I am attempting to organise my holiday to New York next year and would like to include a night or two on Long Island in my trip.

I am thinking that I could either hire a car in New York & use the car ferry from Orient to continue on our holiday to Maine before returning to New York or get the train/jinty & then ferry to New London from where I hire a car for the rest of the trip.
I think the train or jinty would be more enjoyable and preferable but then there would be the problem of getting around the Hamptons & arranging car hire at New London/Groton plus drop off surcharges on returning to New York.

Hiring a car in New York gives the freedom to explore but then there is the problem of booking in advance the car ferry crossing – always expecting delays I would be worried about booking a fixed departure time.

I would be interested to hear any views or experiences on this.

You don't say what exactly you want to see on Long Island. You mention the Hamptons but it depends on what you plan on doing as to whether you can manage without a car. That said, there are car rental places in the Hamptons if you want to use public transport to get there and just rent a car while you're visiting. Enterprise has a location in East Hampton and Southampton and there's a Hertz as well. They're pricey in summer though. I don't know whether they'd offer an option for drop off elsewhere if you wanted to continue on in that car.

I also wonder if making stops on the way to Maine is the idea of the trip. If not, have you considered other options besides driving the whole way? It's a very long trip. With gas prices and car rental prices, you might be better flying. You can fly from JFK or LGA to Portland, Me.

I think booking the ferry in advance should be the least of your worries. If you miss a ferry they will give you standby priority to get on the next one. If you arrive early for the ferry before and they have room, they'll let you on. I'd just try to plan to do the ferry during the week vs. a busy time on a weekend if this is in season.

Would you care to share the itinerary for the whole trip?

I was planning the trip for this year but plans went awry.
Following on from my last 2 trips we arrive New York, spend a week there & then tour New England & then head back to New York for 2 or 3 nights before returning to the UK.
My plans for this trip were New York for a week, then off to Sturbridge 1 night, Kennebunkport 2 nights, Camden 2 nights, North Conway 1 night, Burlington 2 nights, Greenfield 1 night & back to New York.
I have wanted to go out to Long Island but travelling back to New York to go out to New England seemed too much of an effort. Taking the ferry from Orient makes it a possibility that I want to consider. I would stay between Montauk & Orient if the ferry option was chosen. Then I would go from New York to Long Island & then continue on to Sturbridge.
The car would be hired from New York or New London. I would use train or bus or taxi to get around Long Islands if I don't have a car.

you'd do better with a car on Long Island. it's much easier to get around and see things.

and to echo what mclaurie had said..it's not hard to get on a later ferry if you miss yours. Especially if you do it on a weekday. I once missed the ferry from New London on a very busy Saturday morning in the summer and I did have to wait for 2 hours for space for my car. but that was probably the worst case possibility. Also, if you book on a weekday, you are unlikely to encounter a lot of traffic delay out around ORient. You should have no trouble making it on time.

Don't now if you've looked at a map of LI - but Montauk is the end of the South Fork and Orient is the North Fork - with the Great South Bay in between. To get from one to another can be time-consuming (esp in season) since you have to backtrack quite a way to switch forks.

Agree that to really do/see much in the Hamptons yuo need a car. (Jitney is fine for people staying in a beach house for week and not moving around - but is very hard to see much without a car.)

well, Shelter Island is between

Really you should decide which side interests you more, and stay there but not too far out towards the point. So if you stay in the Hamptons somewhere not to far east, you can relatively easily go around to visit the wineries on the North Fork. Its not too terrible. Well, except for summer weekends when the traffic can get pretty awful.

oh, and I should mention...your New England itinerary looks awfully busy to me. too much driving around! there's little time to relax and see things in that trip.
(then again, I'm always saying that because I hate 1-night stopovers. it works for other people though. None of the driving legs are overly long so maybe its okay)

I don't agree with your plan (and I do agree with comments from nytraveler and china cat). I think you should consider these options

1)heading north from NYC toward Maine. Make fewer stops. On the way back, use the ferries and spend the last 2-3 days on Long Island instead of heading back to the city again. Drop the car at JFK.

