Winnetu Oceanside Resort

Cozy, light-filled café and market blending artisanal goods, creative small plates, and standout wines perfect for an upscale picnic or quick gourmet fix.

This iconic Martha’s Vineyard bridge, famed from "Jaws," doubles as a lively fishing pier, beach spot, and daring jump-off point.

Nestled on Chappaquiddick Island, Wasque Beach offers a pristine 200-acre nature reserve perfect for lounging, BBQs, and serene beach exploration.

Hot Box serves up authentic Massachusetts vibes with iconic North Shore roast beef sandwiches and crispy South Shore bar pizzas in Somerville’s Bow Market.

Nestled in East Cambridge, Elmendorf is a charming baking supply shop and café that serves artisanal treats, fresh coffee, and an eclectic selection of baking gear, perfect for both pastry whizzes and casual snackers.

Tasting Counter serves a meticulously crafted multi-course feast in a sleek open kitchen, pairing seasonal local ingredients with thoughtful wine, sake, or beer selections.

Juicygreens in Jamaica Plain offers vibrant plant-based arepas, smoothies, and baked goods in a cozy setting, perfect for a health-conscious bite.

Brassica Kitchen & Café serves creative, globally inspired small plates, legendary fried chicken, and inventive brunches in a cozy, buzzing JP spot.

Nestled in a charming 19th-century house near Harvard, this cozy B&B offers friendly vibes, tasty breakfasts, and a homelike atmosphere.

Legal Harborside is a sprawling, three-level seafood spot in Boston's Seaport with stellar harbor views, offering fresh lobster, sushi, steaks, and cocktails.