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
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.
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.
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.