Hamptons day-trip ideas: Get the experience without shelling out for a hotel
If you can’t commit to the three-night minimum required at most Hamptons hotels, consider a day trip. You’ll be surprised at how much you can see, do, eat and buy in the span of a few hours before heading home to sleep in your own affordable bed.
Southampton
Credit: Gordon M. Grant
Start your morning with a muffin at iconic Tate’s Bake Shop (tatesbakeshop.com). Then plan strategically to enjoy an ocean swim. Some beaches prohibit parking for nonresidents. Two that sell day passes: Mecox in Bridgehampton and Sagg Main in Sagaponack. Maybe a better option: Rent a bike (rotationsbicyclecenter.com) and head to picture-perfect Coopers Beach, pictured.
Southampton
Credit: Gordon M. Grant
Back into the village, grab an al fresco lunch at casual bistro Little Red (littleredsouthampton.com) or Kardashian-approved 75 Main (75main.com). Dream of dressing like a Southampton socialite? Visit high-end consignment shops Collette (colletteconsignment.com) and The Perfect Purse (27 Hampton Rd.).
Southampton
Credit: Gordon M. Grant
Then stop by the Parrish Art Museum (pictured, parrishart.org) in Water Mill to enjoy an impressive collection of works by Hamptons-affiliated artists including Willem de Kooning, Jackson Pollock, and Roy Lichtenstein. Other nearby cultural institutions include the Southampton Arts Center (southamptonartscenter.org), exhibiting local artists, and Robert Wilson’s Watermill Center (watermillcenter.org), which offers tours of its collection as well as performances by artists in residence. For an intimate dinner, end your day at Tutto il Giorno (tuttoilgiorno.com). To experience a wilder side of the Hamptons, choose tacos and tequila at Union Cantina (unioncantina.net).
Sag Harbor
Credit: Gordon M. Grant
Enjoy a doughnut from Grindstone Coffee and Donuts (pictured, grindstonecoffeeanddonuts.com) on a Main Street bench while perusing a free glossy magazine, or walk to Marine Park and eat overlooking the yachts. Rent a bike at the Sag Harbor Cycle Company (sagharborcycle.com) and cruise over the bridge to Long Beach for a swim. Or take a mountain bike to nearby Barcelona Neck, just off of Route 114, which has seven miles of trails. For lunch, pop into Harbor Market and Kitchen (harbormarket.com) for a thin-crust pizza. Or try Sag Harbor’s excellent drive-in joint, Bay Burger (bayburger.com).
Sag Harbor
Credit: Randee Daddona
To learn about the village’s history and architecture, download the Sag Harbor Walking Tour app (available on iTunes), which will take you past gems, including the Custom House (pictured), John Jermain Library and the Old Whalers’ Church. Pick up a cookie at the Sag Harbor Baking Company (51 Division St.) and a coffee from Jack’s Stir Brew (jacksstirbrew.com) next door and then spend some real money. Sag Harbor is a decorator’s dream, with design and antiques stores galore including Ruby Beets (rubybeets.com) and MONC XIII (monc13.com).
Sag Harbor
Credit: Gordon M. Grant
Make a stop at the educational Sag Harbor Whaling & Historical Museum (pictured, sagharborwhalingmuseum.org). Then enjoy an early dinner at wine-centric Wölffer Kitchen (wolfferkitchen.com) before taking in a show at the Bay Street Theater (baystreet.org). Not ready to leave the Harbor just yet? Murf’s (64 Division St.), the village neighborhood bar, is open every night until 4 a.m.
East Hampton
Credit: LongHouse Reserve
Daily parking passes are limited at East Hampton beaches, so grab some bagels at Goldberg’s (goldbergsbagels.org) in Wainscott and head to Main Beach or Two Mile Hollow Beach before 11 a.m. to nab a spot. Have a late lunch at Citta Nuova (cittanuova.com), which has salads, sandwiches and sidewalk tables perfect for people-watching. Pick up some souvenirs: The Monogram Shop (themonogramshops.com) will personalize beach towels or a crystal ice bucket and stocks cocktail napkins with messages to the tune of “Have you seen my contractor?” Blend in with the locals in a block-printed tunic from Roberta Roller Rabbit (robertarollerrabbit.com). For some culture in the great outdoors, check out the LongHouse Reserve (pictured, longhouse.org), a 16-acre sculpture garden with pieces by Buckminster Fuller, Yoko Ono and Willem de Kooning.
