Many moons back, I set up a scenario wherein you were going to drive around Italy with a beautiful woman, in a beautiful car. (For those of shorter memory, or who missed it, here’s the premise.)
So here’s another one, closer to home. The route I’ve chosen looks like this: east-west along U.S. Highway 50, then a cut south before Cinci and Lexington (because ugh), then westward eastward along U.S. Route 70 to the Atlantic. Starting point is Winchester VA (red dot #1) and the finishing point is wherever Dot #2 is, on the coast.
I’ve done the U.S. 50 bit myself before, and it’s beautiful. I’ve done a little bit of U.S. 70 (from Nashville to Charlotte), and it’s also lovely. The road is twisty, the atmosphere romantic, and the scenery beautiful — from open fields to forested mountain passes.
The whole trip should take about 5-6 days, about 7 nights — because this isn’t a race.
So here are the choices (and remember, no switching around; the choices are as set down), and the women are as pictured, not how they would look today. And yes, assume a little romance along the way.
Choice #1: 1965 AC Cobra and Dita Von Teese
Choice #2: 1965 Shelby Mustang and Kelly Brook
Choice #3: 1956 T-bird and Lynda Carter 
Choice #4: 1961 E-type and Liz Hurley:
Choice #5: 1959 Mercedes 190 SL and Laura Linney 
Choice #6: 1965 Ferrari 275 GTB-4 Spider and Amy Adams 
Your choice in Comments; I’ll tell you mine tomorrow.
#4, obviously.
Nice to have a roof overheard if it rains.
And that long hood lends plenty of room to stretch that Liz Hurley out properly for mounting in an obscure off road setting.
Some tough choices, my friend.
Not knowing any of the ladies except by reputation madam von Teese, I’ll go by the cars.
Depending on expected weather conditions either the Mustang (because of its hard top) or the Thunderbird would be the car for me.
All of the ladies are fine and would make a wonderful traveling companion for this old man. He might need help getting in and out of the cars and the services of a chiropractor when the trip was finished but that’s a small price to pay. I’ll base my choice on the car and I just have to go with the #1 Cobra. Its noisy, leaky, primitive, and there are plenty of modern cars that go faster and handle better. Even so I’ll go for voluptuous curves and total impracticality. Kind of like your choices in women.
Since we’re not allowed to mix and match, my choice would be Lynda Carter and just about any old car.
And dude, choices 4 5 and 6? Get that damn Euro-trash off our American highways!!
Give us a mid-80’s Monte Carlo SS, a early 90’s Camaro with mis-matched tires and bubbly paint on the hood, and a late 70’s Trans-Am with one missing T-top. Now you’re talking!
No Option #7 Liz Cheney in a Yugo?
No pictures because, well, I don’t want to ruin that many monitors and keyboards.
JQ
Sir, I’m triggered by the mere thought.
Brain bleach mechanisms engaged.
Has anyone noticed that looks wise Liz is Hillary in training or is that just me.
Damn you for including Linda Carter and the T-Bird!
I thought I’d go with #1 right from the get-go because I’ve always been curious about Dita von Teese, I mean, the name says it all. Except I really doubt the tease part.
But Linda Carter, and a T-Bird?
Survey says; Choice #3.
Dita will just have to wait till next time.
Ok — First the Cobra and the GT 350 are out because as you say, this is not a race and those are thinly vailed race cars – hot and loud and not suitable for the task. But they would be the choice in my 20’s.
The T-bird and the 190 are also out because no power. Even though the route is not interstates, I’m not interested in being at the front of a long line of f-150’s and SUV’s crowding the bumper.
That leaves the Jag and the GTB. Both of which, will probably result in an extended, unplanned Hotel stay in some small town in the middle of nowhere. So the real choice is Liz or Amy for that extended Hotel stay.
The Jag it is then.
Sorry, this will take a bit longer than 5 or 6 days, we need pit stops longer than an EV needs to do justice to this trip:
https://kybourbontrail.com
Any of the cars are fine, but the babe has to be Linda Carter.
#4, e-type and Liz Hurley.
Number 1, thank you kindly, good sir.
I would die a happy man.
There are really only 4 choices. Laura Linney and Dita Von Teese are out; the former because she’s an insufferable lefty bitch with whom I wouldn’t care to spend five nanoseconds in a car, let alone five days, and the latter because despite her old-school retro appeal, I can’t trust anyone who would marry Marilyn Manson. I like my kidneys (and genitals) intact and where they are, thank you very much.
So, the list:
#4 Elizabeth and the Jag, because despite their beauty, they both strike me as being impossibly high maintenance.
#3 Lynda and the T-Bird. No complaints here, it’s just where they ended up.
