have influenced the Obamas' fandom. For one thing, after all the Clinton visits, presidential security was familiar with the location. For another, when their visits are concurrent, Barack and Clinton enjoy hanging out together and playing golf. 

Residents on Martha's Vineyard are equally enthusiastic about their presidential guests. During Barack's presidency, groups welcomed the family when they arrived at the local airport. Since his presidency, Barack misses being unrecognizable, and while he'll never be able to recapture that anonymity, he can enjoy some privacy while on Martha's Vineyard. "[Residents] pride themselves on kind of ignoring celebrities and let them relax without being hassled or followed," Nancy Gardella, executive director of the Martha's Vineyard Chamber of Commerce, explained to The New York Times in 2009. Years later, during the summer of 2020, COVID-19 masking protocol helped Barack remain incognito as he biked around the island. "It felt pretty close to what I had imagined — that sense of freedom, that sense of being able to go wherever you wanted," Barack later reminisced to People.

Besides taking time for fun, Barack Obama and his family have spent time working during their visits to Martha's Vineyard. In 2011, the then-president traveled with an entourage of 150 personnel so he could craft economic policy during his break. Five years later, Sasha Obama served seafood at Nancy's Restaurant when the family made an excursion to Martha's Vineyard. Like her dad, Sasha had a contingent of secret service members observing her from afar while handled customers' orders. The Obama family had frequented the restaurant since 2009 and formed a bond with the business owner, making it a logical choice for Sasha's summer employment. 

Besides job opportunities, local businesses on the island frequently offer extra hospitality to the Obamas. For instance, Mad Martha's Ice Cream crafted "Barack My World," a bespoke flavor in honor of the then-president.  Since Barack's well known for his must-read book lists, a Martha's Vineyard bookstore pulled out all the stops so the voracious reader and his family could shop. In addition to providing a private shopping experience, they even gifted Barack a book not yet available for purchase. 

Barack's also done his part to promote tourism on the island. In 2021, he took full advantage of the spacious 29 acres of his Martha's Vineyard vacation home when he hosted his own milestone 60th birthday party. While the ongoing COVID-19 pandemic altered his original plans, Barack was still able to entertain 200 guests on his lawn.