Winter Staycation Guide to The Hamptons and Montauk
Even though we both grew up on Long Island, we had never really been out east to the Hamptons & Montauk. Can you believe that?! We thought to celebrate our 5 year anniversary, it would be the perfect opportunity to do a little staycation somewhere we’ve never been! If you know us, you know we love beaches & beach towns (yes, even in the dead of winter haha) so we figured The Hamptons would be a perfect place to celebrate! The Hamptons really thrives in the summer and is known for it’s rich & famous clientele, but sometimes it’s nice to visit a place during the off-season — especially during the pandemic — when you can easily avoid crowds. And you know what, it’s nearly just as fun. So here are our tips for visiting Montauk & The Hamptons during the winter!
How to Get to The Hamptons
We drove to the Hamptons from NYC, but it’s very easily accessible by train as well. You can take the LIRR to a bunch of towns in The Hamptons or Montauk if you don’t have access to car.
Where to Stay in The Hamptons
We chose to stay at an Airbnb because we like having an entire place to ourselves (especially during COVID), but there are a lot of hotels & other accommodations in Hamptons & Montauk too. We loved our Airbnb — it was spacious, had a fireplace & a fire pit, was close to the beach, and had an in-ground pool that would be amazing to use in the summer.
Best Things to Do in The Hamptons & Montauk
Explore the towns of East Hampton, Amagansett, Sag Harbor, Bridgehampton, & Montauk
Visit the Montauk Lighthouse
Take a walk on one of the many beaches
Do a wine tasting at Wöffler Estate Vineyard (tip: try the Rose Cider, it’s what they are famous for!)
Check out old & new records at Innersleeve Records in Amagansett
Pop into one of the many local boutiques (tip: most things are very expensive because of the wealthy people in the area, but you might be able to find a few decently priced things!)
Book other Hamptons & Montauk activities here!
Where to Eat & Drink
La Fondita
Mary’s Marvelous
Sagtown Coffee
Wöffler Estate Vineyard
Capaletti’s
Babette’s
Il Tutto Giorno
The Golden Pear
Provisions
We absolutely loved the Hamptons and are already planning to visit again in the summer when it’s warmer! For more info and tips, make sure you check out our vlog from The Hamptons & Montauk!
Our 5 Year Anniversary in the Hamptons
Disclaimer: We partnered with Airbnb for a portion of this post. Some links on this post are affiliate links of which we receive a small commission, but the price is the same for you.