The list keeps growing. The picks stay opinionated.
7 picks from Boston.
Direct flight to a city where every neighborhood feels like a different decade. Alfama's tile and trams, Bairro Alto's night energy, Belém's custard tarts at the source. Lisbon works because it never tried to become Barcelona.
Mass MoCA in the morning before the busses arrive, a long lunch at Allium, James Turrell's sky-space at sunset. Three nights in the Berkshires is the culture weekend that doesn't make you choose between the museum and the hike — you do both, then eat dinner somewhere that sources from farms you drove past.
Gilded Age mansions on a cliff walk, oysters that cost what they should, and a harbor town that earned its reputation before Instagram. Two nights gets you past the Breakers selfie line and into the Newport that sailors and old money still recognize.
Two hours up the coast, you walk off the bus into a port town that got serious about food before anyone else was paying attention. Lobster rolls that cost what they should, a small hotel overlooking Casco Bay, and a Friday night that ends at Eventide around 9pm because that's when the oyster counter gets good.
Two hours and a ferry ride to the island that empties out after Labor Day and becomes itself again. Grey shingles, cobblestone Main Street, a harbor that still smells like a harbor. The Wauwinet is open through October and knows what it's doing.
Two hours north of Boston to a Vermont town that knows what it's doing in October and May better than it does in February. The Trapp Family Lodge sits on 2,500 acres of meadow and forest — yes, that Trapp Family — with trails that empty by 4pm and a dining room where dinner still means three courses.
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Two hours up I-95 to the Maine coast city that figured out how to be a food town without turning into a food scene. Lobster rolls that locals actually eat, a walkable peninsula, and a harbor that still works for a living. Stay at the Press Hotel in the old newspaper building and eat like you mean it.
