More Difficult Choices

Last week’s post on aircraft provoked more comments from Readers than just about any other piece at this blog.

So this week I’m going to do something quite different.

The scenario:  you are going to do a road trip in Italy which will more or less follow the old Mille Miglia race course.  It will not be a race — in fact, you will end up driving quite slowly, stopping to enjoy all the wonderful views and other attractions along the way.  The only stipulations are a.) that you are in your early thirties, and b.) that whatever car you choose for the trip will be mechanically sound (i.e. no breakdowns).

To make it even more interesting, whichever car you choose will involve a mandatory traveling companion of similar vintage, and your choice therefore requires you to pick not only the car, but the companion as well.  You may not choose or substitute any outside the pairings as listed.

Choice #1:   1958 Lancia Aurelia B24 and 1958 Sophia Loren

Choice #2:  1968 Morgan 8 and 1968 Grace Kelly  

Choice #3:  1967 Austin-Healey MkIII and 1967 Gina Lollobrigida


Choice #4:   1965 Ferrari 330 GTS Spider and 1965 Suzanne Pleshette   

Choice #5:  1959 Corvette and 1962 Ann-Margret 

Choice #6:  1958 Mercedes 300 Roadster and 1958 Elizabeth Taylor

One choice, and one choice only.  Enjoy the trip.

Update:   I fixed the date of the Corvette, and of Ann-Margret just a little (she would have been 18 in 1959, shuddup you pervos).

Also: what part of “you’re not going to experience car trouble” was not clear?


  1. Easy. #5. Two reasons. First, 1963 Ann-Margret trumps all the other women. Second, only the Vette and the Mercedes meet any reasonable definition of “reliable.” And you do realize that the pictured Vette is not a 1963, but a 1958/9, right? 1963 was the first year of the Stingray.

  2. I ‘ll pick #5. My aunt had a 1959 Corvette. It was blue & fun to ride in. By the way, she was also blond & blue eyed.

    Here’s one to add to the list. About 15 years ago I went to a classic car show in Ohio. There was a beautiful lime green 1957 Ford Thunderbird convertible on display. You should add the car & its former owner to the list above. The reason? It once belonged to actress Kim Novak.

  3. I really like the looks of the Morgan, but I’ve never been a gearhead, so what I know about cars could fit in a thimble, twice. So I’ll go with Suzanne Pleshette & the Ferrari. I’ve always been a sucker for looks like hers, and as dakota says “that husky voice”! Also, she was the least famous of all the picks, so she probably had the smallest baggage train (real & imagined) that would follow our tour.

  4. Drive through Italy, and we’re going to stop, a lot.

    With a woman who speaks the native, her, language and mine and probably has a wealth of insight into the country and culture. Who’s going to carry her looks and poise into her old age but the thirty something version.

    A little drinking, a little dancing, a little extra time to get the car fixed if something tragic should happen and it breaks down and I’m stuck with Sophia Loren for just hours and hours, overnight, a lot, even.

    #1 please.

    out of curiosity, you ARE going to let us in on your choice, yes?

  5. I’m going with number #2. I’ve always had an affinity for Morgans and, well, Grace.

    Along with the Corvette there’s another mis/incomplete identification. In #6 the car in question is a 1957 not a 1958. This particular example is the one originally owned by Natalie Wood custom ordered by her at age sixteen or seventeen in pink IIRC. Paring it with Elizabeth Taylor is a sacrilege who in addition was a very high maintenance woman.

  6. “A strange game. The only winning move is not to play.”
    It’s indeed a strange collection when Sophia Loren is probably the most normal woman in it. Plus, all these women are technically old enough to be my mother. (If I were going to my mother’s generation, I’d want Ava Gardner, but that’s just me.)
    For pleasant traveling and conversation … #1.
    For pure, stunning beauty and nymphomaniac delights … #2.
    For curiosity, she couldn’t be as stupid as the characters she played … #5
    For petulant difficulty, arguing all the way … #6.
    All beautiful and unreliable, disloyal and expensive. So are the cars.

    1. Mostly agree. None of the cars are unacceptable; most of the women would make good short-term companions for all practical purposes. But Sophia…

      Time to go watch “Houseboat” again.

  7. Number 3, the Healy and Gina, both would be a lot of fun, I done a lot of miles in that car and never any with an Italian beauty. Close runner up would be Number 2.

    As said about number 6, the pairing of a beautiful difficult woman with perhaps the finest production sports car in the world. Easy decision on that one, walk away, do not look back.

  8. Cool cars and hot women. All good choices, but there is one combo custom made for me.

    I watched Route 66 when it was new and Ann Margret was my poster girl (if I had had a poster on the wall).

    Scenic drive on curvy mountain roads, stopping at some little roadside café for lunch, one of those amazing multi-course meals at some little place in the mountains, followed by a night of passion, a leisurely breakfast in the morning, and another day of new sights and sounds. I may have once driven a little bit of the northern part of the route, although in an Opel sedan, with a one year old baby in the car with us. Where do I sign up?

  9. #1. The Lancia and Sophia. I’m willing to bet that one night with that woman in her prime would be enough to make you forget the English language.

  10. Number 4 —- because vintage Ferrari in Italy = instant respect anywhere you stop — but they will also expect you to spend $$$$ like a Ferrari owner so I’m assuming that’s part of the deal.

    Arrive in combo # 5 or 6 and they will expect the same level of spending but you will not get any respect.

