Real Housewife of New York City Kelly Killoren Bensimon guides us through one spectacular day on Long Island’s tony East End.
9:30AM - A Bookish Breakfast
Start your day in “East” (aka East Hampton) with a yummy scone at The Golden Pear Cafe (34 Newtown Lane) and then hit BookHampton (41 Main St.) for a newspaper or something salacious to read later on the beach.
11 AM - Retail Therapy
While you’re in town, visit Blue & Cream (60 The Circle) or Ralph Lauren’s Rugby (32 Main St.) for a cute summer dress or two. If you can squeeze it in, jump a few miles west to Wainscott to pick up a bikini and sunglasses at Tomas Maier (411 Montauk Hwy.).
1 PM - A Surfer's Lunch
Drop by Cyril’s Fish House (2167 Montauk Hwy.) in Amagansett for a quick and authentically local lunch of steamers, grilled shrimp and crab cakes. Then check your mood and energy level. Opt to laze about at picturesque Wiborg Beach in East, or hit Wainscott’s Main Beach Surf + Sport (352 Montauk Hwy.) for a surfing or stand-up paddleboarding lesson or kayak tour.
3PM - Wine Country
Dry off and head to Wölffer Estate Stables (41 Narrow Lane E.) in Sagaponack for some afternoon horseback riding. The stables have four riding rings (including one indoors), a dressage ring and natural jumps. If you’ve never mounted a horse, the staff offers lessons for novices—and it’s always fun to wear riding pants, regardless.
5PM - Beauty Touchup
Clean up for dinner at the 138-year-old White’s East Hampton Chemists and Perfumers (81 Main St.), which stocks great beauty brands such as Bobbi Brown and my favorite, Kérastase.
6 PM - Divine Dinner
For a glamorous dinner, head west to this summer’s see-and-be-seen spot in Southampton, Nobu at Capri, in the Capri hotel (281 County Road 39A).
10 PM - Cocktailing the Night Away
To wind down the night, head way east to Montauk’s The Surf Lodge (183 Edgemere St.) on Fort Pond. It’s a laid-back, cozy, beachy place with driftwood, bookcases and picnic tables overlooking the pond, but it’s serious about its mojitos and reggae. And when you’re done, stumble upstairs to sleep in a subtly surf-themed room with a refined rustic vibe.
PHOTOGRAPHS BY STEPHEN LOVEKIN/GETTYIMAGES.COM (BENSIMON); JOE TERMINI (SURF LODGE); TAYLOR K. VECSEY/EAST HAMPTON PATCH (WIBORG BEACH); NATHAN KIRKMAN (IN VILLAS VERITAS)