Obama and his family landed at a Coast Guard station on Cape Cod before heading to their final destination - Martha's Vineyard.
Before leaving the White House, he told reporters that he was ready "to not have a suit on for a while."
Obama is breaking up his vacation with a two-day return to Washington midway through the trip.
The president typically keeps a low-profile on his annual summer vacations. But he will headline a Democratic fundraiser on the island Monday night.
The president and his family are staying in a rented vacation house in the town of Chilmark.