GO THERE: Channel summers past in the quaint sailing outpost of Roche Harbor on San Juan Island, part of the charming San Juan Island chain near the Canadian border. Start by booking a house with rental-by-owner outfit VRBO. We adore the clapboard cottages of the Bellevue Farm estate, where you can spend your days lolling about the waterfront digging for oysters. If you’re after turndown service, the Hotel de Haro has rooms overlooking the marina. For dinner, grab a seat on the deck at Madrona Bar & Grill, perched over the bay, and order the huckleberry baby back ribs. —Elizabeth Doyle
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