Hamptons, New York (Amanda Freeman)
South Hampton, East Hampton, Sag Harbor and Amagansett all have their own personalities... spend an hour or three (window) shopping in each town.
- More about your Oliver Guide: Amanda Freeman
- Trip type: Adult, Family, Group getaway, Beach
- Activity level: easy
- Ideal length of trip: WEEKENDS ALL YEAR, SUMMER SEASON
to & from
- Drive or rent your own car (you will likely want one)
- Take the Jitney (bus)
- Take the train
- Take a sea plane
- Take a Blade helicoper
Where to Stay
- Work with an agency or VRBO a house
- Surf Lodge in Montauk
- Gurney's Resort in Montauk
Where to Eat and Drink
- The Palm in East Hampton: chicken parm, lobster or steak. Apps: the Monday Night Salad or the Gigi Salad
- Suki Zuki in Watermill (sushi!!! the tuna sandwich and the chicken salad)
- Duryea's in Montauk (lobster salad, corn)
- Surf Lodge in Montauk (live music and drinks)
- Sunset Beach on Shelter Island (European-style drinks and food)
What to Do
- SHOP... South Hampton, East Hampton, Sag Harbor and Amagansett all have their own personalities... spend an hour or three (window) shopping in each town.
- Amagansett Square - charming shops, coffee shop and grassy area for kids to play while you shop!
- Poupette St. Barth, Milly, Calypso, Zimmermann, Figue (East Hampton)
- Matta, BookHampton, Collette, Jayson Home (Sag Harbor)
- Surf Lodge boutique (Montauk)
- Sunset Beach boutique (Shelter Island)
- Farmers markets...so many! (Fairview Farms in Water Mill - the best Challah ever)
- For Rainy Days... The Children's Museum of the East End in Bridgehampton
- Drum Circle in Sagaponack on the beach on Monday nights, gets crowded, but worth going once!
- SLT in Southampton and East Hampton (cardio+pilates studio)
Inside Scoop
- You need a beach permit to park at most beaches from Memorial Day - Labor Day.
- Traffic can be terrible, avoid the main road and take the side roads when possible.
- The earlier you go to Surf Lodge, the more likely you are to get in and not have to wait in line.
- Rent a boat for a few hours from Global Boarding, so much fun!
Sag Harbor- Hamptons, New York
There is something magical about the light out in the Hamptons, on the East End of Long Island. It feels like the essence of summer.
- More about your Oliver Guide: Sabrina Eliasoph
- Trip type: Adult, Family, Group getaway, Beach
- Activity level: easy
- Ideal length of trip: 3 nights or however long as you can
to & from
Fly to NYC (LGA, JFK airports) and drive out to the East End; watch out though for traffic, can be brutal if leaving to go out on a Friday in the summer and returning on a Sunday evening…
Or take Blade Helicopter service out from NYC airports to East Hampton
Or take Hampton Jitney bus from different NYC pick-up spots
Or take the Long Island Railroad out to Hamptons
And if coming from New England, Connecticut, etc., bring your car on the ferry to Port Jefferson from Bridgeport, CT – reservations in the summer are a must if traveling with your car.
Where to Stay
Baron’s Cove LOVE this awesome hotel, situated on the Peconic Side of Sag Harbor but within a 7-10 minute walk of Main Street. It is such a great hotel, with an awesome pool, very clean rooms that are nicely sized, a fun lobby/ bar scene, a yummy restaurant, AND such good service if you are choosing to go off campus to the beach. They will give you the parking permits for a few different Sag Harbor beaches and the hotel will set you up with chairs, towels, umbrellas, etc so you can go off and have a successful day at the beach without any hassle. Service was fabulous as well.
Where to Eat and Drink
- Dopo La Spiaggia Such an awesome restaurant with best atmosphere ever if you can sit outside in the garden. So romantic but vibey all the same and delicious food
- Wolffer Kitchen – restaurant from the local, beloved Wolffer winery, which in and of itself is a fun place to go wine-tasting. The restaurant in downtown Sag Harbor truly is pretty as can be, as are the rose bottles, and the food is yummy too.