2) Do 2 days in the Hamptons from NYC, not as part of your road trip.

3) Drop Long Island from the trip altogether.

You do need to examine a map of Long Island. The end of the island is like a fishtail with Montauk at the end of the south fork (bottom of the tail) and Orient Point the end of the north fork (top of the tail). If you want to see the Hamptons/Montauk, to get to/from Orient Point, you'd take 2 ferries passing through Shelter Island. The ferry trips are short and don't require pre booking. There are passenger ferries from Montauk to Block Island, but that starts to get too complicated.

MCLaurie, the drive from someplace like Southhampton to Orient is maybe 90 minutes,even going around through Riverhead. MUCH shorter than trying to take the ferries across. that's why I suggested he stay someplace a little closer to Riverhead. Then can spend a day driving out to Montauk, and another day driving to the North Fork. Even Montauk to Orient takes about 2 hours.

Its been a long time since I took the ferries across, but my recollection is that while the ferries were relatively short, they didn't run all that often, and you had to drive across Shelter Island. It was an interesting trip, but took over 2 hours when you added in the drive times, and the waiting and boarding time.

But John should definitely take a look at a map, and decide what he wants to do/see on Long Island and then make a decision about where best to stay. I just wanted to clarify the options(hope I haven't muddied the waters!).

There is more dining, shopping (of the boutique and gallery variety) and better ocean beaches on the South Fork. Its quieter, and more wineries, antique shopping and less crowded LI Sound beaches on the North Fork. At least, that's my feeling in a nutshell.

John has still not told us when he's planning this trip, has he? Timing is everything. The ferry from Sag Harbor to Shelter Island is very frequent and very fast. The ferry between Shelter Island and Greenport can a long wait and tiresome. Agree that if you stay in Southampton it may make more sense to just drive to Orient Point, but from any place east of there, it begs the question. I still think it would be better to do the Hamptons stop at the end of the trip on the way to JFK instead of heading back to NYC.

I agree with your last point for certain. I think your routing makes more sense. Maybe reverse the loop, go from NY up to Vermont, then across NH to Maine, down through Massachusetts to the ferry and across to Long Island.

and also, it does depend on when.

Our holiday would be the end of July to start of August.
My wife has wanted to go to Camden and wants to go to Vermont again, so based on other trip reports I put together my schedule. I realise there is a lot of travelling which is why I introduced the 1 night stopovers to break up the trip.

Last year I based us in Hyannis & as the driver I enjoyed that more than the previous years drive - Mystic, Falmouth, Boston, Concord NH, Hanover, Lee - but everyone else preferred the first trip.

The Long Island section, I was leaning towards stopping around Shelter Island. The Barefoot contessa is responsible for our diversion to Long Island.

The last 2 nights have to be spent in New York. I envisage New York from around 23/7 for a week which puts Long Island a Thursday & Friday stay. The rest of the trip will follow on from that. I was a little uncertain over using the ferry with a car or getting the hire car in New London.

Amazing that Ina Garten is responsible for your wanting to go to Long Island. I hope you realize her shop no longer exists. Staying on Shelter Island could be fun. Sunset Beach is a lovely spot although pricey for what it is. I think it's pointless to be without a car on Long Island and it sounds like there are more than 2 of you. That starts to get very pricey for the Jitney and the train doesn't run that frequently.

You may have minimum stay requirements on accomodations in the Hamptons/Shelter Island at that time of year, especially on a weekend night (ie Thur/Fri may not be possible). I would try to avoid Long Island travel on a weekend.

The reruns of her show are on every night & my wife & daughter watch it avidly. They like the drives around town & want to see the area. Also the area was painted by Hopper & that is also another reason to go.

Now that I am looking into the area I noticed that 2 night stays are required in most places. I also see there is a ferry from Port Jefferson. This will give me more scope to choose somewhere to stay.

Port Jeff ferry is fine - but not a place to see the Hamptons rom.

In the summer you will find it very difficult to get a Friday night without also taking the Saturday. (Since most people want both if they give you Fri they might well not be able to sell Sat.)