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Sounds fabulous!

You're ok to enter for upto 90 days on the esta.

We've done several road trips to various parts of states but for maximum 18 days.

For a starting point I used to get brochures with escorted tours eg Titan tours and also virgin have fly drive holidays.

We've done over various trips - california, new england, deep south, virginia, tenessee, washington DC, new york, memphis, nashville, vegas.

With that length of time i'd be tempted with coast to coast or route 66.

Once we'd decided on our area and approx route i'd get a guidebook like fodors and plan away. Unless we wanted to stay somewhere special like a b&b we just used to book accomodation each night.
 
I know you said you didn't plan to drive even though you mentioned it being a road trip, but I figured I'd throw this out there anyhow :)

Him indoors is enamored with the idea of doing Route 66 on a motorbike (I think it may be a midlife crisis :lmao: ) and I've been charged with researching it for him in the hopes of doing it sometime in the next 3 years or so.

During my research I found this site which is pretty cool. Road maps, photo's, forums for questions etc, anything to do with Route 66 basically. I wasn't particularly interested in it before (and I still have no intention on getting my butt on the back of a bike, LOL) but after poking around this site I must admit, it does look really cool.

Route 66 runs from Chicago to LA...so you could even finish it off with a trip to DL! ;)

Anyhow, figured it might be interesting for you, and even if you don't do an actual road trip it might inspire some other ideas :)
 
we looked at a few road trips ideas and one of the companies we found was american sky which offers various pre planned road trips and they are all various lengths.

The other option is get a really good us guide book and then book the flights and car hire and just wing it, which might be risky but a whole lot of fun.
 

I done a road trip a few years ago only for 25 nights though we flew into Jfk stayed in NYC, Pennsylvania, West virginia,Kentucky, Tennessee, Georgia, Florida, South carolina, North carolina, Virginia, washington DC, Delaware, Maryland and New jersey we drove staying in hotels and and a RV for 5 of the nights its was one of the best trips I ever done loved seeing so much. I planned it all myself and picked hotels beside sights to see I used Trip Advisor for details on hotels and areas :)
 
You lucky thing I would love to explore America like that.
Im confused though as you called it a road trip but then say you are planning to fly from place to place - a road trip to me is driving from place to place.

If you are intending to just fly I would imagine it would be easier to organise in some ways.
You probably need to make a list of where you want to visit - major places then decide roughly how long you want to spend at each (eg NY 1 week), then research that area and see if there are any trips (day or overnighters ) you can do from that area which then might mean adjusting your number of days in that area.
Once youve got that sorted it will be a matter of booking the flights and hotels.
You can always post on here or the community board for recomendations on hotels, things to do in each area - theres a thread on the community board already about NY

Your other option is to look into rail travel - there are some organised rail journeys across the states which I think look interesting as you will see a lot more than flying and you have the time to do it
 
i would love to do this for a couple of months - its one of our dreams!! We are doing it on a much smaller scale next year - 16 days travelling around California, but given the chance I would do what you have the chance to do!

I have got loads of guide books and am making lists of everything I want to do in each city next year, and working out from that how long to spend in each area, which helps with booking rooms (I'm not one for turning up in a city and praying that there is a room free somewhere!). Also most of the bigger cities have their own tourist info websites which have been really helpful. The Dis has its own west coast forums as well, people there have been really helpful to me.
 
Just a quickie.

But an interesting opportunity has arisen due to a combination of factors, that means I could fly out in mid September instead,

Lottery?

while a car is not required for new york, it most definitely is in la, and most other places out of the huge cities its a necessity, plus half the fun is the driving! I drove from Memphis to Chattanooga and through to Gatlinburg in Tennessee a few years ago using the old highways for the entire 400 miles (bar a 60 miles.) It really was something else, driving deserted roads and coming across amazing small towns. Listening to crazy right wingers on the am radio rant about how obama was causing the country to fail (6 months before the elections)

The way i planned was i looked at things i wanted to do in an area, then used travel guides, trip advisor and roadsideamerica.com to look at other items in the local vicinity. eg travelling to Chattanooga i wanted to see Rock City, (if you're near here go!) via the internet i then found out about the Tennessee Aquarium, The Choo-choo and Ruby Falls. 2 incredible attractions i never would of seen otherwise, but would return to at the drop of a hat.

book wise the dorean kinsley eyewitness travel guides are fantastic, and normally bang up to date.
 











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