This is not a typical Hampton vacation like you see on TV where we spend the day by the beach and attend glamorous parties at night. Our trip to the Hamptons with baby was geared towards getting a flavor of the area; discovering scenic drives and fun towns to complement our baby’s travel schedule.

Planning trips with an active baby is challenging in so many ways. Working around their sleep schedules is the easiest way to get from point A to point B. We looked for long weekend getaways that were around two to three hours away from our home in Westchester, New York, and planned the drive to coincide with his nap time.

One such trip was to the Hamptons in mid September 2012. Having seen beautiful pictures of the famous lighthouse we decided to spend two nights in Montauk. The whole trip was a series of drives while he napped interspersed with time for exploring on foot capped off with a meal that put him back in the mood for another nap while we drove further, seeing the sights from inside the car.

When to Go to the Hamptons

We decided to avoid the summer crowds and the exorbitant rates by traveling in mid September when weather was still warm.  April-May or September-October can be a good time to visit to beat the summer crowds and still experience beautiful scenery and pleasant weather.

Where to Stay

It was very difficult to find a hotel that didn’t have a 3-night minimum or a reasonable rate (less than $250) despite visiting after the busy summer season. After checking online and calling several hotels, I settled on Ocean’s Resort Inn as which offered a specious, two storied room that could accommodate a travel crib. The deck overlooking the ocean was great for calming the baby.

There are also several houses and condos that can be rented for a much cheaper price as an alternative.

What to See

Southampton: Having been made famous from many TV shows this is the biggest and the must see downtown. There are lots dining options and shopping on its scenic Main Street.  Stop by Tate’s Bake Shop for some of the freshest packaged chocolate chip cookies you will ever eat.

Shelter Island: The hour long trip to Shelter Island from Montauk includes a hassle free and low cost ferry ride that transports your car. A simple drives through the island offers spectacular views of the water and a window into island living. Though we didn’t stop for a meal we noticed several worthy options along the way.

Sag Harbor:  The downtown area was bustling even during off season. The town had a very community feel with many families going out and about. With a variety of cafes, book stores and specialty shops to choose from, you could spend a nice afternoon here.

Montauk: Seeing the view of the Atlantic Ocean from Montauk Point Lighthouse makes the hour long drive from the heart of Hamptons

worthwhile.  The park entrance fee ($9 for adults and $4 for children) includes visiting the lighthouse museum and access to climbing the tower. There is also a separate $8 parking fee per vehicle.

As young children are not allowed in the spiraling stairs, interested adults will need to take turns climbing to the top. The surrounding park is great for picnicking or just relaxing outdoors.

The public beach in Montauk was easily accessible from the main road though parking close by maybe a challenge.

Bridgehampton and East Hampton are two other well known towns with nice downtown areas and beautiful neighborhoods that we didn’t get to fully explore.

Where to Eat in the Hamptons

Silvers Restaurant:  Silver’s is known as the  place to lunch in Southampton that only serves lunch. They offered bistro fare with a spacious back patio to accommodate a stroller.

Sea Grille at Gurney’s Inn: An upscale hotel restaurant with an ocean view backdrop that is famous for seafood expertise. The staff was very accommodating towards babies; strollers were allowed in and high chairs were available.This can be a memorable dining experience for adults that welcomes babies.

Hampton Chutney: Freshly prepared South Indian fare with with dosas (crepe like food) being their specialty. Great lunch spot with outdoor seating.

Wok & Roll: Typical Chinese menu but a good option for eating in as we did after a busy day of sightseeing.

Though it has been on our travel list for a while, I’m glad that we waited to do this trip with baby. The drives were a perfect way to sample the different towns without being too demanding on baby’s schedule. Visiting off season helped us get a feel for the Hamptons lifestyle without the insane price tag.