Along Main Street, which curves gracefully away from the harbor, there are yoga studios, art galleries, chic home furnishing shops, and all manner of restaurants. The harbor’s marina and yacht club are filled with fishing boats and pleasure craft of every description.
With parades on every holiday, it’s a welcoming place for people who simply want a relaxed, bayside alternative to the high-powered Hamptons a few miles away.
This in-town beach offers family-friendly bay swimming.
This crescent of white sand on Noyack Bay is a great place to pick up “jingle shells” and sea glass.
Don’t forget, the spectacular ocean beaches of the Hamptons are just 15 minutes away.
Dockside Bar & Grille
Nautical but not hokey, the Dockside Bar & Grille offers inventive seafood dishes such as lobster-avocado spring rolls. 26 Bay St., 631-725-7100 or docksidesagharbor.com.
LT Burger (left)
Stop in for outstanding burgers and serious shakes. 62 Main St., 631-899-4646 or ltburger.com.
Il Capuccino Ristorante
A local favorite for old-school Italian. 30 Madison St., 631-725-2747 or ilcapuccino.com.
Here, lobsters swim in a claw-foot bathtub, and patrons sit at a window counter with a bowl of one of the restaurant’s prize-winning chowders and watch the yachts and fishing vessels come and go. 1 Long Wharf, 631-725-7555 or dockhouseny.com.
Estia’s Little Kitchen
The weekend brunch is wildly popular, but don’t miss the more elegant dinner, when owner Colin Ambrose serves up roasted squash salad, striped bass, and café con leche flan. 1615 Bhampton Sag Harbor Turnpike, 631-725-1045 or estiaslittlekitchen.com.
Year-round, pick up The Sag Harbor Express for listings of live music, readings, and gallery openings. Anytime, take a self-guided walking tour of the historic district, with sites grand to charmingly funky. Pick up a brochure at the headquarters of the Sag Harbor Historical Society, sagharborhistoricalsociety.org.
Built in 1846, it remains at the epicenter of Sag Harbor life. It has eight spacious rooms, a four-bedroom apartment, and a 75-foot Trumpy motor yacht. Its French-American restaurant and classic, dimly-lit bar offer a renowned wine list. Tea, drinks, and light fare are served in the front parlor and on the front porch. Call for seasonal rates; 631/725-3535 or theamericanhotel.com.
This site links travelers with inexpensive homestay opportunities and often has appealing Sag Harbor listings. airbnb.com.