A 9-day itinerary in Tuscany, by Doron Maoz. We’re a couple in our late fifties who have lived in Europe for many years, get around by car and are very experienced travelers. We’ve just come back from a week and a half in Tuscany. I’ll try to share a few insights and some recommendations here that I think can help people plan their time in the region.
I hope it’s useful to someone.
What's in this article:
Introduction and Practicalities
For planning, we put all the points of interest we wanted to see on a Google map, and I expanded each point with the sub-points we intended to visit (for example Cinque Terre, recommended restaurants, special viewpoints and so on. Florence: points of interest, favorite routes, parking lots, recommended restaurants and so on). Then I connect a route between the points in the way that seems most logical to me (in terms of driving, points of interest along the way, the sites themselves, the time worth spending at each place and so on), and then we move along the route, always booking accommodation for the next day or two according to our planned progress (we almost never stay more than one night in the same place). Of course that’s less possible in July and August, when everything is packed, or with a family with kids or several families together…
Hotels: for us, the hotel is meant for sleeping at the end of the day; it should be clean and have free parking (we arrive at night and leave in the morning). We changed hotels almost every day. Two were truly exceptional in quality. The rest were great overall. There’s no point naming places, because there are endless options and in the end everyone books through Booking.com.
I haven’t listed every place we visited, only those worth a special mention (more or less positive).
Tips and Insights
Car and parking
I don’t think it’s right to travel in Tuscany without a car (I’m not talking about the big cities, but in general). There’s no problem traveling with a big car. In any case you don’t drive into the towns or city centers (it’s simply not allowed). There are very fairly priced paid parking lots (usually with parking meters) everywhere you need them. All the free parking lots I mention were valid at the time of our visit. I assume that doesn’t change often, but everyone should check whether it’s still the case. One more word about parking meters: no two are alike.
In one you have to type the full car number, in another the parking space number on the ground, in a third only three digits of the car number (because there are letters too and sometimes more than three digits), the fourth doesn’t take credit cards, and the fifth… you get the idea. The solution: ask a local for help (who will usually also be surprised by how clunky it is).
A tip from the Check In Out team: Booking a rental car in advance is recommended and will save you the hassle of comparing prices and finding a reliable rental agency during your trip.
We’ve written a whole article with tips on renting a car abroad.
Weather for a trip to Tuscany
I wouldn’t recommend traveling in July and August. The heat is very heavy, and being outside is hard and draining. We had around 26 to 30 degrees Celsius, and it was pretty tough to be outside all day every time. The weather can be changeable: not every rain forecast comes true, and vice versa. I recommend not changing your route in advance based on weather forecasts, but simply changing plans ad hoc if needed (swapping days, moving routes earlier or later and so on).
Toll roads
The toll roads inItaly are the best of the best, but they’re not cheap. The motorway from the border with Austria (via Innsbruck) to La Spezia cost 51 euros in total one way (in two separate sections). Choosing ordinary roads would have added about five hours to the journey… On the way back from Florence the cost was about 41 euros.
Navigation
Both Waze and Google Maps work brilliantly. During the trip itself we turned off the option to drive on toll roads, and enjoyed local roads and beautiful routes.
Our Tuscany Itinerary
Cinque Terre
A must! You can do it in one day from morning to evening, using the train (which leaves from La Spezia) to move between the three northern villages, and between the first two I’d recommend walking. Bear in mind that at the time of our trip the path between Riomaggiore and Manarola was closed for renovation (it reopened in 2024).
For parking, you can park in free parking along a stretch of about three hundred meters not far from the train station (a few minutes’ walk). If you arrive by 9:30 in the morning, your chances of finding a space are pretty good. If you don’t find one, the other side of those 300 meters is paid parking (until eight in the evening, after which it’s free). It costs half a euro an hour, paid at a parking meter.
As for train tickets, on the one hand it’s well worth buying them online, because the lines at the station and at the station’s ticket machines can be unbearable (really!). On the other hand, on the day we arrived there was a train strike (an Italian strike, of course, where you can’t know whether there will be trains and when, until five in the evening…). Luckily we didn’t have tickets in advance (they’d have gone in the bin, since they can’t be changed), so we stood in line and bought them for the next day. When we came the next morning (a Saturday), we couldn’t believe our eyes.
Endless lines stretching about a hundred meters outside the station (including in front of the machines). The cost per adult, including the shuttle up to Corniglia and back, was about 18.5 euros. At the time, masks were required on the shuttle, though not on the train.
• Don’t skip the two towns of Porto Venere and Lerici, on the coast not far from La Spezia.
• In our opinion you can skip the town of Carrara (the one with the marble…).
Lucca
A really charming town. Besides a bike ride around the walls, it’s worth exploring the old town on foot, crisscrossing its streets. A nice tip: about 20 km north of Lucca there’s a special ancient bridge called Ponte del Diavolo, the “Devil’s Bridge”. It’s worth a quick visit; a lovely place. In Lucca you can park for free in the parking lot opposite the amusement park, a five-minute walk from the old town.