- Loaves and Fishes – this is one of the most delicious places to pick up picnic foods but done-fancy… most delicious chicken and tuna salads, veggie salads, soups, breads, etc. It is a deli/ bakery but Hamptons style– so not just a typical place. Perfect place to stop and pick up lunch on the way to the beach but beware of long lines.
- Le Bilboquet- of the New York, Dallas, Atlanta fame, this is just a little French gem in a shingled single-story house serving up scene and some of the best moules frites around.
What to Do
Beach, beach, beach… so many of them! And you have your choice between beaches on the calmer, more mellow side of the Peconic Bay OR the wildly beautiful, vast Atlantic Beaches. The main beach at Sag Harbor is gorgeous; although if you find yourself nearby at Southhampton or East Hampton, the beach is the beach and they all share the same stretch of sand and surf. Be careful of heavy undertow though– these beaches have a strong current.
- Shopping.. between downtown Sag Harbor, Southhampton, East Hampton, think New York City at the beach.. and the shopping reflects that. There is a such a fun edge to all the boutiques out there on the East End.
- Museums- between the Parrish Art Museum and the Jackson Pollack- Lee Krasner House are just 2 examples but there are lots of cultural milestones and places to see)
- Biking- there are so many flat roads and trails and beautiful places to take in the scenery by bike
- Exercise- nearly every one of the great New York City exercise studios, like Soul Cycle, Taryn Toomey * The Class*, Tracey Anderson-- all have outpost studios in the Hamptons. The workout scene is nearly as good as it is in NYC. Definitely take a few hours to yourself pre-beach to hit one of the many fabulous studios to get your sweat on pre-beach.
Inside Scoop
- Parrish Art Museum – such a great place to spend a rainy afternoon; architecturally stunning and just such a complete cool collection of works of so many artists local to the region
- Drinks at the American Hotel in Sag Harbor– you will think they are copying Ralph Lauren’s Polo Bars in terms of atmosphere, but really this place is the real-deal; and has been around far longer than Ralph! 🙂
- Walking around is super easy and safe… we walked from hotel to town very easily back and forth each night.
- Certain beaches require permits so make sure to speak to hotel about which beaches they have access guests permits for.
- Farmers’ Markets- some of the best produce is grown out on the many farms of the East End of Long Island. The produce is fresh, delicious and so much fun to see in all of its summer glory at the various Farmers/ Fruit stands.
- Joey Wolffer: – This is an awesome boutique in Sag Harbor, owned by one of the family members of Wolffer Winery– eclectic cool finds, including clothing, home decor, gifts, etc.
What to Pack
Bathing suits & cover-ups for the beach
- Restaurants can be very chic, it is where many New Yorkers go after all, so definitely some fun dinner attire for which you'd even wear out in the city
- A sweater or light jacket- are you are out on the far point of Long Island, surrounded by water on all sides, it can be breezy night so bring a light jacket
More...
Be careful if you are going in off-season months to call and make sure any places you want to visit are actually open. Lots of people live out in the Hamptons year-round but high season is definitely summer. In the winter, many places close down.
Looking for some more Sag Harbor scoop? Check out summer local, Blythe Harris’ guide!
Sag Harbor-Hamptons, New York
We love going paddle boarding as a family on the bay in Sag Harbor.
- More about your Oliver Guide: Blythe Harris
- Trip type: Family, Beach
- Ideal length of trip: 5 DAYS
to & from
Fly into JFK and take the jitney, or Take the jitney from Manhattan. Rent a car (you likely will want one) at airport and head to the beach.
Where to Stay
- Barons Cove (Summer)- On the water with a pool, great bar and outdoor dining.
- The American (Winter) - Historic old hotel with a charming wood paneled bar.