  11. The Corvette and Ann-Margaret please. The Corvette pictured is a 1958, but a Stingray convertible would be fine.

  12. I’d start with #3, assuming the car has been gone over by an expert mechanic before the journey. I had a teenage crush on Gina, so that and her language fits the trip.
    I’d have to come back the next four years and go right through the list, a different pairing each year.
    BTW, I’ve been on the roads of the Mille Miglia, and I honestly don’t know how those race drivers managed that twisty, narrow, bumpy road in one continuous run. Some of the sections I drove in the mountains were not much more than cart paths.
    Given the company and the road, I might have to make the trip in about a month, not in less than a day like the racers.

  13. 1963 Corvette and 1963 Ann-Margret.

    I like red things. And the car isn’t bad either.

    I love the fact that every one of us, to a man, also reads into the assumption that because we’re in our early-thirties, that also means there will be a near 100% chance of sexy time with our female companion. The pragmatist in me would choose the woman with a map and the ability to read it, a cheery disposition, and loose enough morals to make the unspoken assumption most likely.

    1. There was a car? I just saw Sophia Loren needing someone to bring her a cool drink and shade.

  14. You did say no breakdowns? Something of a miracle with a Morgan +8. I had one in the 70’s and it was trouble from new, (ignoring the enormous amount of pleasure it gave me otherwise). no luggage space at all! Not suitable for a lazy tour through Italy. The same also goes for the Healey, (though some luggage space – not much). Also not suitable for a lazy tour through Italy. (I had one of them too). Since the parameters were for a suitable for a lazy tour through Italy, I would be tempted by the Lancia Aurelia or, better still, an Alvis TC21 Drophead. I found the ladies chosen to not really suit me as a boon companion, kin I have Kate Bush please?

  15. I’ve long been a fan of Sophia Loren. In fact, it is one of my earliest lustful memories that I recall watching a movie on TV in which Loren wore a white peasant blouse, with glimpses of mammaries offered in tantalizing vagueness. I don’t remember much more about the movie except that a major plot point seemed to be that the characters had to move this REALLY BIG cannon from somewhere to somewhere else. So distracted was I by Loren’s pulchritude.

    But I also really think that Ann Margaret looks like she’d be more fun. And I’ve also always liked that vintage of Corvette.

    1. That was The Pride and the Passion with Frank Sinatra and Cary Grant. And a very large cannon needing to be hauled halfway across Spain.
      And I’d go with Loren but scrap the Lancia and go with a ’67 Alpha 1750 Guliette Sprint Special aluminum-bodied fastback. Only because I had one and let it get away…

  16. Unfortunately I am at a severe disadvantage here, as I’m young enough to not know anything about the personalities or disposition of any of these traveling companions, which of course is probably the most important part of this selection, as the right (or wrong) woman can make your life a joy or living hell even more so than the vehicle. I would have to do some research before properly answering.

  17. Driving through Italy with anything or anyone not Italian, no way! So absolutely #1. Actually, I have always thought that Sophia was and is one of the most beautiful women in the world. I was in the Rome airport in 1971, traveling to Brindisi to go to San Vito dei Normanni AS where I was stationed. Sophia came walking through the airport, surrounded by carabinieri, an absolute vision of beauty and grace. Still have a huge crush on her. Ann Margaret is a close second, partly because of her support of our troops doing USO shows with Bob Hope. Beautiful woman and a class act.

  18. Choice #4: 1965 Ferrari 330 GTS Spider and 1965 Suzanne Pleshette
    Simply because she has always struck me as a good conversation companion, need someone intelligent to speak with on long drives.

  19. #2. You said no breakdowns. And who wouldn’t want to tour with a gorgeous woman who positively exudes elegance. Tough choices, mate. As much as I love both Ann Margret and iconic Vettes, they both just seem to be too Yank for an Italian gambol. If it were a Rt A-1-A or Pacific Coast Highway run, they’d be my go to, but it’s Italy, man! If ya don’t care where ya are, ya ain’t lost!

  20. As someone who owned – and drove – a 67 330GTC for 40 years, # 4 would be my choice: Suzanne is a bonus.
    The 330GTS was not put into production until late ’66 at the earliest – Ferrari was enjoying a pretty nice run with the 275GTS in ’65 & ’66.

  21. I’ve sat in the modern version of the Morgan and it was love at first sit. And then there’s Grace Kelly. Unfortunately you specified 1968 when she was Princess of Monaco. So that choice is out.

    I’ve seen a Healey and I can’t fit behind the steering wheel – not unless I do a Hightower and rip out the front seat.

    Liz Taylor is out too.

    It’s Italy so it’s got to be a Ferrari. #4 it is.

  22. you had me at Ann Margret regardless of car and although the car is mechanically sound, there’s still running out of gas.


  23. 1959 Corvette and 1962 Ann-Margret with me when I was 26 years old. The Corvette is a plus as a Chevy Nomad with blacked out tinted windows and mattress in the back would be better.

  24. I once had the clutch cable break on my VW Square Back pulling out of Florence heading towards Nuremberg in 1968. I made it back all the way knowing how to get gasoline and then head out in second gear bouncing a bit then raving up and then changing up gears. I did the whole trip in one long very strange day and later after i got back found out there was a cable that had failed that connected to the clutch, not an expensive fix but glad I made it back after stopping and starting a few times on the Autobahns in Italy, Austria and Germany. Bringing that broken bird back home

  25. I was thinking that Suzanne Pleshette with the Ferrari, but DamnYankee makes a good argument for a native speaker, so, I choose La Lollo with the Ferrari, but if you insist, the Austin Healey will do, too.

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