Experience what makes Shelter Island the un-Hamptons at Bob’s Fish Market (87 N. Ferry Road; 631-749-0830), where the waitstaff is blunt but helpful, the nautical décor is delightfully campy, and the daily seafood specials are all caught a few miles off the island. Ignore the lackluster bread and butter that begin the meal and order the daily special (market price). If you’re cooking for yourself during your stay, be sure to buy your fish at the adjacent market.
Taste the finest ingredients the East End has to offer at two-year-old 18 Bay, located in a charming 1893 farmhouse with wainscoted walls and a large porch. There’s a bar area where you can order à la carte, but the reason to come is the four-course, Italian-inspired tasting menu ($55), featuring ingredients from local purveyors like Sylvester Manor and Southold Fish Market, which includes four antipasti, handmade pasta, a choice of entrées, and dessert.
Order freshly harvested, locally raised seafood off the daily raw-bar menu at SALT, a casual marina-front restaurant in Little Neck Harbor, then try the Shelter Island clam chowder ($8) and blackened fish tacos (market price). After dinner you can move next door to the Shipwreck Bar for drinks and live music (Thursday to Sunday), but wine lovers should make a reservation for the tasting room to sample wines from North Fork–based Jamesport Vineyards.