When you think of the Hamptons on New York’s Long Island, perhaps you are imagining a glamorous celebrity pool party with mimosas and an all white dress code. At least, that is what I have always imagined. So naturally it only made sense for me to plan a family vacation for the six of us (including one very talkative 5 year old, a wild 2 year old, and two newborn breast feeding twins) and schelp them all to the most glamorous beach getway on the east coast. And yet I am so glad we did!
Why go to The Hamptons:
For us, the answer was simple. We wanted a quick getaway in a location near sister’s house in New Jersey where we were staying for the summer. And although the traffic conditions can be crazy, the Hamptons are less than a 3 hour drive from her house and was a manageable drive for a family of six.
The Hamptons really does have something for everyone! So a quick background, the Hamptons are technically made up of only two townships: Southampton and East Hampton with several smaller villages and towns with them including Westhampton Beach, Sag Harbor, Hampton Bays, Bridgehampton, Amagansett, and Montauk just to name a few.
Westhampton Beach
Our first stop off the Long Island Expressway was John Scott Surf Shack for lunch. We had fish tacos and fish and chips and it was the perfect first meal on the island (bonus points if you can spot our stroller in the photo below). It was still early enough for a walk along the beach, however the only parking was at Pikes Beach and it is $40 for the day (there is no street parking on Westhampton Beach) so we moved along. But we heard good things about both Pikes Beach and Cupsogue Beach. We headed east by way of Dune Road all the way to Hampton Bays which is a fun drive to gawk at multi million dollar beach homes along the beach.
Southampton
Our next stop was Southhampton. Montauk Hwy turns into Hill Street which was pretty drive and it was around this point that my jaw started dropping as I looked around at the perfectly manicured landscaping and gorgeous homes. We headed to Halsey Neck Lane to hit up the famous Cooper’s Beach. Parking once again was $50 a day so I turned to Will and said, let’s try one other spot first. I had heard that right down the road there were two other parking areas: Halsey Neck Beach and Road D Beach. Halsey neck you need a residential permit but to our surprise and delight, Road D Beach did not and we got the last spot on the row. It was about 1pm on a Wednesday in July but we had the beach all to ourselves! I highly recommend checking out Road D Beach in Southhampton, especially since parking is so $$$ or hard to come by! Fluffy white sand for miles!
After the beach we loaded back up and headed into Southhampton Village. It’s a cute little downtown with tons of high end shopping. Our stops included Tates Bake Shop (although they were already closed for the day), Love Shack Fancy for me, and Sant Ambroeus for ice cream for everyone (I recommended the mango sorbet, it was amazing!) During a quick breast feeding/diaper changing situation we even found a playground at Agawam park for the kids.
East Hampton
East Hampton was the location of our AirBnB so we decided to head there next and get settled in. We were too tired to go out to eat but our options would have been pizza at Sam’s. burger and fries at Indian Wells Tavern. or more fish tacos at Bostwick’s Chowder House. The next day however was chalked full of delicious eats including starting our day with bagels from Goldbergs.
note: we ate at two separate Goldbergs while on this trip. The one in Southampton had horrible service and was so disorganized. However this one in East Hampton on Pantigo Place Road was a superb experience!)
Amagansett
Five minutes up the road from East Hampton is the tiny town of Amagansett. The main street area is cute and has some shops and resturants worth checking out if you are staying near this area. But the main draw, in my opinion is the Lobster Roll, also know locally as “Lunch” and perhaps made famous by its many appearance on the hit Showtime show “The Affair.”
We had lunch here on day two an it was so family friendly, great service, and an amazing lobster roll (Will got the hot lobster roll and I got the classic roll and we went half/half. I still can’t decide which I like better!)
Between Amagansett to Montauk
The drive from East Hampton to Montauk, through Amagansett which was about 20 minutes, was one of my favorite scenic drives the entire trip. Small farms and vineyards all along the way. You’ll pass Vicki’s Veggies which is adorable and worth a stop if you want to grab some fresh produce. Napeague State Park was also on our short list for some hiking opportunities but we decided to pass on this for this trip.
Montauk
The piece de resistance of the Hamptons is by far Montauk. Knowing what I know now, I would love to come back and do just a week here! Unlike the more upscale East Hampton and Southampton village, Montauk, which is an old fishing village, has a much more laid back feel. Don’t get me wrong, there is still big money here but it just felt more of my style.
Again, the parking situation is not ideal. You are not allowed to park on the street and the widely popular Ditch Plains Beach is residential parking only. Luckily we circled around til we found some local surfers and found free parking off Emerson Avenue and got to the beach using the beach access next to Bounce Beach Resturant. Here we were able to walk the shore line, watch all the surfers ride in the waves, and the kids enjoyed climbing the big rocks, in addition to trespassing on private steps 🙂
In addition to our morning at the beach, we spent some time visiting the Montauk lighthouse. Definitely worth a drive out to the “end of the word.” My favorite photo from here is actually the 6 of us in the parking lot with the light house behind us, but we also walked a small trail (right of the gift shop) and were able to get to the beach and see the lighthouse behind it which was another great viewpoint.
After lunch at the Lobster Roll, we decided to drive back into Montauk and drive around for a bit so the kids would nap. We drove the loop around West Lake Drive probably three times. The photo below is from the marina on Star Island. We also stumbled upon the most gorgeous wall of hydrangeas in front of the North Harbor condos of all places. Our last stop of the day was Shadmoor State Park to hike out to the cliffs but for many reasons #kidsandcliffs we decided to save this for another day. For dinner that night we headed to Montauket overlooking the Fort Pond Bay to watch the sunset on the bluff and thats how we ended our day!
All together it was an amazing trip. A few hiccups along the way and we only tackled about 1/8th of what is on our proposed “itinerary.” But sometimes you just have to go with the flow, toss the entire list out the window, surrender to defeat, and just drive around in circles. Nobody will ever tell you traveling with kids is easy. But then there are days that all four fall asleep in the car, so you put on some good tunes and keep driving until you find yourself on a side road full of rows of hydrangeas and stunning views of the ocean. It most definitely isn’t easy but if you slow down, take a deep breath, and look around, you will find it can still be pretty magical too.
