If you’re boating in—
Find the farmers market just a stone’s throw from the Sag Harbor Municipal Dock (sagharborny.gov) on the grounds of the Sag Harbor Yacht Club (sagharboryc.com). In addition to seasonal produce, you’ll be offered samples of local edibles worthy of provisioning the finest galley, such as Amagansett Sea Salt (amagansettseasalt.com), Open Minded Organics fresh herbs (openmindedorganics.com), and Sagaponacka Vodka (sagaponackfarmdistillery.com). Plus, everything you could need to throw a fine picnic, like Mecox Bay Dairy cheeses (mecoxbaydairy.com), Blue Duck Bakery breads (blueduckbakerycafe.com) and Wölffer Estate Vineyard wines (wolffer.com), including their famous rosé, chilled.
Locate anything your boating adventures require next door at Sag Harbor Yacht Yard & Ship Store (725-3838) and Tight Lines Bait & Tackle (725-0740).
Across the street you’ll find phone chargers and much more at Geekhampton, the Hamptons’ only Apple Premier Partner (geekhampton.com).
If you’re motoring in —
You’re likely heading in on the Sag Harbor-Bridgehampton Turnpike which becomes Main Street. From this direction you’ll be tempted to join the masses for breakfast at Estia’s Little Kitchen (estias.com). It’s popular for good reason, but consider waiting until later for a low-key lunch or dinner, if American/Mexican appeals.
Just past the Mashashimuet Park tennis courts (mashashimuetpark.org; relax, everyone calls it “Mash” Park), locals grab a real-deal egg sandwich to start their days at the Cove Deli (283 Main Street, 631-725-0216). Their most popular take on this Long Island classic is bacon, egg and cheese—on a kaiser roll, of course.
Across the street from “the Cove” is Sag Harbor’s nearly 40-year-old independent, Canio’s Books (canios.wordpress.com). Grab the latest novel or a classic by a local author like John Steinbeck, E.L. Doctorow or James Fenimore Cooper.
Or is it time to linger over brunch at Wölffer Kitchen (wolfferkitchen.com), Baron’s Cove (caperesorts.com) or Il Capuccino Ristorante (ilcaps.com) (beware bottomless Bloody Marys)? Or maybe grab a dozen different brioche-style donuts from Grindstone Coffee & Donuts (grindstonedonuts.com). Sag Harbor is not known for its health foods—except those found at Provisions Café (provisionsnaturalfoods.com) and the sushi at Sen (senrestaurant.com). Now that you’re fueled, finding ways to spend the rest of the best day in Sag Harbor is easy.
Rent a paddleboard or kayak from Flying Point (flyingpointsurf.com) and walk it to the bay—or rent a bike from Sag Harbor Cycle Company (sagharborcycle.com) to visit nearby Long Beach. A walk, or run, up and down its length is over two miles.
Check the local newspaper The Sag Harbor Express (sagharbroexpress.com)—or tune in to our famous time capsule of a radio station, WLNG at 92.1 FM (wlng.com)—to find out what local venues are up to. Many of our most architecturally and culturally significant sites offer events such as concerts, art exhibitions and tours. Local draws include the Annie Cooper Boyd House (sagharborhistorical.com), Bay Street Theater (baystreet.org), Eastville Heritage House (eastvillehistorical.org), John Jermain Memorial Library (johnjermain.org), Old Whalers’ Church (oldwhalerschurch.org), the Sag Harbor Whaling & Historical Museum (sagharborwhalingmuseum.org) and Temple Adas Israel (templeadasisrael.org).
Sag Harbor boasts one of the East End’s top antique stores in Black Swan Antiques, its many one-of-a-kind finds like old maps and signage, maritime tools and vintage sports equipment are located adjacent to top showroom Grenning Gallery (grenninggallery.com). Check out some of the other galleries on Main Street like Keyes Art (juliekeyesart.com) and Tulla Booth Gallery Fine Art Photography (tullaboothgallery.com).
Don’t miss Washington Street for some of the best period interior pieces at Le Lampade (lelampade.com) and Ruby Beets (rubybeets.com). And, if you need a little sartorial infusion to meet Sag Harbor’s casual dress code, T-shirts and sweatpants are the top sellers at Henry Lehr Men (27 Washington Street, 631-808-3635).
If you want to make a splash in this village’s dining scene, try a waterside table at Le Bilboquet (631-808-3767) or in view of the water at Dopo La Spaggia (dopolaspiaggia.com), on the porch of the American Hotel (theamericanhotel.com), at Lulu Kitchen & Bar (lulusagharbor.com) facing the wood-fired kitchen or looking down on the water from the Beacon (beaconsagharbor.com). The local American Legion Post provides some top seats at The Dockside (docksidesagharbor.com) where outdoor seating faces the water and, inside, you can check out cool art films screened across canvas walls.
If you want to dine in the lap of luxury while trying out tables and chairs that you might purchase for your own home, check out Urban Zen/Tutto il Giorno—mother and daughter team Donna Karan and Gabby Karan Felice have sandwiched a tremendous amount of design and deliciousness into this former gas station. You’ll often find a DJ rocking the house on Saturday nights. (urbanzen.com; tuttoilgiorno.com)
You picked out a cigar at the American Hotel, right? Top spots for late night bites and bevs are Back Page Patio Café (page63main.com) and the nearby Murf’s Backstreet Tavern at 64 Division Street. At press time, Murf’s, a classic dive bar, was about to open under new management that promises to keep it just as small and haunted as ever. Be very aware that there’s a game of darts being played just inside Murf’s front door; enter cautiously and you just may survive to spend another day exploring Sag Harbor.