A boy plays in front Edgartown Light. The Clintons vacationed in what's arguably the Vineyard's toniest town in 1993, as houseguests of former US defence secretary Robert McNamaraPhotograph: Win McNamee/GettyA child plays at Ocean Park in Oak Bluffs. Ulysses S Grant stayed in one of the town's famed Victorian gingerbread cottages while serving as the 18th presidentPhotograph: Win McNamee/Getty'I can see Martha's Vineyard from my house!' The Soft As A Grape shop in Edgartown features a display of Barack Obama (and Sarah Palin) merchandisePhotograph: Win McNamee/GettyA girl fishes as the sun sets in Menemsha, a small village in Chilmark, where the Obamas will be staying. Close Clinton adviser Vernon Jordan has a summer house in Chilmark as wellPhotograph: Win McNamee/GettyA ferry leaves the town of Vineyard Haven for Woods Hole on Cape Cod. Most visitors to the island arrive by boat - the Obamas are taking Air Force OnePhotograph: Win McNamee/GettyA man carries his daughter on his shoulders while leaving Gay Head cliffs in Aquinnah. The town is a cultural centre for the Wampanoag native American tribePhotograph: Win McNamee/GettyMore Obama memorabilia for salePhotograph: Win McNamee/GettyA man fishes from the shores of Vineyard Haven. The town is the main port of entry to Martha's VineyardPhotograph: Win McNamee/GettyPeople eat behind Larson's Seafood in MenemshaPhotograph: Win McNamee/GettyThe entrance to Lucy Vincent Beach in Chilmark. The Obama family will be based in Chilmark during their holidayPhotograph: Win McNamee/GettyJohn Farrington of Edgartown shows off the 'Bobama' hat he designed to honour the Obama family dogPhotograph: Win McNamee/GettyDuring his presidential vacation on the Vineyard, Bill Clinton purchased gifts for former intern Monica Lewinsky from the Black Dog Tavern's gift shopPhotograph: Win McNamee/GettyVisitors take a stroll on the beach in Oak Bluffs. The town formerly known as Cottage City is now known for attracting a large number of African-American summer residentsPhotograph: Win McNamee/GettyA boy climbs on rocks after trying to catch baitfish in MenemshaPhotograph: Win McNamee/GettyThe sun rises over the town of Vineyard Haven Photograph: Win McNamee/Getty