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JOURNAL
The Hamptons Travel Guide With Annabel The Shop
If you’ve ever wondered how New Yorkers find reprieve from the city heat in summer, the answer is a weekend escape to the Hamptons in Long Island. Only a two to three hour transit from Manhattan (via train, car or jitney), the island is made up of a series of classic all-American beach towns – Bridgehampton, Sag Harbour, Montauk, to name a few – and each is only a stone’s throw from the other.
Together with our beloved Hamptons retailer, Annabel The Shop, and Annabel DeGroot, we share a local’s guide to visiting the Hamptons.
Where to stay
A quaint yet waterfront hotel in the heart of Sag Harbour village. Only walking distance to the wharf where you can watch the sun set over the ocean and the Main Street, lined with boutiques, cafes and restaurants.
For perhaps a slightly less relaxing experience and a more lively one, the Montauk Beach House is steps from the ocean and known to host some of the best summer parties and DJ events each weekend. This summer they are also hosting a poolside Annabel The Shop pop-up with new season FAITHFULL bikinis to shop.
The Pridwin Hotel & Cottages, Shelter Island
For the classic all-American experience, this is a beautiful historic hotel and waterfront restaurant tucked away on the hill of Shelter Island that has been open since the late 1920s. With bespoke rooms and private cottages, it is the perfect idyllic Hamptons stay away from the hustle and bustle of the beach crowds.
Where to have coffee and breakfast
Sagaponack General Store, Sagaponack
Only opening this past year, it has quickly become a favourite haunt of the locals. It is the perfect stop for a takeaway coffee and homemade cinnamon bun on your way to the beach.
For some simple yet delicious, it’s hard to look past this bakery and pantry in downtown Sag Harbour. Pick up a coffee and pastry (or even one of their famous lemonades) and bring it with you to the nearby park to soak up the sunshine and watch the boats sail in and out of the marina.
Estia’s Little Kitchen, Sag Harbour
Equal distance between our Sag Harbour and Bridgehampton locations, this is one of our favourite places to pop in for breakfast (or even lunch). They’re known for their delicious fusion of Mexican and American and are tucked inside a roadside-style cafe.
Just around the corner from our pop-up space at Montauk Beach House, this is the perfect stop for an iced coffee or matcha when you need a little summer pick-me-up.
Round Swamp Farm, Bridgehampton
While not a cafe or restaurant, you won’t find fresher organic produce in the area than at this country-style market, complete with a fish and seafood market, grocer and lovingly baked goods and pre-made meals.
Where to wine and dine
For a delicious, authentic Italian dinner, you must stop into this classic restaurant and enjoy a spritz on the patio, followed by burrata, flatbreads and our favourite rigatoni pasta.
A beautiful Greek taverna around the corner from our Bridgehampton location. We love to stop in on a summer’s evening and dine on their mezze platters and enjoy the laidback Mediterranean ambience they offer.
Bostick’s on the Harbour, East Hampton
For a relaxed dining experience with panoramic views of the harbour, visit this restaurant in the Springs area and order the baked clams with a fresh cocktail.
Where to swim
Ocean Road Beach, Bridgehampton
Our favourite spot in the Hamptons to swim, it offers classic stretches of crisp, yellow sand and calm seas. Park nearby and enjoy the day with an iced coffee you picked up on the way and a summer read.
Long Beach, Sag Harbour
If you prefer more of a bay-style swimming location, visit Long Beach later in the day when it begins to quieten down. It’s also one of our favourite spots to bring a takeaway dinner, collect seashells and watch the sunset.
Ditch Plains, Montauk
This is the infamous surfing location in Montauk. Nearby you’ll find a delicious food truck, Dutch Witch, where you can stop in to pick up a drink and snack after you’ve cooled off in the sea.
Sunset Beach, Shelter Island
For a taste of European summer in the Hamptons shores, visit Sunset Beach and Sunset Beach Hotel, accessible by ferry from Sag Harbour. You’ll instantly be transported to what feels like a French Rivieria beach club where you can sip delicious cocktails and even dance the night away.
Where to shop
You can find us currently at three different Hamptons locations – our boutiques in Bridgehampton and Sag Harbour as well as our pop-up at Montauk Beach House. You can discover new arrivals from the Summer 2025 collection, Letters From Hydra.
Lazy Point Variety, Amagansett
With an eclectic mix of handmade and vintage jewellery, clothing and homewares, everything inside this boutique is unique and sourced from all different designers – both in the Hamptons area and around the world.
This lifestyle store is just around the corner from our Sag Harbour location and offers a beautiful array of Mediterranean-inspired pottery, furniture, homewares, trinkets and accessories.
For an amazing array of curated vintage pieces, find this space in an outpost at The Montauket Hotel. We always love to visit as not only can you find some of the most special antique-style pieces but you can follow with a drink at The Montauket Hotel after, with live music and views of Fort Pond.