up-island (Martha's Vineyard) (in the off-season)

Chilmark, Menemsha, and Aquinnah for long walks and raiding farmstands for cheeses, spring veggies, flowers. Visit the Trustees of Reservations hiking trails to Menemsha Hills. Take the (friendly, amazing) bus to Oak Bluffs and Vineyard Haven for dreamy feasts of oysters and fried things by the water and two bar seats under the fairy lights at Sweet Life Cafe. No reservations needed... June is very much the off season. It's cloudy, cool, and breezy. It's perfect.