Is Milano just an airport entry, or do you plan some time in the city? If the former, I’d lean towards reversing the trip, so that you start without the car in Florence, allowing you to walk around and get over jet lag before driving. Then either hire a car from a location you’re comfortable in Florence, or take train or coach to closer to your Tuscan countryside base & hire the car from there. From then on, you have the car the whole way, so you’re not having to carry heavy luggage (full of wine I’m sure ) on public transport.
However Ramon makes a good point about Lake Como, and the decision may well come down to what you want from Lake Como. If it’s a chilled drive along mostly deserted scenic roads then you might be a few decades late . For me it’s about whether you desire to venture out and about - to villages away from the lake and the normal tourist trail. Having a car for ~ 3 weeks does give you a little flexibility though, such that if you only used it for ~ 2 days out of 6, then there’s still value in keeping hold of it.
However to contradict myself, there is merit in Lake Como being the first destination (and IMO try to get there first, and then from there to Milano if staying there as well, not the reverse order that sounds more logical) if you choose to forego the car there, as walking in a somewhat more rural setting is a wonderful way to get over jetlag and to help you relax more quickly. If that appeals, it might be worth looking at a single base in Tuscany, not in Florence but near to it (let’s say a 10-30 minute bus ride). This allows you to keep the car, but leave it parked up when heading into Florence for the day / evening. It also means you’re still pretty well-placed to explore Tuscany without having to fear the central ZTL / one-way systems. Again the focus of this plan is to ensure you can drop the car at the airport and lift those heavy bags only as far as the waiting trolley. You’re also very much in control of timing your journey to arrive at the airport on time.
Where to start the hire from may require some thought.
- If you stick with your schedule of Milano then Como, I’d be tempted to hire on leaving Como (or perhaps after a couple of days there).
- If you reverse Milano and Como, then hiring from Milano is a possibility, but put you in a big & busy city to start (ugh!), but get a clear route out and you’ll be fine. You could take a train, but although Milano-Torino is ultra fast, Torino is just as horrific for driving in. Looking at Trenitalia.com, it seems Alessandria might be a decent option e.g. Partenza 11:25 Milano Centrale Arrivo 12:49 Alessandria (direct) on a cheap regional train. From there it’s maybe a 50-70km drive on pretty decent (unstressful) roads to get to Barbaresco / Barolo villages.
- Taking train to Torino allows you to change for the new SFM route direct to Alba (it used be more awkward). Hiring a car in Alba might be appealing, as you’ve then got a very short drive.
You’re right to avoid driving in the cities. It’s doable, but Italian driving is too fast and skillful, that visitors often end up causing problems because we’re not. If you ever do need to drive into a city, I’d recommend planning the route out in advance, targeting a car park a moderate walk (say 5-15 minutes) from the ZTL zone which typically marks the centre of the city and which entry into by accident will cost you a hefty fine. This goes for even moderate sized cities, but for somewhere like Alba, Acqui Terme etc. you can get closer.
Outside of the cities, driving is pretty good, though there are masses of signs on Italian roads, with signs for businesses mixed in with those to nearby towns / villages and touristic destinations. The Autostrade are of variable quality, but at least pretty consistent layout. You may hit the odd toll section, but it’s generally small change. One bit that can catch you out, is that when turning off, it usually sends you in a sharp loop to your left (after bearing off to the right), so do obey the speed limit shown as it’s a very sensible speed. Petrol(Gas) stations are all over but many have now moved to unmanned, with a variety of systems. Common is one central machine where you select which pump you want want and how much of what type of fuel, then you head to that pump and fill up, with it stopping once you hit your €20 or whatever. The large autostrada service stations are usually fill it up and pay inside, whilst we do rather like the old-school manned places where they fill it up for you, for as much as you want. They aren’t overly expensive considering, but are a dying breed.
If you aren’t a fast driver, or get rattled by people driving 2 feet from the back of your car (I told you they were fast and skillful), then one trick we use is if we see someone doing this behind, we’ll pull into a petrol station but just drive through, allowing the usually impatient Italian driver to be on their way. More normal, and scary the first time you see it, is on a normal road, one lane in either direction, they use an imaginary middle lane to overtake, relying on drivers in both directions to pull over a little to allow this. They’re skillful and it works, but puts the fear of god into many visitors envisaging a head-on crash, but there are always inches to spare so trust them.
Lots of rambling from me, I hope it’s helpful, but do fire back questions if anything needs clarification, or to bounce ideas. I can help better with Piemonte than Toscana accomodations / places to stay.
regards
Ian