NYC-Hamptons
 

Need help from Fodorites with our itinerary. Arriving NYC and spending two nights in the Hamptons first and would like your opinion if it's better to drive to Boston or Philly from the the hamptons? We're planning on staying at either place for only 3 nights so hopefully we can see the main tourist attractions of either city. Afterwards drive back to NYC and stay for 3 nights. We'll be going the first week of Oct if this helps any.

Neither is particularly convenient to the Hamptons.

To reach Boston from the Hamptons you could head to the north shore to Orient Point and ferry across Long Island Sound to New London, Connecticut. This would make for a more interesting drive and eliminate the need to return to NYC to head to Boston.

I agree on the ferry to CT and then drive to Boston - this makes the most sense.

The ferry but check to see if reservations are neeed.

The Hamptons in Oct. will be quiet. Not sure what you're expecting to see. You can take several ferries starting in Sag Harbor to get to Ct. and head toward Boston. It's not a shorter trip but perhaps more interesting. But the Hamptons is an inconvenient jump off point for your trip. I'd nix it and head directly to Boston by plane and then do a daytrip to Phil. from NYC.

There is no point in staying in the Hamptons - at the far end of Long Island to see either Boston or Philly. The only reason to go to the Hamptons is to stay there and do beachy things.

If you want to see NYC, Boston and Philly you should just stay in the city and take a train to either Philly (doable as a day trip) or Boston (too far for a day trip - will take 8 hours back and forth).

Why go 100 miles out of your way to the Hamptons if you don;t want to see THEM?

Perhaps looking at a MAP would help you visualize the situation.

The Cross Sound Ferry will take you from Orient Point on the North Fork of Long Island to New London CT from which you will follow 95 to Boston via 93(?). You can get easily from the Hamptons to Orient Point. You will need a reservation for the ferry or you might literally be left at the dock. A # for them is 631 323 2525. Look on your recently acquired map and it will make more sense.

Thank you all so much for your replies. I guess it seems a little bit cumbersome to go to the hamptons but our intention was to have a little "getaway" from the city scene and just relax for a few days.
Nytraveler-i think your suggestion makes more sense by taking the train to philly(possibly 1-2 day trip) and boston for 3 days.

Why don't you 'relax' in Newport on the way to Boston? I've been there out of season and it was great. Nice hotels or charming inns, good restaurants, tour a couple of mansions, walk cliff walk, drive ocean drive, etc.

We've decided just to nix boston this time around. So from JFK, we'll either drive or take the LIRR to Easthampton and stay for 2 nights. Then head to philly for 2-3 nights and return to Manhattan for the last 3 nights. Is this doable?

Doable but I think a bad decision.
1) Boston is more interesting than Philadelphia, esp. for 2-3 days. As I said, Phil. is an easy daytrip from NYC.
2) Phil is a cumbersome trip from East Hampton.

I liked Centralparkgirl's idea of heading to Newport, RI from JFK on the way to Boston as a relaxing spot. OR, if you have your hearts set on East Hampton, I'd then head to Boston by ferry and nix Phil.

I share the concerns of everyone here about your Hamptons jaunt. I'm not really understanding why you want to go to the Hamptons in October, when most of the restaurants and shops will be closed or at least very quiet and when the beach will be too cold to enjoy.

It's certainly do-able to get to the Hamptons on arrival at JFK (take the Airtrain to Jamaica, and then hop on a train for the 2- to 3-hour trip). However, I'd have picked a different destination to relax for a few days. I really like the idea of Newport, but that would require driving, and you may not want to do that. Would you ever consider Atlantic City?

Plan on 6 hours of travel time to get to Philadelphia from the Hamptons. It's about 2 to 3 hours back to NYC, then you have to get on either Amtrak or NJ Transit/SEPTA (I'd recommend the former if you have a lot of luggage because you'd have to change trains a 3rd time if you were to take NJ Transit to Trenton). It will cost about double to triple to take Amtrak over NJ Transit/SEPTA, but it's more convenient and faster, which I think is important if you are coming all the way from the Hamptons.

I think Philadelphia is worth at least 2 nights. There's much more to see and do than you could manage on a day-trip, though it's certainly possible. If you don't go to Boston, would you consider a jaunt out to Lancaster county from Philadealphia? It's relatively short distance by car, and you could then see a bit of the countryside. Plus, it's not quite as busy in October as in the summer.

Where are you from that you need "a little 'getaway' from the city scene and just relax for a few days'? Why are you going to a city if you want to relax from it?

The Hamptons are not easily doable without a car. You can take the LIRR to get there - but one there you need a car for easy travel around towns, to the next town - to see Montauk or head for any of the beaches - which can still be pleasant to explore - although obviously not swimming weather in October.

But do be prepared for many seasonal places to be closed - esp during the week.