My husband and I are looking for a quick get-a-way from the Boston area. We thought the Long Island area might be nice, but I can't get a sense of the different towns.

We don't want glitz, glamour and attitude, just a quaint, charming village with shops and restaurants we can walk to. (Something similar to Nantucket Island, MA). We will be going in mid-October, so beach doesn't really matter.

How do Greenport, Easthampton, Southampton and Montauk compare?

While many of these towns are awash in glitz and attitude all summer, I think you would find them very enjoyable in mid-October after the summer crowds have departed. Southampton and East Hampton are both lovely villages with a variety of shops and restaurants. Montauk would be much more remote--and I'm not sure how much of a village there is. I don't know Greenport.

You might also really like Sag Harbor, which is a smaller village, but probably wins the quaintness contest. It's further away from the ocean, but it's on the bay and it's still convenient to other towns.

I think you'll have a great time, it's really a beautiful area and very enjoyable in October.

David is right about Sag Harbor and you also might take a look at Shelter Island.

Except for salt air and some similarities in architecture, Nantucket and the East End are difficult to compare.

As far as comparisons:
Easthampton/Southhampton have much in common though Easthampton is more toned down. Montauk is entirely different - with a commerical and private fishing industry, that the others don't have, you'll find a wider range of folks living/going there. The ocean and harbor areas bear no resemblance to their western "Hampton" neighbors.

All in all, you might find Sag Harbor best fits your requirements and would be a good base for a long weekend.

What are the tolls like from Manhattan to the Hamptons? I'm driving there next month and want to know the best/cheapest route?

Debbie-
South & East Hampton are great choices. Go online and select a nice B&B in either locale and you will be satisfied.
Question for you....can you recommend a couple of good hotels (4 or 5 star) in Boston (Commons, Beacon Hill area)? Thanks

I have found that Montauk , which definitely has a town center(village) is the most laid back of the Hamptons.Speaking of attitude-East and South are way too self conscious,lines to get into every eatery,movie,gallery.Very annoying,might as well be in the city.
Whereas Montauk IS still a fishing village,so the locals are more down to earth.
Greenport is great! not on the beach though,but the bay.Interesting old homes,farms,if you would like to fall in love with a little beach town,go to Orient Point! OMG,dripping with charm.
That area is full of great eating places, good ones right on the water also.Have fun!

I love Sag Harbor!! They have a very nice hotel,the American Hotel.There is a good restaurant there and down the street are a few really good ones.The movie theatre shows first run foreign films and there is some fun shopping and antiquing.There is a winery close by also.Kate

Debbie, Suggestion # 1. Take the ferry across the sound from New London to Greenport. It's wise to make reservations. Then take the smaller ferries to cross Shelter Island and onto Sag Harbor. It's a nice trip and you avoid driving all the way into NYC and then out east again in all the LI traffic. Staying in Amaganset would have you centrally located between Montauk, Montauk Point, and the Hamptons.

Allyson
Re: tolls
Use the 59th St, Brooklyn or Williamsburg Bridges to avoid any toll out of Manhattan.

Once on LI, it's toll free to Montauk.

What about Bridgehampton? What's that like?

Debbie,
Haven't been to Bridgehampton since they closed to auto race course - many moons ago.

Here's a link:
http://www.hamptonstravelguide.com/Bridgehampton.htm

Bridgehampton is one of the first that you come to,East Hampton being the farthest out on the tip of the island.
It is great for restaurants, and shopping, a lot of people are buying homes there. They are all nice beach towns, just very busy NY social scene going on all the time, which if you are a NYer,it can get tiresome.
Their beaches are also not as nice as farther out.
My husband reminded me that the last time we were in Greenport it was a touch "seedy" so you might want to rethink that.
I second the recommendation for Shelter Island or Sag Harbor.Both are beautiful,and charming,and of course,have lovely beaches.

When I say East Hampton being the farthest out on the tip-meaning the farthest Hampton ...past EH there is Amagansett and then Montauk.

My husband and I are considering a trip to the Hamptons area in July or August. We love great beaches. If you are not staying in a house on the beach are there still many beach areas to go to? We typically go to islands or South Beach so we would still like the blue water effect.

Are the hotels pricey or is a B&B a better bet. What about hotels on the beach?

We would be flying from Atlanta. Where should we fly into? We would probably rent a car to better see the area while visiting there.

Theresa

Big problem here is that most hotels /motels in the Hamptons are booked for the summer already.
Everything is expensive.

Greenport has really cleaned up its act in the past few years. There are many new boutiques, galleries, and restaurants. My parents still live in Mattituck (about 10-15 minutes from Greenport) so I visit there frequently and lived there until 1995. Greenport is mostly a laid-back fishing village but an influx of people from NYC, Nassau County and the South Fork has brought about a revitalization. That being said, the beaches on the South Fork are much nicer and there are certainly more things to do.

When in Sag, you must dine at Beacon. The view is superb. Zagats give it a nice rating. I believe they require one to be in black to enter.

fanny,that will be just fine with me what is the name of the diner that was taken over and now serves great food> right next to the movie theatre?

Theresa,
EH is right about finding accommodations at this late date. However, I've been able to get July/Aug. space at almost the last minute along the ocean beach hotels from Ammagansett->Montauk. They do get cancellations. Do a google search on montuak or hamptons, ny and you'll find several good area sites on the 1st page of results

Re: Flying. Delta (ASA) has service from ATL into Islip McArthur (ISP) 2-3 times a day. Islip is ~45 minutes from Southampton unless you arrive on a Friday anytime after 2PM, then the trip is 8 days ;-)
hth,

Why NYgirl, if I recall correctly, that place, since closed, was called the French Kiss. Are you thinking of the place with the sleeping caribu stain glass windows? They were so exciting, it just made one want to jump out of their BVDs. Sag is a special destination still.