Hamptons NY Summer Vacation 2016

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We recently took a family vacation to the Hamptons in New York and it was amazing. We had never been there before and when you google Hamptons NY, it’s crazy the amount of things to do that come up. My parents every year either rent a house or in this case, rented out 1/2 of a bed and breakfast as our family Christmas gift for both my family and my brother’s family. My mom decided 6 years ago that instead of buying Christmas gifts each year for everyone, they would provide a family trip.

Hamptons NY Summer Vacation / Things to do / Where to stay / Places to Eat / Hamptons travel

We are very lucky and it’s always fun during Christmas Eve when the kids open up the “where we are going on vacation” gift. She is already working on this years Christmas trip surprise for next year.

Hamptons NY summer vacation 2016

So the Hamptons are pretty spectacular. We took the Cross Sounds Ferry out of New London, CT to Orient Point, NY which was so much fun for the kids. The ferry is only about an hour from our house so you literally drive to the ferry, drive your car on board and then go hang out in the restaurant portion of the ferry or sit on the deck and enjoy the one hour and ten minute boat ride.Once we arrived in NY from the Ferry, we drove an hour to the 1708 House in Southampton where we were staying.

Hamptons NY summer vacation 2016

The 1708 House is a gorgeous restored Bed & Breakfast that is run by Skip the owner and is lovely staff. I would highly recommend staying here. My parents rented out the Annex portion of the B&B which had 4 bedrooms, 4 bathrooms, a kitchen and amazing sitting/family room. The interior is stunning and this staircase which lead to our bedrooms was amazing.

Hamptons NY summer vacation 2016

It was like having your own house but you still had access to the main portion of the B&B which had breakfast, afternoon tea, snacks and a fun game room in the wine cellar.

Hamptons NY summer vacation 2016

The kids spent so much time in the wine cellar playing chess and checkers. I loved the fact that they spent hours playing good o’l fashioned games rather than being on their cell phones.  Every afternoon we walked to Starbucks to get the kids a frappachino and they couldn’t wait to get back each day, play checkers and drink their “special drink.”  I told them don’t get use to this frappuccino business everyday. -ha.

Hamptons NY summer vacation 2016

The B&B is directly on Main Street in Southampton and literally within walking distance to over 30 amazing restaurants and shopping boutiques.

Hamptons NY summer vacation 2016

Hamptons NY summer vacation 2016

The town is filled with gorgeous bistros and elegant restaurants.

Hamptons NY summer vacation 2016

We spent each morning at Cooper’s Beach about a mile from where we were staying and the ride to the beach was stunning. The roads are lined with perfectly manicured shrubs and beautiful sidewalks.

Hamptons NY summer vacation 2016

One of the days we took a 20 minute ride over to Sag Harbor which is another beautiful town in the Hamptons. We had lunch and did a little shopping in the quaint little town.

Hamptons NY summer vacation 2016

Most of the ocean front property in Southampton is privately owned and it was difficult to see many of the amazing homes but that didn’t stop us from stalking a few of them one day.-ha. We took a ride one afternoon and just went “house looking.”

Hamptons NY summer vacation 2016

Every single home had amazing architecture and stunning landscape.

Hamptons NY summer vacation 2016

I saw this driveway and fell in love. Certainly a dreamy driveway entrance for sure.

Hamptons NY summer vacation 2016

Coming home from vacation is never fun but it’s always good to get back home and get back into your routine.

Hamptons NY summer vacation 2016

My grandparents stay home and hold down the “fort” when we go on these trips. My grandparents are home bodies and prefer to stay home. My parents take them to Vermont once or twice a year to stay for a few nights so they can visit with relatives and friends. Both of my grandparents are from Stowe Vermont so heading there to see family is what they look forward to each year. That is actually my grandparents Christmas gift from my parents each year, a trip to Stowe. My mom is all about trips and spending quality time together. I like her way of thinking ;). I will be back in a few days sharing things to do and places to stay if you are planning a trip to the Hamptons.




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  1. Does anyone stay with your grandparents while you are away?

    1. Hi, yes! We have a house sitter who sleeps there and stays during the day to care for all the animals plus both aunts come by twice daily to hang out, do meds and check on them. Our house is never empty! ha

  2. I wondered where your grandparents were. Hopefully they didn’t party too hard at home 😉

    Love the pictures!

    1. Yep too much travel for them, they would have been miserable. We have people who stay at the house and both my aunts visit them daily when we are gone so that keeps them in line and behaving. haha.

  3. Juanita in OH says:

    What a gorgeous family you have! The places you went looked like so much fun, especially the Alley Ristorante. The geraniums are wonderful they make it look so homey, like Mayberry RFD. Isn’t it odd how people from the same state have not visited such wonderful places? I wish I had and could. TFS your trip.

    1. Thank you Juanita! We had a great time and you are right, many times living so close to places, we often don’t visit. It’s amazing the things to do right in your back yard. The streets were all lined with beautiful flowers and everything was so clean. Would love to go back 🙂

  4. Looks like a lot of fun! That’s a neat gift idea. I like looking at little shops. Those homes look so beautiful! Thanks for sharing all the great pictures. It gives me a chance to see places I haven’t been.

  5. This looks like a lovely trip. Such beautiful scenery, and who would have known there was so much to do in the Hamptons!

    1. Thanks Crystal! There are definitely parts of the Hamptons that really have nothing to do but Southampton was by far full of great restaurants and shopping!

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