By Kylie Monagan

This is the third in a series of  guides to the Hamptons by restaurateur Kylie Monagan.

Monagan, along with James Mallios recently opened Calissa, a new Greek restaurant in Water Mill. The inspiration comes from James' summers spent in Mykonos. This is James' third restaurant since he has opened Amali and Amali Mou in Manhattan. Before opening Calissa with James, Kylie was responsible for the operations of Amali and Amali Mou. While Kylie has been busy focusing on bringing the Greek Isles to the Hamptons, she has also made time to explore the eastern end of Long Island.

Photograph courtesy of Halsey Farm

Photograph courtesy of Halsey Farm

9am: Halsey Farmstand

Halsey is more than your average roadside farm stand. Located on Deerfield. just off the highway, it is the go-to for local chefs' produce and dairy needs. Don't miss their still-warm mozzarella cheese, beautiful heads of lettuces, and perfectly creamy avocados (I know, not local, but what's a day by the pool without a bowl of guac?).

513 Deerfield Road
Water Mill, NY 11976

Photograph courtesy of Pierre's

Photograph courtesy of Pierre's

Noon: Lunch at Pierre's

With just a touch of cliché, Pierre's also happens to make a delicious pastries and has sidewalk seating this is perfect for people watching. I like to order a bottle of Sancerre and a few croissants and see who passes by.

2468 Main Street, Bridgehampton, NY 11932
T: 631.537.5110

Photograph courtesy of Aerin

Photograph courtesy of Aerin

1pm: Shopping in Southampton

Southampton shopping is a healthy balance of chains and local boutiques. Fuel up with a mint and chocolate protein shake from Juice Press and hit these three favorites of mine:


Granddaughter of Estée Lauder and best known for her perfumes, this shop is the perfect embodiment of Italian Riviera meets NYC Park Avenue chic that defines the Hamptons. Look for delicate drop earrings and bohemian embroidered frocks -- just add an Aperol spritz and you've got the look down.

83 Main Street, Southampton, NY 11968
T: 631.353.3773

Club Monaco

This particular branch of the brand stocks one-of-a-kind vintage dresses and beautiful antique jewelry.

35 Main Street, Southampton, NY 11968
T: 631.283.0438


This is the original outpost of the collection that effortlessly nails “athleisure”. Jen Bandier's curated selection of funky tights, flattering bras, and perfectly ripped paper thin tees makes outfitting for brunch a breeze.

44B Main Street, Southampton, NY 11968
T: 631.488.4304

Photograph courtesy of Wolffer Estate

Photograph courtesy of Wolffer Estate

5pm Wölffer Estate Vineyard

This winery's package design is just as well crafted as their juice. Swing by the picturesque chateau for an early evening glass of wine and a cheese plate. I love sitting on the back porch and watching horses trot by as the sun goes down.

WINERY | 139 Sagg Road, Sagaponack, NY 11962 | T: 631.537.5106
WINE STAND | 3312 Montauk Highway, Sagaponack, NY 11962 | T: 631.537.4771

Photograph courtesy of Calissa

Photograph courtesy of Calissa

9pm Calissa

Taking menu and design cues from Mykonos favorites Scorpios, Kiki's, and Sea Satin, Calissa brings the bohemian beach chic of the Greek islands to the 6-3-1. Start with one of the unbelievably refreshing cocktails like the Altair (basil, watermelon, strawberry, vodka) before moving to one of the many large format wines. Lobster bucatini, kalamaki brisket, and salt baked montauk black bass are standouts and everything is best shared for the table.

After dinner, head to Calissa's sunset terrace for bottles and live entertainment and music (the lineup this summer includes DJ Lee Kalt, the Gipsy Kings, and the Casablanca Party with bellydancers, snake charmers, and live music).

1020 Montauk Highway, Water Mill, NY 11976
T: 631.500.9292

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