First, whalers loved it, then writers. Now this close-knit community—only two and a half hours from Manhattan—attracts anyone in search of the perfect small-town escape
1 of 6Photographer: Annie Schlechter
It doesn’t take much to imagine the Long Island seaport of Sag Harbor as it was a century and a half ago, when whaling ships docked six deep at Long Warf. The architectural evidence of whaling’s heyday is still here, but there have been a few changes.
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.
2 of 6Photographer: Annie Schlechter
Sag Harbor’s Main Street and adjacent alleys are made for shopping. There’s stylish décor with a beach-house vibe at Beach Bungalow (left). Sage Street Antiques, in a white-painted mansion, is a must for collectors. Fashion hounds head for Donna Karan’s Urban Zen or rifle through pristine high-end apparel at Collette Designer Consignment. The Sag Harbor Cinema, an Art Deco structure with iconic neon signage, shows two or three art films and foreign films a day. Sag Harbor Variety is a rare surviving example of an old-fashioned five-and-dime.
3 of 6Photographer: Annie Schlechter
Havens Beach This in-town beach offers family-friendly bay swimming.
Foster Beach 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.
4 of 6Photographer: Annie Schlechter
Where to Eat and Drink
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 ordocksidesagharbor.com.
LT Burger (left)
Stop in for outstanding burgers and serious shakes. 62 Main St., 631-899-4646 orltburger.com.
Il Capuccino Ristorante
A local favorite for old-school Italian. 30 Madison St., 631-725-2747 orilcapuccino.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 ordockhouseny.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 orestiaslittlekitchen.com.
5 of 6Photographer: Annie Schlechter
What to Do
The calm waters surrounding Sag Harbor are ideal for crabbing, clamming, fishing, sailing, kayaking, and paddleboarding. Art and music festivals abound in season, and there’s an ambitious program of plays and musicals at Bay Street Theatre, a local institution.
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.
6 of 6Photographer: Annie Schlechter
Where to Stay
The American Hotel 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.
AirBnB.com This site links travelers with inexpensive homestay opportunities and often has appealing Sag Harbor listings. airbnb.com.