Moving into a bigger space has serious upsides, from finally separating your living room and dining area, to being able to invite over your friends, who unfortunately turn them both into bathrooms. Moving into a larger residence and not letting any degenerate pals soil it: 18 Bay.
Formerly an intimate, 16-seat boite in Bayville, the chef-owners behind 18 can accommodate almost four times as many diners in their new, 150yr-old Shelter Island home, which sports old-timey touches like an antique wood-burning stove, and a covered porch; they're also now closer to the produce they use, likely important to people who claim to be "ambassadors to the bastard vegetables" (clearly their mothers had legumes, and knew how to use 'em). The Italianate, seasonal, four-course tasting menu rotates nightly, and starts with a choice of four antipasti, which could include fried local squid w/ cherry peppers & chili mint sauce, or fluke crudo w/ Cape Gooseberry vinaigrette, which, in spite of all its bum pinching, technically isn't saucy. Things progress with a single handmade pasta (lamb tortelloni? hen-of-the-woods agnolotti w/ truffle butter?), before moving to your choice of the fish or meat entree of the night, e.g., line-caught striped bass w/ braised cranberry beans, and NY strip w/ peppers and Yu Choy, also known as edible rape, so...there's that.
The boutique vino selection constantly shifts as well, with Italian bottles sharing space with locals like a Gruner Veltliner from North Fork's One Woman, which'll be more than ever spend the night at your new spacious pad if you keep inviting your trigger-happy friends over.