Nantucket

Nantucket is more uniform than the Vineyard — one town, one architectural language (gray shingle, white trim, brick sidewalks), one polished commercial center. The cobblestones downtown are real, not decorative. The outlying village clusters — Sconset to the east, Madaket to the west, Surfside and Cisco to the south — each have a single dominant beach and a smattering of houses; there's no second village center.

The beaches are the best on either island. Surfside is the south-shore Atlantic workhorse — big waves, a long stretch of sand. Jetties is the calm harbor-side family beach a short bike ride from downtown. Madaket is famous for its sunsets. Sconset has the cliff walk. There's no bad beach day if the weather cooperates.

Nantucket is small enough to cycle but spread out enough that you'll want a bike, an e-bike, or to coordinate with the Wave shuttle. The downtown dining and shopping scene is genuinely excellent and genuinely expensive — there is no cheap meal in Nantucket town in July. Plan the ferry, plan the lodging, and don't come for a single night.