Hamptons, New York (Sterling Boyd)

• 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.

Where to Eat and Drink

• Check out the local newspapers for the weekly listing of farmers markets. We particularly loved the farmers market in Sag Harbor and Southampton. Look for fresh fish, fruit, veg and delicious pies.
• Post beach, take the family to Bridgehampton Candy Kitchen for homemade ice-cream. It is DELICIOUS. Try the peach, coconut, mint chip, coffee...you get the drift. It is all good.
• We are always on the hunt for a good spot to have breakfast with the family post 6 am wake-ups. We love Estia's Little Kitchen. How can you not like a place where the infamous breakfast burrito is named "Big Al' after local Alec Baldwin. Get there early. It fills up and there are no reservations.
• When you marry an Englishman, you spend time researching where to find Fish and Chips. I'm happy to say that the Dock House in Sag Harbor is a winner. It is a tiny whole in the wall seafood shop that sells both fresh seafood and has about 20 bar chairs for a casual meal. You can also take your food and have a picnic on the pier. Super casual and local, but perfect for a night with the family.
• See "Do" for more food suggestions...

What to Do

• Friday night at Wolfers Wine Stand. Every Friday and Saturday at 5pm, you can bring your blanket, chairs and picnic food to enjoy live music in the vineyard at sunset. Check out the website for the music lineup and don't miss it. It is quintessential Hamptons and we love it every time.
• Beaches, beaches, beaches. If you have never been to the beaches in the Hamptons, you likely don't realize how beautiful they are. Make sure to spend some time exploring all the beaches in the area for a walk, dip or just the view. Our favorite is Sag Main Beach. If your children are young and scared of big waves, head to the Noyack Long Beach. It is on the Peconic side and is perfect for little ones to dip their toes. Some advice - do your research before you start your trip. Many Hamptons beaches are private and/or are only open for visitors on specific days. And most charge a fee. Make sure the house you are renting has access to a beach or check the beaches in your area to make sure you know when they are open to the public.
• On a really hot or rainy day head to Children's Museum of the East End. It is a perfect activity when you need a little break from the beach.
• Take a wander around the Hamptons towns - my favorite is Sag Harbor (although make sure you also do Southampton and East Hampton). My favorite shop in Sag Harbor is Stella and Ruby for kids clothes. They have some amazing brands and things you won't find anywhere else. They also have great interior shops. Stop at LT Burger with the family for milkshakes, burgers and fries. Always a winner.
• A day trip to the sleepy little town of Greenport on the Northfork. We generally stay in Sag Harbor, so this trip is just manageable for us with little ones. Take the ferry to Shelter Island and make a stop at Marie Eiffel Market where you can sit out on the dock for coffee or lunch. Take the ferry from Shelter Island to Greenport for a ride on the Antique Carousel and lunch at Lucharitos (tacos and killer margaritas for the folks not driving!).

inside scoop

Get wine shipped to your rental in advance. The local markup is about 20% – 25%.

skip it

Highway 27 at mid day. The traffic will kill you! Plan your day to get out early in the morning and then use the backroads in the afternoons. It will keep you moving and the kiddos happy.