Where to Eat and Drink
- The Beacon- right on the water, perfect for an adults night. Ask the bartender, Matty, for a Ruby Margarita.
- Murfs in Sag Harbor is a not-to-be-missed dive bar staple.
- Crows Nest In Montauk is a private beach on the bay where kids can explore while you wait for food.
- Town Line in Wainscott is perfect for kids and a casual night out.
- La Fondita in Amagansett has the best Mexican food. Try the tacos and the tostadas for lunch and let the kids run around the little lawn.
- We also love to take out lobster rolls from Fish Market in Sag Harbor and take them to Cameron Beach for a picnic.
- Sunset Beach on Shelter Island for cocktails and casual dinner-kids can play on the beach.
- Cavianolas in Sag Harbor- great takeaway salads and sandwiches.
- Bhudda Berry frozen yogurt shop in Sag Harbor is a crowd pleaser.
What to Do
- CMEE (Children's Museum of the East End) is a great resource-especially for an occasional rainy day.
- We love going paddle boarding as a family on the bay in Sag Harbor.
- The Whaling Museum in Sag Harbor
- The John Jermain Library in Sag Harbor is really special, worth a visit.
Inside Scoop
- Cameron beach is the BEST beach!
- You need a parking pass to park at most beaches.
More...
For a crash course on where to eat, drink and be merry in Sag Harbor, check out OG mega-contributor, Sabrina’a guide to this lovely town.
Sag Harbor-Hamptons, New York - Suggestions from the Oliver Community
- Courtney Leary Says
Visited recently (June) for the first time. Baron’s Cove was a perfect location and the food and drinks at the restaurant were great. Definitely recommend having a car — it made it possible to visit all of the other Hamptons towns at a moment’s notice and they are all worth a visit. Was so impressed by the shopping & the restaurants in all of the towns, including Sag Harbor.
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Hamptons, New York (Sterling Boyd)
We had no idea how much we would love the Hamptons. We fell in love with the area, the beautiful beaches, the copious farmers markets hiding behind every bend and the cute towns full of shops and delicious places to eat.
- More about your Oliver Guide: Sterling Boyd
- Trip type: Family, Beach
- Activity level: easy
- Ideal length of trip: HOWEVER LONG YOU CAN GO!
to & from
We live in New York so for us, travel to the Hamptons includes renting a car and leaving as early as we can to catch the afternoon rays at the beach. Otherwise, fly into JFK, rent a car and head out from there. Expect around two hours depending on traffic and where you are heading.
Where to Stay
- I always think the best option in the Hamptons is to rent a home with a pool. You get your own space and can balance beach going with lounging by the pool. Try airbnb, VRBO or splurge on Kid & Coe.
- If you are going for a short stay and need a hotel, our favorite is Topping Rose House. It is perfectly located in Bridgehampton close to Sag Harbor and Southampton.
Hamptons, New York (Amanda Freeman) - Suggestions from the Oliver Community
We stayed at the Maidstone which was very convenient to East Hampton with a great (not too busy when we were there in June) restaurant and bar- There are bikes that free to use and make it easy and fun to get around. (We rode to Amagansett for shopping and lunch!) Ask for a backroom or a cottage as the street noise can be bothersome. Small buffet breakfast in the morning is lovely and easy. It is not completely luxe but a nice option.
We LOVED Pierre’s for dinner in Bridgehampton. Si Si is new, in East Hampton, was a fun clubby scene with great food and large portions but save it for a sunny day, the evening we went it happened to rain and we missed the full effect of sitting on the water. Organic Crush is a great healthy lunch stop– grab and go- in Amagansett and don’t forget to stop by LazyPoint and Warm down the street for a quick (or long) shop. Be warned the portions at Duryea’s are HUGE (and the prices match) and are meant to share with a group of four! Bring friends and stay all day!
Citarella is a gourmet market with a couple locations in the Hamptons- great place to grab makings for lunch at the beach or if you have a house, an easy dinner.
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