Martha's Vineyard in July

Summer is peak season for good reason—July and August bring perfect beach weather and all attractions are open. But you'll pay premium prices and fight crowds everywhere. June is the sweet spot: warm enough for swimming, restaurants are open, but prices haven't hit their peak yet. September is gorgeous with fewer tourists and still-warm ocean temperatures, though some seasonal businesses start closing. October offers stunning fall foliage and lower accommodation rates, but many restaurants and shops shut down. Winter is beautiful but brutal—most tourist infrastructure closes, ferry schedules are reduced, and you'll need serious cold-weather gear. Spring is unpredictable with chilly temperatures and limited dining options, but you'll have the island mostly to yourself.