East Hampton
Credit: Gordon M. Grant
Or if you want to get wet again, there is always stand-up paddle boarding with Paddle Diva (pictured, paddlediva.com) at Shagwong Marina. Nearby Harbor Bistro (harborbistro.net) is a picturesque place for a post-paddle drink and some oysters on the half shell.
East Hampton
Credit: Yana Paskova
Dinner at The Living Room (pictured, themaidstone.com/restaurant) will give you a chance to admire the view of Gardiner’s Mill, reflected in Town Pond. If you’re looking for some night life, head down Route 27 a bit to the Stephen Talkhouse (stephentalkhouse.com) in Amagansett, an unpretentious venue that has hosted world-class acts including Paul McCartney and Patti Smith.
Montauk
Credit: Gordon M. Grant
A perfect day in Montauk might start with an acai berry smoothie at surfer hangout Happy Bowls (805 Montauk Hwy.). Energized by superfood, hike the breathtaking cliff-side trails high over the beach at Shadmoor State Park. If you’re afraid of heights, choose Hither Hills State Park (pictured) instead, where you can either lounge on the beautiful beach or explore the Walking Dunes Trail, an easy 2.7-mile loop that can be done in flip-flops. Have fish tacos with the entire population of young Brooklyn at Tacombi (tacombi.com), Montauk’s trendy Mexican joint.
Montauk
Credit: Gordon M. Grant
Visit the Montauk Lighthouse, the oldest lighthouse in New York, having been authorized by George Washington in 1792. Climb the 182 steps to the watch deck and tour the 1860 keeper’s house with its display of historic documents, including one with Washington’s signature. Quench your thirst back in town with a sampling of seasonal beers at Montauk Brewery’s tasting room (montaukbrewingco.com). Then browse the vintage-style Montauk souvenir T-shirts and hoodies at Montauk Mainstay (montaukmainstay.com).
Montauk
Credit: Gordon M. Grant
Don’t miss the sunset on the deck of hipster hotspot the Surf Lodge (thesurflodge.com). Or dine on lobster rolls at newly renovated Duryea’s (pictured, duryealobsters.com) before heading home.
North Fork
Credit: Daniel Brennan
Stop along the North Fork’s Main Road to enjoy fluffy biscuits at Main Road Biscuit Company (mainroadbiscuitco.com) in Jamesport or grab a cup of fair trade coffee at the North Fork Roasting Company (noforoastingco.com) in Southold. Admire the pretty farm stands and intriguing antique shops that dot the route. When you arrive in Greenport, take a walk along its picturesque waterfront, whose deep protective harbor made it a center for whaling and shipbuilding in the 18th and 19th centuries. Hop on the antique carousel in Mitchell Park. There are plenty of lunch choices — Lucharito’s (lucharitos.com) for Mexican, the Little Creek Oyster Farm (pictured, littlecreekoysters.com), where you can shuck your own.
North Fork
Credit: Randee Daddona
Stop at Lavender by the Bay (pictured, lavenderbythebay.com), in East Marion, one of the largest lavender farms in the United States, where you can tour the fields and take home sachets, soaps, and bunches of dried lavender. Cool off at 67 Steps Beach, on Sound Road. Raise a cocktail glass to Greenport’s place in Prohibition history at Brix & Rye (brixandrye.com), the village speakeasy. For dinner, there’s excellent local seafood at Noah’s (chefnoahs.com) on Front Street.
North Fork
Credit: Nicole Horton
Wineries within a few miles of the town center include Kontokosta Winery (pictured, kontokostawinery.com), Bedell Cellars (bedellcellars.com) and Lenz Winery (lenzwine.com). Instead of driving, rent a bike (greenportbikerental.com) to get from one tasting room to the next.

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