1. Aquinnah, MA
Located on the western edge of Martha’s Vineyard, the quaint town of Aquinnah (previously known as Gay Head) stands out for its mile-long cliffs made of colorful clay. It’s also here where you’ll find the historic Gay Head Lighthouse, open seasonally from Memorial Day to Labor Day and offers some of the region’s most striking coastal views thanks to its clifftop locale. Lobsterville Beach offers a secluded feel and calm waters, while Moshup Beach (AKA Aquinnah Public Beach) is famous for its smooth stretches of sand and large waves; however, keep in mind that some sections of this beach are clothing-optional. Meanwhile, culture and history buffs will appreciate visiting the Aquinnah Cultural Center, where you’ll find educational exhibits highlighting the Wampanoag tribe and culture. Finally, cap off your sun- and fun-filled day with dinner at the seasonally open Outermost Inn, which offers a delicious raw bar plus flavorful fare ranging from fried green tomatoes to duck confit.