A weekend in the Hamptons  

I recently got this travel diary from my friend, Richard Joseph, who took a weekend trip to a very exclusive area-  the Hamptons.  Was he able to visit on a budget?  Read on for his impressions of this lovely area. – Heidi.

I’ve heard the phrase “weekending in the Hamptons”, but it was a phrase always in reference to the rich and/or famous. My son and I attempted to do it on the relatively cheap and here’s what happened.
Hamptons Home

Boarded the Long Island railroad for the two hour plus trip from New York City eastward about 100 miles from Manhattan. The ticket was $40 round trip, not a bad price. At Jamaica (not the Caribbean island) in Queens we switched from an electric to diesel powered double decker. The heavy morning thunderstorm gradually gave way to overcast as we sped along the south fork Montauk route of Long Island. There are several Hamptons along the line including West Hampton, Hampton Bays, Southampton, and East Hampton. We chose Southhampton to disembark for two good reasons. Number one it had the only Enterprise Car Rental open on Sunday for return and it was fairly near the one hotel we could find that would squeeze us in on one day’s notice.
Hamptons Windmill

The $100 for a day’s car rental seemed steep, but even Relay Rides was sold out. Getting around the Hamptons without a car is doable, but not easy. Ferrari appears to be the car of choice in the Hamptons, we got a Toyota Camry. The skies were clearing so we asked where would be a nice place to have lunch overlooking a harbor. Without hesitation we were sent by the car rental clerk through the backroads woods to Sag Harbor. A windmill (like many that dot the area built from 1795-1820) stood guard over the port there filled with yachts with Grand Cayman registrations . A little seafood restaurant overlooked the boats so we dined there on chowder and shrimp rolls.

Saturday later afternoon

My research had warned us of a danger far more likely than sharks on this exclusive part of Long Island, expensive parking tickets. If you don’t have a resident permit it’s forbidden to leave your car at many, if not most, of the beaches. A local man kindly told us we might get away with it at Sami’s beach. I see why he said that, finding this beach was not easy. After getting lost a couple times (yes we even had a gps) we arrived at Sami’s. It was a very nice long strip of sand facing into the bay as opposed to the Atlantic side a few miles away. Aside from a few sand flies it was the perfect getaway for my son who badly wanted to get out of Manhattan after a month of living there.

Hamptons BeachEven later Saturday afternoon

We each held our breath as we returned to our car. We discovered we had survived the few hours without a $150 ticket. Next stop, to find out what kind of hotel we ended up with booking only a day in advance. The answer is you get what you deserve for waiting so long. For $400 a night (tax included) I was not optimistic when I saw the peeling paint on the room door. It opened to a kitchenette with stove out of the past, the electric heaters on the floorboards were rusty, the screen on our porch was torn.The owner of the hotel couldn’t have been nicer. Believe me we did not want to spend this much for a night, but that’s pretty much the going rate for the low end. We even tried Air BNB, but it was sold out. We found our place through the local chamber of commerce.

Hamptons ParkingSaturday evening

With no firm idea in mind we headed east towards the end of Long Island. What starts in Queens ends in Montauk. We passed through the “charming” village of East Hampton where we rolled down our windows to see if we could smell all the money. Then along the two way highway through Amagansett and eventually into Montauk. It’s immediately apparent that Montauk is not a “Hampton”. Montauk has entirely different flavor, this is a fishing town and it’s also a town for young people to play. Lately it has gotten a lot of bad press for wild nights. By dumb luck we took a turn that led us to Gosman’s Restaurant. There since the late 1940s, it overooks the harbor with working fishing boats. The food came right from where we were looking. For $68 we had a huge dinner for two: tasty mussels in broth, a delicious large lobster (thankfully with the shell cut), baked potato and flavorful corn on the cob.

Sunday morning

There are few chain stores in the Hamptons, which was a nice change, but we managed to did manage to find a Starbucks. After downing our mandatory coffee we headed to Wainscott beach. Our hotel provided a guest parking pass so we felt we could relax there without worrying about a ticket. As we got close to the waterfront the sky went from clear blue to a thick fog that hung over the beach giving it an eerie appearance. It would have been easy to stay there all day, it was perfect with beautiful fine sand. Unfortunately we had to return our rental car so after a couple hours we found our way back to Southhampton. The drive reminded me of two words I had always heard in connection with the Hamptons , “expensive” and “traffic”, both turned out to be true. The Montauk Highway (route 27) is two lanes with stoplights that back traffic up for miles. All the Ferrari’s were stuck doing 5mph. Like many of the villages in Southhampton the beautiful homes here are guarded by high hedges to keep the envious from getting too much of a glimpse. Perhaps if they saw too much they might want to be rich too.

Sunday afternoon

We asked the Enterprise driver if he might drop us at Cooper’s Beach. He said he would..(more on that in a moment). We arrived at the beach, luggage in tow, to spend our last few hours on the same sand as multimillionaires (the billionaires have their own beaches here). Just behind the safety of the dunes are more than modest beach houses. Most commonly these houses are gray and quite large. The coastal fog had cleared and the giant waves on the Atlantic provided nice relief from the hot sun. After whiling away the hours doing nothing we called for a taxi. We told the driver we were at Cooper’s Beach. When no taxi showed up we called and were asked to describe where we were located. This wasn’t Cooper’s Beach. Apparently our Enterprise driver took us to a different beach without telling us. Well, the taxi eventually found us and got us to the Long Island Railroad station just in time. It was 4:10pm, but the 3:34 was just arriving. The ride back to the city went quickly making me wonder why people drive.


We got our weekend in the Hamptons. It was wonderful, but we did not succeed in doing it on the cheap. It’s a great place to go, but be sure to bring money…lots.

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