You should know the drill by now in these Tuscan-hillside towns? Persevere with trying to park at the bottom then lug it up, on foot, straight to the top.
That way, the inevitable church or cattedrale up there provides a calming sanctuary and after 20 minutes you'll have steamed right off, all ready for a fair-minded mooch on the way back down.
Except, the routine has only gone and been disrupted today. There's plenty of parking at the bottom and they've even laid on an escalator for the first leg of your lug.
That brings you up to Via Nazionale, which leads to the Piazza della Repubblica, which both deliver on the fairly familiar, Euro-feel front. You could spend all afternoon in and around here, it really is rather relaxing, but today it will have to wait for there's still some elevation to be gained.
 Already more than halfway up the 2,000 foot to the top.
On your way back down from the summit, in and around the Piazza della Repubblica, Sly declared this the 'best bruschetta ever!' and she should know, she's had a few.
It's a heck of a hike, less strenuous days have been had in the Lake District, and each and every turn reveals yet another uphill alley to a blind summit.
You will, eventually, reach the inevitable church that is the Basilica di Santa Margherita and just when you think you can't go any further, go a little bit further. That way, you'll finally arrive at the Fortezza del Girifalco.
Cortona is well known as any artsy destination, apparently, and the old fortress, inexplicably not shown, has three, or was it four?, floors of displays for only €5.00s. There's still some work required in Bob's jelly legs, however, because that lift is very much, just like them, FUORI USO.
Upstairs today, away from the windows and the requisite Renaissance, there's something more recent and a fantastic exhibition of abandoned theme park photographs.
Highlights include the, erm, Neverland Ranch and others elsewhere in the world. Jamaica? No, but there was one in Tanzania that has since reopened, they say.
It's not all about old log flumes, there are, not unexpectedly, fantastic views from up here as long as no cold fog looms. That includes the aforementioned church and the bastions of the Fortezza, which might be 16th century, they say.
Down in the surrounding countryside, forget about those rusty merry-go-rounds, you might see some musty berries-going-round. They're being delivered to the many wineries for which Tuscany is world-famous, of course.
Meanwhile, back down on Via Nazionale, an English-speaking travel company who might be able to help since SlyBob's level of Italian is, quite frankly, 'phrasebook'.
Now, here is hardly the heart of Chiantishire but there is still a certain 'type' of English visitor including those that live locally for half the year. Not wishing to stereotype, but go on then, that includes 'Pippa', probably, who is up some narrow stairs to a small office with an ineffective table fan.
You might want to pull up a chair...
It says here you organise wine tastings in the local vineyards?
Erm, yah, sort of, we just arrange the transport so you don't have to worry about being over the limit, yah.
Sounds good, do you cover
Umbria? It's only about 15 miles away, would that be OK?
Erm, sorry, yah, no, you still have to come to Cortona, yah.
So, we still have to come to Cortona?
Do you have any information on the local buses?
Erm, yah, no, if you're not staying here, most people come by car, yah.
Since SlyBob's not staying in Cortona, there's a potential negotiation in having them pick up, it's only 15 miles away remember...
You have a minibus?
Erm, yah, no, we use local taxis, yah.
Thinking ahead... And you've negotiated some kind of discount?
Erm, yah, no, you pay us per person to arrange the taxi for you, yah. We take you in groups if there are enough people, yah.
Same price for sharing?
Erm, yah, per person, yah.
But you don't arrange transport outside of Cortona?
Erm, yah, no, sorry, yah.
Well, thanks anyway, and it should have been left at that but Bob couldn't let this go...
So we drive here, take a taxi, the comfort of which depends on the turnout,
only to have to spit out the Sangiovese defeating the whole point of the afternoon?
Or, we could just try and make our own way there?
Get much business do you?
Starting to pity young 'Pippa', a bit, she was only here for the summer and this was her family's 'business'. By 'business' it's meant calling Chianti-Cabs on your behalf and charging you thrice the price to share with some strangers.
Not wishing to stereotype, but go on then, perhaps 'Pippa' is really 'Paola' and the mafia princess just picked up the accent at finishing school. This is just a front for the real 'business' and €40 each, to share a taxi, isn't the only racket they're running?
L'esprit de l'escalier,
literally, on the way out down the narrow stairs.
 Perhaps they do? Perhaps there are that many posh mugs, sorry, punters here.
Never did make it since them local buses turned out to be rubbish but advising trippers speak highly. It's only 10 minutes from Cortona in a taxi and if you're in the area, give SlyBob a ring and we'll arrange one for you. €35? Each.