The Hampton enclaves, from Southampton in the west to Montauk on the eastern tip of Long Island, and the stretches of country roads that connect them, are equally characterized by their relaxed, casual sensibility and small-town charm. And, thanks to a spate of recently renovated roadside inns with luxurious amenity offerings, you no longer need to enter the summer rental pool to weekend in the Hamptons like a true insider. Here, 17 steps to your perfect long weekend in the Hamptons.
Beat the weekend rush and head out midday Thursday. If you time it right, you can make the roughly 90-mile drive from LaGuardia airport in under two hours. (This same drive can take close to four hours during as the day wears on and the weekend grows near.) Prefer public transportation? Hop on the Hampton Jitney, a motorcoach service that runs from New York out to both the north and south forks of Long Island, or take Long Island Railroad.
Grab a late lunch at LT Burger in Sag Harbor (don’t miss the smoked gouda fries) and shop the charming boutiques on Main Street, including the Sag Harbor Variety Story, a family-owned five and dime with everyday essentials and throwback appeal, and Harbor Books, where you can sink into perfectly worn leather chairs with coffee and a classic book. (Bonus: Harbor Books offers a concierge service that will curate and install mini-libraries, such as children’s classics for a new baby or nautical reads for a yacht.)
After 3 pm, check into Baron’s Cove, the harbor front inn that first opened in the 1960s, has hosted well-known guests such as Paul Newman, Jackson Pollack, and Kurt Vonnegut, and has made one seriously stylish comeback, thanks to Colleen Bashaw and Cape Resorts. For prime sunset watching, ask for a harbor room (which come with gates that open to the pool area).
One of the best parts about Baron’s Cove? The complimentary bicycles available to all guests. Take one for a spin around town to check out the historic sea captain’s homes and other drool worthy cottages (for water views, follow Water Street to Redwood Road, which makes a loop). Other bike-able destinations: the Sag Harbor Whaling and Historical Museum and Havens Beach.
Wrap up your ride with a glass of rosé on the terrace of the The American Hotel. Built in 1846 at the height of the whaling industry in Sag Harbor, it remains the spot for people watching while soaking up what remains of the town’s Victorian elegance. Follow drinks with modern Italian (and seafood-heavy) fare at Dopo La Spiaggia (“after the beach” in Italian). 631-725-7009
It’s time to hit the beach! Fuel up with coffee from Sag Town Coffee, and then get an early start to snag a parking spot at one of the Hampton’s gorgeous public beaches, like Main Beach in East Hampton—or, skip the hassle of driving and take advantage of Baron’s Cove’s complimentary shuttle, chairs, umbrellas, and towels instead. Before you go: swing by Cavaniola’s Gourmet for beach picnic staples like sandwiches, salads, cheese, and crackers.
When you’ve had enough sun, head to the village of East Hampton for some refreshments and shopping. First stop: Scoop Du Jour for ice cream or indulgent cream frozen yogurt (bring cash!). Next up? The super stylish shops, like Mecox Gardens, the Monogram Shop, Lisa Perry, and Big Flower to name a few. Bonus: even chains, like Club Monaco, J. Crew, or Restoration Hardware, have a quaint, boutique feel.
On your way back to Sag Harbor, drop by our inspiration-filled 2016 Showhouse, where designer Meg Braff deftly weaves intricate patterns and bold colors in every room. The home features seven bedrooms, eight full baths (all with incredible tile work), a beautiful pool and breathtaking pool house, and enough decorating ideas to fill countless Pinterest boards. Tours (buy tickets here) run Thursdays through Sundays from 10 am - 5 pm through Labor Day weekend 2016.
That is, unless you feel like splurging on a sunset cruise on Hinckley yacht with up to six friends. That’s right, guests of Baron’s Cove have access to the ultimate Sag Harbor experience—exploring the area by private boat tour—thanks to the hotel’s partnership with Barton & Gray Mariner’s Club, a member’s only club that’s works essentially like ride-sharing for yachting set. The price is steep, but the payoff is huge: a private, captained cruise to nearby Sunset Beach or around Shelter Island.
After breakfast at Baron’s Cove, drive out on the Montauk Highway to the Montauk Point Lighthouse, the country’s 4th oldest continually operating lighthouse located on Long Island’s eastern most point. Admission, which is $10 for adults, $8 for seniors, and $4 for children, gets you in to the museum and up the 137 steps to the top; parking costs another $8. (Refuel break: break up the 20-mile, 35-minute drive with a stop at the Montauk Bake Shoppe for coffee and almond biscotti.) Don’t miss: the Napeague overlook next to Hither Hills State Park on the way out to the lighthouse.
Pull over for lunch at the Lobster Roll, (better known as LUNCH, thanks to its iconic sign) just before you get to Amagansett. This 50 year-old institution is the place for lobster rolls—get there early to beat the rush, then choose between two types of sandwiches: the “classic” lobster roll, a salad-based sandwich served cold, or the hot buttered lobster roll, which features whole pieces of lobster served with drawn butter.
One the way back to Sag Harbor, make time for a small detour to Sagaponack’s Madoo Conservancy, the two-acre private gardens (and the 18th- and 19th-century buildings-turned-studios) of deceased artist Robert Dash. Some highlights: the boxwood knot garden, the Pagoda-covered bridge, and brightly-painted garden structures (such as gates and ladders) that appear to grown out of the sea of green.
Spend the rest of the afternoon antiques shopping in Sag Harbor. Be sure to visit: Ruby Beets (a mix of midcentury furniture, custom upholstery, and fabulously oversized lighting); Sage Street Antiques (collectors take note: the inventory of quirky antiques and accessories changes nearly every weekend); and Bloom (the laidback sophisticated style starts with cottage exterior and winds through every detail of the shop’s interiors.).
Unwind over bar bites and drinks (try the Baron’s Mule, a refreshing, lemony twist on the classic) on the terrace at Baron’s Cove while you watch the sun tuck in behind the yacht-dotted harbor. Hungry for more? Head upstairs for dinner after dark.
After a morning dip in the Baron’s Cove pool, make your way to Bridgehampton for brunch at Pierre’s—a French bistro with all of the panache of a Paris café minus the stuffiness. Ask for a table outside on the street, start with coffee (served with a square of Belgian chocolate), and enjoy an extra leisurely brunch with a side of people watching. Before you go: pick up sandwiches and cookies from the adjacent bakery for the road.
On the way to the airport, or back to the city, make one last stop at the Parrish Museum in Water Mill. The building—a pair of elongated wings made of poured concrete walls and topped with gabled, metal roofs that tuck into the gently rolling hills and stretch out across a meadow of wildflowers—is itself worthy of a visit, not to mention the collection of nearly 2,600 American paintings from the nineteenth-twenty-first centuries.