Fall in The Hamptons: A 24 hour travel guide.

Hello Blondies!

The fiancé and I just got back from a quick getaway to The Hamptons. We were there for 2 days in the “off-season” so I thought I’d put together an itinerary for anyone who decides to take a quick day trip if you’re ever in the area and need an idea of what to do since it’s too cold for the beach and most businesses are closed for the season.

Where to stay: Sag Harbor


Sag harbor is a really cute old whaling town. It’s full of history. It is a great central location to stay, especially if you plan on venturing out of the Hamptons and onto the North Fork. We stayed at an AirBnB. Although, there are a few bed and breakfasts and of course, The American Hotel, which is typically booked so good luck getting a room there.

Let’s take a morning stroll through the town of Sag Harbor.

This neighborhood was so cute, I could not stop taking pictures.

Are you hungry? Stop in at the Harbor’s neighborhood market for a fresh organic breakfast or lunch. We realized not very many restaurants were open everyday. So it’s good to know that Harbor Market & Kitchen is open everyday and serves breakfast until 2 o’clock! How cute is this market?! They had everything from omelets, to soft-served ice cream, to wood-oven pizza.

Now that we’ve eaten, time to try some Long Island wine!

There are 3 wineries in The Hamptons, all the other hundreds of wineries are on the North Fork, but since this is just a 1 day itinerary we’re going to stick to our favorite winery by far: Wölffer Estate.

Wölffer Estate Winery is classy yet laid back. They are very proud of their vineyard and you will see the name Wölffer all over the South Fork of Long Island. Call ahead and book a tour, you’ll learn about the history behind Wölffer Estate and actually enjoy how family oriented it really is.

After your tour, sit outside and take in the breathtaking view of the vineyard while drinking wine of course.

Once you’re finished at the vineyard, head into East Hampton for a shopping spree on Main Street.

When you’re done shopping, go for a quick drive into Bridgehampton, drive around and look at all the pretty houses. Walk around get a little lost. Don’t forget to stop in at the Candy Kitchen for the best ice cream sundae you’ll ever have in your life.



If you’ve followed this itinerary to a tee, then by now it should be late afternoon. Take a drive to Montauk and go to Montauk Brewery Company. It’s a long drive (about 35-40 minutes) but it’s a pretty one, so roll your windows down and enjoy the sea breeze. After a few cold ones drive down to the easternmost point of Long Island and watch the sunset at Montauk Point.

This pretty much sums up a day in The Hamptons. Let me know if you’ve ever been! What did you do?

Until next time blondies… xoxo.

Published by

Leave a Reply