The Hamptons had been on my list for quite some time, so I was over the moon when I got to visit the fabulous beaches of Long Island. From Westhampton to Montauk, there are so many different "vibes" in the Hamptons. We did not get a car, which meant finding a town that was walkable. After diligent research, we settled on Southampton, mostly due to it's famous beach (Cooper's) and the shopping. After indulging in an iconic lobster roll from LUNCH and riding bikes along Meadow Lane's green hedges, I was completely charmed. Visiting in the summer is clearly ideal, but the Hamptons in fall also looks beautiful!
THURSDAY
Catch a train on the LIRR early out of the city. After arriving, drop your things at your AirBnb or hotel before heading to town. Luckily our AirBnb came with bikes and so we were able to get around more easily.
There are countless places in town to get a lobster roll, but none are quite like one from the no-frills LUNCH. I prefer mine Connecticut style (served warm), with a beer from a Montauk brewery!
Now it's time to visit one of the best beaches in the U.S. (according to some survey I have never heard of until now). Cooper's Beach has made many appearances in pop culture over the years (Sex & the City, Gossip Girl, Summerhouse), so we were curious if it lived up to its lore. It was a lovely beach, but I prefer Seaside's white sands!
Regardless of where you pick for dinner, a reservation is highly recommended! For more upscale, check out the Southampton Social Club (not on Main Street) or Plaza Cafe (on Main Street). TIP: Southampton Social Club certainly has a party vibe, but on more quiet nights the prix-fixe menu is a great deal. Order the scallops!
FRIDAY
Breakfast in town can be found at the Golden Pear or the Southampton Cheese Shoppe! We ate breakfast at our AirBnb but both options came highly recommended by our hostess. Next time!
Now it's time to shop! Dragging my sister out of Roller Rabbit and LoveShack Fancy proved to be quite the challenge... so many shops, so little time. Always a sucker for the historical shops, Hildreth's has been open since 1842! They have darling gifts and fun home decor. And don't forget to check out the vintage shops!
After getting your fill, Sip 'n Soda is the perfect lunch spot. It looks exactly the same as when it first opened in 1958. Try its Famous Lime Rickey drink and split a burger! TIP: Sip 'n Soda is cash only. TIP #2: If you prefer something healthier, pick up a salad or sandwich at Citarella Gourmet Market next door.
Still hungry after lunch? Satisfy your sweet tooth with a trip to the original Tate's Bake Shop. The Crumb Cake was to die for, but my sister opted for a cupcake. You can't go wrong.
For a lazy afternoon, check out a nearby winery. There are a few options, including the family-owned Duck Walk Vineyards and the beautiful Wölffer Estate. These were both highly recommended by our AirBnb host and will definitely be on the list for our next trip!
Finish off the day with a delicious Black & Bleu burger from Union Burger Bar. Add a fried egg and you won't be disappointed.
For a nightcap, check out the Southampton Publick House.
SATURDAY
You simply can't leave Southampton without having brunch at 75 Main! Located right on Main Street, be sure to make a reservation and request outdoor seating for prime people watching.
We headed back to the beach (you have a few other beach options), but there are also several museums in the area that are certainly worth a visit.
There are a few different Italian spots in town but we picked La Parmigiana. The baked ziti was fantastic, but the pizza also looked pretty tasty.
Fellingham's is the dive bar in town with its own softball team. It's certainly a fun spot to stop by after dinner, even just to take a peek at all the trophies.
ADDITIONAL RELEVANT TIPS
Getting around Southampton is generally easy. We used a combo of bikes, Uber and Circuit, a free golf cart service. If you don't have a car, be sure to book a place within walking distance.
Getting to Southampton wtihout a car, your choices are the Jitney or the LIRR. If you're coming from the west side of Manhattan, use the LIRR. If you're coming from the east side, the Jitney might be a better option. The LIRR is a bit cheaper and more efficient, but I'm sure everyone has their own opinion!
We stayed at the most picturesque AirBnb. It was in an old house that was built in the 1800s and had the sweetest host. It was a short walk to town, we highly recommend!
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