A Friday ferry from Greenport deposits you at Sunset Beach, where the light hits the bay in that particular gold that makes you understand why people stay. Three nights in a cottage-style room overlooking Crescent Beach—linen curtains, a claw-foot tub, the sound of water at all hours. Dinners at Vine Street Cafe, where the crudo arrives on slate and the wine list reads like a love letter to natural producers; mornings of bocce on the sand with rosé in hand, the kind of slow ritual that feels like the opposite of a countdown. A private sailboat charter on the final afternoon—the North Fork vineyards visible across the water, the sun dropping behind Robins Island, everyone quiet, everyone exactly where they need to be.
Five quick questions, then we build the full itinerary — lodging, daily schedule, dining, bars, the group-chat message — and drop you into a Trip Room you can share with the crew.