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Vacationing in the Hamptons late September?

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Vacationing in the Hamptons late September?

So I am trying to determine a vacation spot to take my wife for her birthday. My funds are somewhat limited. I know that normally the Hamptons and limited funds do not go well together but I am thinking about taking her there the last week in September, which they say is off peak time and hotel prices are not always as bad, supposedly. Also we live in CT so we could easily drive there and that would save the cost of a plane flight.

One of my main concerns is that by the time the end of September roles around, the weather can be a bit iffy, it may still be warm but it could also be cold since we are in the fall time. Also I am assuming the activity and business dies out once the summer is past and my wife may be bored with that. Plus the hotels may not be that inexpensive anyway.

I have not started looking at hotels yet but would be grateful for any tips or advice anyone may have about knowledge or experience with the area.

Paul

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1. Re: Vacationing in the Hamptons late September?

It may not be swimming weather but it will still be nice and unlikely cold. But with limited budget, I don't think

the area will be cheap enough and most activities apart from beach involve spending money. What kinds of things does your wife enjoy?

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2. Re: Vacationing in the Hamptons late September?

Hi Nywhiz, I note that you reply a lot and seem to have plenty of knowledge on Long Island. My husband and I will be travelling from Ireland to Washington for 3 nights in September. Our intention then, is to fly to JFK and spend 3 nights somewhere relaxing but still plenty to do (without a car) and finish with 3 nights in Manhattan. I was thinking of East Long Island - Montauk, East Hampton, Sag Harbour - somewhere big enough to not get bored walking around for 3 days. We will happily do any excursions available like vineyards or boat trips. I looked at Fire Island but it seems to be really quietening down by then. Also we don't want to spend a fortune on accommodation - I have been looking at Airbnb. I wondered would be better off going to Connecticut - somewhere along a train line - like New Haven? Any advice would be great.

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3. Re: Vacationing in the Hamptons late September?

Getting around the Hamptons, esp off season, without a car can be very difficult. There is practically no local transit except taxis. And I think you may be underestimating the size of the area - how many towns there are and how far apart they are - esp if you want to go to the North Fork to visit any of the wineries.

Most things will be still be open late Sept, esp on weekends - and while prices will be lower don;t expect any bargains.

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4. Re: Vacationing in the Hamptons late September?

I live on Long Island and completely agree that a car is a must. The Hamptons is really little towns that are each several miles apart.

Late September is actually quite a busy time on eastern Long Island because it is harvest time on the North Fork (where most of the wineries are) and also pumpkin picking time which has turned the farmers' businesses into a major event. People shop for pumpkins, fall flowers & decorations etc and kids love the corn mazes.

For the OP, I might suggest that you look at the North Fork wineries for your wife's birthday weekend. You could take the ferry from New London CT to Orient NY and stay at a B&B, perhaps near Greenport. That's a lovely town with plenty of shops, restaurants etc to keep you busy when you want to. Many wineries are just a short drive from there. You could also take a wine tour, with someone else driving.

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Dublin
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5. Re: Vacationing in the Hamptons late September?

Thank you, that's very helpful.

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6. Re: Vacationing in the Hamptons late September?

There are plenty of relaxing places near Washington although not sure how easy they are without a car. Most places that are countrified don't have much public transport. Cold Spring is one place easily accessed by Metro North train from NYC. Btw, you may want to think about the train from Washington to NYC, esp. if you,re heading somewhere else by train. There,s no benefit to arriving to JFK if you,re not renting a car and train goes city center to city center.

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7. Re: Vacationing in the Hamptons late September?

Hi all,

My husband and I are also scouting a trip to the Hamptons in the last weekend of September. I see the advice above, but car rental is expensive. If you had to take the train from NYC, which town would you consider the best to stop and stay and get that "Hamptons experience?" The most walkable village for 3 days of general relaxation?

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8. Re: Vacationing in the Hamptons late September?

I think you would be bored to death in any one village for 3 days. They each have things to see/do but by late Sept they may be off summer schedules - so small museums or old houses may be open fewer hours or fewer days. I know people don;t seem to get it - but to get around easily you really need a car. (Have been going there every summer since I was a child and you have ALWAYS needed a car to get to restaurants, the beach and many of the sights.)

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9. Re: Vacationing in the Hamptons late September?

Thanks!

10. Re: Vacationing in the Hamptons late September?

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