#2 Kelly and the Mustang. I know very little about her but I’d love to get to know her better, and the Shelby would be the easiest to work on for the inevitable mechanical issues.
#1 Amy and the Ferrari. The all-American girl (who by all accounts is a very nice person) and the all-Italian roadster. Give me a Rand-McNally atlas, a cooler full of snacks, and I’d love to get lost with her.
Screw going to the coast. I’d START in Cincinnati (’cause I’m already here) and take 50 through Ohio to where it crosses the river into West Virginia, enjoy the very pleasant ride on 50 through the coal mountains to southern WVa and stop in Randolph county. Spend the rest of the days and nights in a hotel in Elkins (or maybe the Greenbrier, which is just up the way) with .. Kelly Brook (love the high beams, Kell) if I GOTTA drive the Mustang.
#4: Lynda and the T-Bird, because trunk space for all the stuff she’d bring along. AND she’s the only one I could put up with for 5-6 days for all the reasons cited about the other women above.
Yeah, I’m just a hopeless romantic, aren’t I?
“… not how they would look today” is the key, of course, for the women and the cars and … me.
All those cars and all those women would break your heart. Most of the women would also break your head, as already noted by others.
Now excuse me, I have a time machine I have been working on.
NOTA
I’ll take a ’74 VW Bus and Gloria Talbott.
Alas, Ms Carter while still quite handsome, is 71 years of age…. Now, if we could somehow travel back in time…..but no. I obey the laws of physics.
So Ms. Von Teese for the win.
Liz and the Jag, by a nose over Wonder Woman and the T-bird.
You know you are getting old when the car is more important than the lady.
Tie for first. Amy with the Ferrari or Lynda in the Tbird. I’d need 2 trips to determine the winner.
Kelly and Liz would be nice concession prizes:
Linney and Dita, hard pass.
Oh, and for those concerned about lack of roofs?
I think that I’d just find a convenient hotel to wait the rain out in…
FWIW, and at the risk of Ford Apostacy: Having owned both a ’68 and ’96 mustang, I have direct knowledge of how not good at actually being a car the early mustangs were. The later mustangs were infinitely better at being a car, and even then, they left a lot to be desired. I’ve never driven a Shelby, but I can’t imagine even a master could have done much with the platform he had to work with.
So, I’ll have to go with #6. Ms. Adam’s reputation for being a nice person and my long standing, well documented thing for redheaded women pretty much over rides automotive considerations, but I figure I can’t go too far wrong with a mid 60’s Ferrari.
My choice would be #4 and Ms. Hurley.
But, Kim, I’ve got to pick a few nits:
1) The route on “70” is EASTWARD (did you get lost a lot whilst in the army for your failure to note the cardinal points on the compass?);
2) The 4-cam 275 engine was never available in the 275GTS, but if you could come up with a 275GTB/4 NART Spyder (see “That Red Thing” in the original “The Thomas Crown Affair”). Having been a long-term owner of a 330GTC, the GTS version of that car would be my choice as it is a much more pleasant car to drive than the 275, having more usable torque.
I actually had an E Type (1962 admittedly) they were utter pigs to get in and out of. Therefore it had to be the Mustang (Hardtop for inevitable rain) and Kelly Brook who seems like someone I could happily talk to.
All those open-top cars are out: I’m 6’4″ so I want something between my head and the ground if the car ends up upside down. Fortunately Ms Brock seems a cromulent companion.
I too am of average height (6’3 1/2) so headroom is a concern in most sports appliances…
The three of us see eye-to-eye.
.
Amy Adams because LDS… her hobby is cooking and family.
Conveyance is irrelevant.
The Ferrari for me…Amy seems the mostly likely to not be a loon and beauty only gets you so far when confined in a small space together for a week. I would also time the trip for late September through mid-October; I live down there by Dot#2 and the North Carolina coastal plain is not the place to be driving an open top car in July or August.
The redhead and whichever car comes with. I’d probably go with the southern route (unless its midsummer hot and nasty) since I live just off 50 in WV and get to experience it all the time.
You had me at the ’56 T-Bird and Lynda Carter.
Two thumbs up.
You probably don’t want to drive westward to get to the Atlantic Ocean.
I think I must be getting old and crotchety. If I could have that Cobra for the week, I think I’d rather leave the companionship behind and just concentrate solely on the pleasure of that automobile.
Plenty of time later to find and enjoy some lady.
Wonder Woman and the t bird would do nicely.
Liz hurley. Any car will do.
But she is probably the sexiest woman who ever lived.
#4. Mostly for the E-Jag.
The E-Type. The Stang is only for those with a heavy-duty licence.
Being the lecherous old fart that I am No1. My epitaph sould be ” He died happy “