A fews days into our stay on Martha’s Vineyard, we took a drive “up island” to see a handful of different MVY towns. The Aquinnah Cliffs were such a site. If it weren’t for the classic New England-esque brick lighthouse sitting upon them, you could have told me I was in another country and I would have believed you.

Gay Head was Martha’s Vineyard’s first lighthouse, originally constructed in 1799. Its original purpose sounds like a dictionary example: to safely guide shipping traffic through the hazardous Vineyard Sound and surrounding clay cliffs… just look at them!

Oxford shirt, GAP [similar 1; 2] | Shorts, American Eagle [similar] | Belt, vintage | Bracelets, Kiel James Patrick [Vickers Bow + Brooks Brothers Wrap Bracelet] | Boat shoes, Sperry Top-Sider

Further down the road was Menemsha, where we browsed for antiques, wandered around an old fishing village, and ate hot dogs with a view of the cliffs. This area couldn’t have been more different from preppy Edgartown on the other side of the island, but it had so much irresistible character.