I think the Hamptons (and Suffolk county generally including the North Fork) are very nice for a localish gateway, but I would not pick that over a quintessential preppy NE vacation on MV or Nantucket if coming from a different part of the country.

MV

They are different vibes. They all have wealth in different ways and so many of these so called "comparisons" are just off. The Hamptons is more for New Yorkers who are used to Manhattan all the time and get out to nature, exclusive beaches, towns with upscale restaurants, etc. You often have to drive to the beach and they don't mind. It has an unapologetic happening "scene" at night. They are more focused on being luxurious and glamorous versus "charming". People take themselves seriously.

Nantucket/ MV has the classic New England vibe- more family oriented, historical buildings and hydrangeas, bike rides to get ice cream in your sear suckered clothing. Nantucket has one town versus MV has several with different personalities. Edgartown is the preppiest and most like Nantucket. MV has older homes, lots of diversity and some crunchy/hippie vibes in some areas. Don't go for a glam scene for either- there isn't one especially in MV.
Lots of daytime activities- beaches, biking, boating but I wouldn't go alone or think to meet anyone

We have a house in the Hamptons and I love it there, but we live in NYC and that choice was driven by the location and convenience of getting back and forth. If I were renting a place and staying out there for a week or more for a summer vacation, I'd choose MV. I think it's so lovely there.

Anonymous wrote:Different take: Hamptons incredibly beautiful if you get off the beaten path and out of the towns. Serious natural beauty with incredible state parks and nature preserves on the way to Montauk and through the little islands up to the North Fork. Some of the people can be intense, but I find it very relaxing and beautiful in Hamptons.

Also, beaches better (actual gorgeous sandy beaches) and much warmer water for swimming.

There is a reason the Hamptons are so expensive. Everything is nice there and easy. You can't go to the beaches unless you have a season pass which you need to own a house to get one or you pay an expensive day pass for your car. This means the beaches are not crowed at all and they have a very nice, clean, upscale vibe. People are not smoking etc.. The lawns are all manicured and beautiful. Streets are clean and full of shops and restaurants and cafes. Very different vibe than MV or Nantucket and have been to all. I prefer Hamptons personally but it is much more expsensive as they do not have many hotels there purposely so renting a house is very expensive - $20,000 minimum per week.