Pisa
There’s a big free parking lot, Parcheggio Park Brennero. Note that half of the lot is paid (marked with blue lines) and half is free (marked with white lines).
The parking lot is huge. The walk to the tower takes about a quarter of an hour (when we arrived, a few days ago, they were filming a movie there and had closed off the whole area. We had to make a detour on foot of about 2 more kilometers until we could get close to the tower from the other side, and even then not very close).
Volterra
A charming village with a breathtaking view. Worth a visit and a wander through its alleys.
You’ll find lots of material about it online.
San Gimignano
No need to say more. A must.
SentierElsa: Ponte di San Marziale Entrance
Parco Fluviale Alta Val d’Elsa: a lovely stream with an easy, not particularly long walking path (you can walk there and back as far as you like) with lots of refreshing swimming spots for summer and hot days in general. Not far from the entrance (something like 200 to 300 meters) there are two free parking lots this is one, and this is the second. The entrance to the stream is right in town, so just ask locals where it is.
Siena
One of the highlights of a visit to Tuscany. An enchanted and enchanting medieval city. Despite the large number of tourists, the old town is a living city that simply goes about its life as an ordinary, lively, vibrant town. No need to say more. Don’t miss it. We devoted something like 8 hours to the city (plus dinner at a great restaurant) .
Montalcino
A very pleasant town. The supposedly beautiful viewpoint is from the top of the fortress at the entrance to the town (through a restaurant, for 4 euros per person), but… there’s a free viewpoint that’s just as good at this spot. You can also park the car briefly right there. Couples owe me 8 euros…
The Val d’Orcia: what more can be said about this place that hasn’t been said already? All the wineries, the cypress avenues, the green and golden hills… there are no words. I’ll try to give a few of our insights briefly:
San Filippo waterfalls (Bagni San Filippo)
Hot sulfur springs, gathered in a row of pools flowing out of a huge rock. Temperatures are around 38 to 40 degrees Celsius. In our eyes it’s a must. Our golden tip: go there an hour before dark and stay for about an hour and a half. Very worth it. There will be relatively few people, and the atmosphere is simply wonderful. There’s paid parking (meter) very close to the site, and also free parking a few hundred meters further on. The parking fee is negligible, and the paid parking (you only pay until 20:00) is in a spot that seems “more right”.
Rocca Aldobrandesca
A pleasant town with a lovely tower viewpoint. The road there (like everywhere in the valley) is beautiful. When we were there (a few days ago) the fortress was closed and we couldn’t go up.
Quercia delle Checche
A huge oak tree, hundreds of years old. In my eyes a must-stop. It’s right by the road and you can park for free next to it. Amazing.
Pienza
Take the SP18 road and climb up to Pienza. In our eyes one of the most beautiful gems of Tuscany: a small, enchanted town. Organized parking for a modest fee at the entrance. Get lost in the town (it’s tiny). You won’t forget your visit. One of the problems with Siena and Pienza is that they set standards that are very hard to compete with…
Montepulciano
A town that isn’t small (compared to the other towns), with beautiful views and steep ups and downs within the town itself. As usual, metered parking at several points (after Pienza it’s hard to get excited…).
Arezzo
For us, Arezzo was quite a disappointment. Not that it isn’t pretty, but it’s a relatively big city, and after Siena it doesn’t really have much to offer (unless you’re fans of specific art). A tour of an hour and a half was enough for us, plus a great restaurant that wasn’t expensive, which we found in one of the alleys.
The SP222 road
To do the SP222 road properly, we first drove to the town of Colombaio, and from there climbed up toward all the “usual suspects”: Radda in Chianti, Panzano, Greve in Chianti and the like (there are quite a few). In all the towns it’s worth stopping for a short wander. The real fun there is the drive between the towns and the views along the way. In the town of Panzano there’s a butcher and steakhouse that’s crazy and famous.
We didn’t book far enough in advance, so all we could do was drool and watch the diners. Meat lovers should book ahead.
Florence
No need to say more. A wonderful city. One day was enough for us to see
the highlights at a relaxed pace, including the Uffizi (we went to the Piazzale Michelangelo viewpoint
the evening before, but could easily have gone on the day itself). Our tips for the city (beyond all the usual things): go to Piazzale Michelangelo for the view over the city in the last two hours of daylight. Right next to the viewpoint there’s a large metered parking lot.
In general, in Florence you can park the car for free in this parking lot and take the tram from a hundred meters away, from Nenni-Torregalli stop to Valfonda (Santa Maria Novella station). It costs 1.5 euros per person each way, and you have peace of mind all day. You buy the ticket at a machine next to the stop in a quick, simple process. The lot is next to a huge shopping center with lots of cars. I recommend parking where I marked and not close to the mall itself, because this lot is open 24 hours (it has no gates), whereas the part next to the mall can sometimes close at 21:00.
There are three towns we didn’t have time for, and I think they’d have been worth it: Cortona, Vinci and Pistoia.
Enjoy your trip, everyone.
