A Jeepster is fairly reasonable. Not hard to find a v6 or v8 one. The convt top fits pretty well so it’s ok in the rain. Look around.
Try to find an owners club for these, get an idea of what it takes to own one. I keep admiring the early Land Rover’s running around town but we have a restoration shop that knows them inside and out just up the road.
I can’t imagine taking a WW II Jeep on a road trip. Ten miles was about my limit.
As a senior in high school my best friend had an old Willys wagon; 49-51 I think it was. We made a 100 mile round trip to the lake one weekend and it was torture.
The axle ratio was something like 5:30 or 5:40 and that engine was screaming at 50 MPH. Deaf when we got there… 
I can’t imagine someone taking a road trip of any length in one of those unless the gear ratio was altered.
Unfortunately Jeepsters were usually 2WD.
@JollyRoger:
You’ve gotten great input from the previous replies. It would help if we had a little more understanding on your expectations.
If money isn’t your concern, and you understand it won’t be a dependable vehicle but could be suited for fun driving around town, then yes, by all means, go for it.
As I remember, the Willys station wagons back then with the 4 cylinder engines came with the Borg Warner overdrive as standard equipment to keep the engine revs down at highway speed.
We had a pickup too for awhile. All stock. Yep, it was a tank. We put in a power r&p this past summer. Looking for new wheels/tires but am debating old/new styling. Steelie or alloy?. It’s hard choice on a 48.
I experimented with the tires that came on the junk Jeeps I bought. 2 were oversized and worsened the braking and handling. A set of OE style tires gave the best performance.
I once pushed the speed up to ~55 mph on the OE tires and when I got it back under control I was never stupid enough to try it again.
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To all who have responded: Thank you! I am humbled by so many responses, so quickly.
I will try to address the general themes of your answers. To reiterate, I am looking for something only to tool around, short distance, good weather, just for fun. My dad was in the Army, WWII. I’ve read stuff he wrote at the time speaking of hopping in a Jeep from the motor pool to go from here to there.
I have no plans of taking this on a summer vacation. That’s not what they were designed for.
I have searched for a local Willys club, with no success so far. But in this year’s Memorial Day parade for the first time, and we’ve been to the last 41 or so, there were about 7 or 8 Jeeps or Willys. I’m going to ask the mayor how they found these guys.
I know its going to cost some money, what doesn’t?
I recently found out a friend is restoring a Willys he recently acquired that had been sitting in the woods where he grew up and played war around when he was a kid. He is doing so at a glacial pace. He will be a good source of info. That is if he doesn’t kick me out for driving up with one ready out of the box.
Lastly, I hope it doesn’t take too long to learn how to double clutch.
Again, thanks to all. Does it always happen this way on Car Talk?
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Thanks for the informative reply. With your interests, it sounds like a great idea to get a good, running Willys. You’ll have to look far and wide maybe check out Ebay Motors, etc. You’ll want to find a shop in your area that works on older (pre 1970) cars, they’ll be able to help with the carb and ignition system.
Fun fact, I’ve heard it’s pronounced ‘Williss’, not like ‘Willy’s’. I don’t know if that’s true…
I can remember some tv ads from when Kaiser owned Willys, and it was pronounced Willies back then.
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It can be subjective, as far as pronunciation goes
Around here, there was a local politician who pronounced his last name a certain way
His dad, with the same last name, said his son was wrong about the pronunciation . . . !
You can start by just doing a google for WW II Jeep. Ton of info out there. Looks like in the $20,000 range for complete.
There’s your club! Now search for more members.
Have I created a monster here, or is this par for the Car Talk course?
Yep. 
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You asked about an old vehicle, something many of us relate to…
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