The Hamptons are a group of villages in the towns of Southampton and East Hampton along the south fork of Long Island, New York. The Hamptons have historically been a popular summer landing spot for elite NY socialites, celebrities, and business moguls alike. In fact, some of the country’s most expensive residential properties are located in the Hamptons.

There was no doubt we had to check out this little slice of (seemingly) heaven even for just a day!

First, lets get our bearings:

From Stamford, CT this should take about 1hr 45 minutes. However, once you hit Riverhead, you’re driving on a single lane road with bumper to bumper traffic so it took us nearly 3 hours to get into East Hampton

Southampton is comprised of Eastport, Remsenburg, Speonk, West Hampton Dunes, Westhampton, Westhampton Beach, Quogue, East Quogue, Hampton Bays, Southampton, Water Mill,Hampton Bays, North Sea, Noyac, Tuckahoe, Shinnecock Hills  a portion of Sag Harbor, Sagaponack and Bridgehampton…phew, that was a mouth full! Southampton is known for its shopping, oceanfront homes estates, and old $$.

East Hampton Town consists of Wainscott, East Hampton, Amagansett, North West Harbor, Springs, a portion of Sag Harbor and Montauk.  East Hampton is better known for its nighlife in Hamptonsand, boutiques, art galleries and celeb sightings. Further down the road, Montauk is a more family-friendly, sleepier town and is a surfer’s haven.

Getting lost among the estates in East Hampton with tree lined streets casting privacy among these homes create quite the mystique. Although trespassers are not welcome, deer freely roam up and down the roads and driveways with little grief.

For wine enthusiasts, there are actually quite a few vineyards in the Hamptons. To name a couple, Wolffer or Channing Daughters Vineyards, both in Bridgehampton just down the road a bit further than East Hampton. We did not stop in as we were not willing to sit in the car any longer by this point.

For those who prefer home brewed beer, check out the award winning Publick House in Southampton. This pub-like establishment serves seasonal beers and never maintains a complete beer list as it’s constantly changing with more than 30 beers brewed on-site.  We found the best value to be the beer flights that consist of ample tastings of 8 different beers for just a little over $1 each.

We’re not beach people so aside from driving and snapping a picture of a seemingly very crowded private beach, I don’t have any recommendations other than the obvious, get there early (and wear sun screen)!

If you want to enjoy the water without the crowd, check out the East Hampton Point restaurant overlooking the marina and SUP board adventurers. Yacht watching will not disappoint! The crabcake main course was delicious but not very filling. The wine list made up for it!

Nick & Toni’s is no site for sore eyes but it remains a hot spot for celebs and locals for their weekly changing Italian menu and new pastry chef.  As we didn’t stick around for dinner, we sadly missed this recommendation.

For those wanting to stalk sight-see celebrities, check out this Celebrity Homes in the Hamptons listing. Don’t think we didn’t get out of town without seeing Sir Paul McCartney’s humble digs 🙂

Overall, we were a little disappointed in The Hamptons. There aren’t historical sites to see (after all, this isn’t a tourist town) and the foodie scene lacks much to be desired given the amount of money pouring into these towns.  However, we could clearly see how owning homes in the vicinity, popping bottles under the sun of your own private pool or ocean front property, and having a private chef take care of  your every hunger pang could easily be nothing short of amazing.

For our budget and entertainment, we prefer Newport, RI any day!

Other food recommendations we found while browsing through blogs:

Sag Harbor 
Harlost East – The restaurateur, Richie Notar, is most known for opening the famous Nobu in NYC.  Harlow East is situated on the water and offers the same raw bar and popular items from the NYC hot spot plus a few new seafood treats using the local produce.

East Hampton
Sienna Restaurant & Ultralounge – I think the name speaks for itself: unce-unce-unce with aside of sea-bass and steak tartare. Sundays in July, get your boozy brunch.

Southampton
Delmonico’s

The Plaza Café – “trendy but relaxed atmosphere…unique renderings of tuna tartare…and lobster ravioli…indulge in the strawberry-rhubarb crisp”

East Quogue
Station – farm-to-table style with outdoor seating. Bonus: backgammon!

Cheers!