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First time to the Hamptons : need general advice

new york, ny
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First time to the Hamptons : need general advice

Dear Fellow Travelers,

My husband and I have heard great things about the Hamptons and Montauk and would like to head out there for a couple of days. We'd love to visit some of the vineyards and just relax. Should we stay out there for a day or two or will a day trip suffice? If we stay out there, what area/town is best? Lastly, we heard there is a ferry we can take there from Connecticut instead of drive there? Any advice on this?

Thanks!!!

Buffalo
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162 posts
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1. Re: First time to the Hamptons : need general advice

I don't think you could really see the Hampons in a day trip. The Hamptons span from Westhampton to Montuak. There is and hour and a half drive in between those two towns.

There is a ferry on the North Fork that goes to CT. I don't know much about it, I took it once about 15 years ago and don't remember the details. The Hamptons are on the South Fork of Long Island, so even if you took the ferry, you'd still have a little drive.

I love Montauk and if you want to relax that's a good place to do it. If you can go on a Mon to Thursday night you will find cheaper rates at hotels or motels.

New York
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126 posts
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2. Re: First time to the Hamptons : need general advice

Definitely plan on a long weekend at least. The area has so much to offer and can be so relaxing it would be a shame to rush. The South fork has great beachs, shopping, restaurants, farm stands. The North Fork has many vineyards, farms, etc. If you are looking to see it all (?) Southampton might be good for you. It is a good central point for the South Fork and you can go west and east easily. Sag Harbor is also a great spot to stay, and has a lot to offer on it's own. As for staying on the North Fork, I'm am not that familiar with options there.There are two ferries, the one to Pt. Jefferson and also one to Orient Point. The Pt. Jefferson ferry would be good for most points, Orient would be good if you plan on staying on the North Fork. If you want advise regarding specific towns or accomodation just post your options and I will try to answer them.

Riverhead, New York
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3. Re: First time to the Hamptons : need general advice

Coco;

a day trip would leave you wishing you stayed longer. BEWARE, the traffic is insane at this time of year so patience is a must.

I see you are from NYC...why would you drive to CT and take the ferry over? The crossing itself is about 1½ hours and is pricey with a vehicle.

This is what I would do:

Drive yourself out and work your way east. I'd stop first at Westhampton Beach and have lunch on Main St. - Funcho's is a fun little mexican joint, not expensive with outdoor tables - great people watching!

Afterward hit the beach via Dune Road...not being a resident of the area, the only beach you could go to west of Hampton Bays is Westhampton – Pikes Beach (Dune Road, West of Jessup Lane) $15 per day. Afterward head east on Dune Rd. to to Hampton Bays, along the way you'll see simple beach houses to extravagant mansions and architectural one-of-a-kinds. The road ends in Hampton Bays, so you'll need to take the bridge back to the "mainland"

Head further east to the Village of Southampton to spend the night. There are some nice places...just keep in mind that it is high season and may be pricey. Lots to explore in Southampton - spend the whole day here if you can. Parrish Art Museum is good and the grounds have lots of sculptures and cool park benches to eat a bag lunch. Maybe head to one of the great beaches or just drive down to the Inlet. Oh, did I mention shopping? Shopping...yeah, shopping!

Heading further east you'll pass through Water Mill, Bridgehampton and the vineyards. Too many wineries to list, just stop in, taste, tour and buy! ...then on in to East Hampton Village. This is another great place to stroll Main St , check out Guild Hall to see what might be playing when you are in Town - you never know what celeb may be poppin' in... ... for the eveing drive further east until you are in Montauk. Check in to your hotel and spend the following day checking out the lighthouse, the beaches and the "Birthplace of the American Cowboy" Deep Hollow Ranch http://www.deephollowranch.com/ for some great horseback riding. I'd end up having dinner at Gosman's Dock http://www.gosmans.com/ and probably head back home to my own pillow that night!

But, that's just my opinion! Enjoy!

new york, ny
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4. Re: First time to the Hamptons : need general advice

Thanks so much for your advice!

So, now I need some more...

We are currently staying in Holtsville and plan to spend day in the Hamptons area tomorrow. We'd like to spend the morning at the beach, have some lunch, drive out to a winery or two while enjoying the drive through some towns and have dinner somewhere with great food. That being said, any suggestions on what beach to stop at, what towns to drive through, what winery to visit and where to have dinner before heading back?

Thanks so much!!!!

Buffalo
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5. Re: First time to the Hamptons : need general advice

I don't know much about wineries but if you drive down Montauk Highway from Westhampton, you'll drive straight through the centers of all the Hamptons. From WHB to Montauk is 1.5 hours.

Stop by and pick up a Dan's Papers and a Southampton Press from a local store to see which restaurants people are buzzing about.

Most beaches require a beach permit. There is one in WHB that doesn't, but I don't remember the name of it. Drive along Dune Road from Westhampton Beach to Hampton Bays to rubberneck at all the mansions. You'll pass all the beaches in WHB, Quogue, East Quogue and Hampton Bays that way. You could ask someone which one you can pay to park at.

You might start in WHB, travel east along Dune Road until it ends in Hampton Bays and then get on Montauk Hwy for the rest of the drive, that way you see some beaches and the quaint villages.

Have fun!

6. Re: First time to the Hamptons : need general advice

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