Pastel sailing paintings and wicker baskets are still being hawked like crazy in the Vineyard, but there’s been a big push to modernize the art and shopping scenes in recent years, especially in Oak Bluffs, where plans are under way to restore a church to house new galleries and live-work artists’ lofts. In the so-called SoHa (for South of the Harbor) district, the new Red Mannequin boutique (93 Dukes County Ave.; 508-693-2858) is stocked with French designer duds for kids and bright bead necklaces. Next door at Pik-Nik (99 Dukes County Ave.; 508-693-1366), you can browse vintage jewelry and art, and just a few doors down, the Dragonfly Gallery features works by locals like Renee Balter, known for her striking monoprint illustrations of island landmarks. The Alison Shaw Gallery is a great spot to pick through coffee-table books and fine-art prints, while the new hastings in the alley displays Vineyard stalwarts like Ron Hall, who shoots hauntingly vibrant landscape photos, and Rick Hoffman, who creates thickly layered abstract paintings.
Of course, it’s never all about shopping, not when there are such stunning beaches around. Head to the public strand at Aquinnah, off Moshup Trail, before the afternoon crowds arrive. After a few hours playing in Aquinnah’s clean, calm surf, dust the sand off with a hike along the mile-long base of Gay Head Cliffs, the island’s much-photographed, brilliantly colored formations, which lead directly up to picturesque Aquinnah Lighthouse. Skip the daytime tour and return on weekend nights, when the lighthouse stays open late for viewings of seriously beautiful sunsets.