An Experts' Guide to The Hamptons

In celebration of Drake’s Hamptons pop-up and collection with Clementina, my brand of tailored clothes for women, we encourage you to explore Long Island’s East End and visit some of our favorite places. 

When I only have a day and need to get out of the city, I wake up at sunrise and drive out to Long Island. Usually on a Saturday, any time of year, and in any weather except pouring rain. Many people look confused when I tell them I drive out for the day, around 2.5-3 hours each way. But this makes visiting the ocean more realistic when work and life get busy. I have favorite stops in each town that we’ll explore here.

Any experience that you find therapeutic affords you some delusion. For me, that’s overlooking 495 traffic. I grew up near the ocean and will do anything to be near salt water. The longer I live in the city, the more important this becomes. I rented a house in Montauk over a decade ago, learned to surf, cooked my meals on the beach, and now the whole area has become a big part of my life.

I love the Hamptons for its vast beaches, lush nature, classic homes, quiet character and tasteful atmosphere. It’s elegant all around, and any of its downsides are incredibly easy to avoid, even in August. September through May is my favorite time here or in any coastal town.

I’ve spent a few years traveling around looking for alternative seaside places, and finally found a few I really love in France (Brittany and Basque Coast) and Italy (Argentario) but Long Island has my favorite beaches anywhere.

Southampton is the first stop.

-Citarella: for newspapers 

-Gin Beach: my favorite LI beach: quiet year-round and always pretty—from the drive there, to the surrounding architecture, the neighboring lake, and the beach itself. 

*Plus secret permit-free parking across the way if you’re pass-less in summer.

-Hildreth’s Department Store: apparently America’s oldest. If only all dept stores were this refined and small!

Sagaponack

-Loaves & Fishes: charming for (pricey) prepared food for the beach, and gifts for friends. It reminds me of France and there’s usually a great local in an old car pulling up.

-Pike Farm & Marilee’s Farm Stand: down the street from Loaves and attractive produce when open.

East Hampton / Amagansett

-Carissa’s: I stop for breakfast or lunch, they close at 3pm. Everything is high quality, design equally great. But it’s some of the only good food around so it gets busy. I pick up their Pickled Rye loves for friends in NYC. Even the salad is my favorite anywhere. Baguette, nicoise sandwiches, whitefish salads, charred fish, shakshuka—all good. During high season (now) I avoid peak times.

-Book Hampton: for beach literature from a very passionate and refined owner. 

-Georgica Beach: Second favorite. Vast, beautiful, sleepy beach with limited cell service. If it’s windy out, I walk around the lake.

-Maidstone Beach: Really pretty. I mostly just like driving past Maidstone golf club, though I don’t care much for golf, the setting is unusually appealing.

-East Hampton Main Beach: Great off season or with kids bc of the shingled snack bar - elegant looking with the usual fried suspects.

-Egypt Beach: So quiet, so nice. Permits only! 

-S&S Corner Shop: In Springs, for coffee, artwork, books, groceries. Big Sur feeling.

-Two Mile Hollow Beach: An old-world, wood-shingled feeling and sleepy year-round. Where we hosted our Drake’s bonfire!

-Il Buco: For sea salt and coffee.

-Balsam Farm: For produce, and the location in Montauk too.

-Sabah: To pick up Turkish slippers and towels.

-Doubles: Everyone’s favorite casual spot for Caribbean-inspired food (roti, salads, and sandwiches!)

-Amber Waves Farm: For early morning coffee and eggs outside on the lawn.

-Love Eats: A healthy grocer that carries food from some West Village favorites: Bonberi and Spring Cafe Aspen.

-Clam Bar: A roadside classic for lobster rolls and fish. 

Sag Harbor

-Serene Green Farm: Lovely produce, thoughtful groceries, local/naturally made cookies. Next to a nice little beach stretch.

-Provisions: The old-school health food store with a casual cafe—one of the few remaining places for beach-adjacent tempeh. 

Montauk

*An overnight destination for any surf-loving person. 

-Shadmoor Reserve: This path on the ocean is remarkable. I’ve spent an enormous amount of time here, training for marathons, carrying surfboards, hiking, carrying logs down to cook on the beach. Sad to see it starting to wear down. This alone is worth a MTK visit.

-Naturally Good: similar to Provisions in Sag Harbor (groceries, prepped food, made-to-order). I find their food better than Joni’s.

-Joni’s: Casual institution that’s still good, healthyish to-go salads, sandwiches, breakfast, nice to sit at the picnic tables. Good vibe.

-Bambi’s: For breakfast/coffee, it’s run by two cool young Montauk women. Plant-based, GF, made in-house.

-Farmer’s Market at Duryea’s: The restaurant took a turn for the worse with new ownership, but the to-go and market is very, very good and the location can’t be beat.

-The Dock: A character-filled local dive-bar and restaurant that encourages no phones, no bullsh*t, and no screaming children.

-Marram: Nice to stay on the beach in the late Fall or early Spring.