Tuscany/Umbria/Puglia 16 nights May 2026, Itinerary and Transportation questions

I would rent a car in Siena to visit Montepulciano, Pienza, and also to drive to Orvieto. Going from Siena to Orvieto by train takes considerably longer.
From Orvieto you can consider visiting Civita di Bagnoregio. It's a quick day trip.

I would keep the car to drive to Puglia. I know it's not a short drive, but it's all freeway. I would even consider driving to Pescara then down the coast to Puglia. Only slightly longer but it's also all freeway, and the drive through the Abruzzo mountains is epic. If you take the interior way through Benevento, watch out for the speed traps on the State highway between Caianello on the A1 and the A16 freeway junction near Grottaminarda. The police along the way will love your money. Pay attention to Waze (or GoogleMaps) speed camera alerts. If you take the Abruzzo route through the Adriatic coast, the speed limit is higher (130 km/h=80 mph) so less chance of getting zapped.

Regarding minimizing hotel changes. You plan to stay in Locorotondo to see Alberobello, Cisternino (I might add also Ostuni) and also in Polignano. But if you want to minimize hotel changes why not visit Polignano and also Monopoli from Locorotondo? They are only 30 min drive drive apart. If you prefer to do the reverse, you can also stay on the coast (Polignano or Monopoli) and visit Alberobello and Locorotondo and Ostuni from the coast.

Also Matera is no more than 90 min away from Locorotondo (including the time to find parking and walk to the Sassi), if you don't care to stay in Matera overnight.

Thank you Roberto for the reply.

I can see the point of self driving to montepulciano and pienza- concerns for parking? Getting lost? If I take a day from Orvieto and stay 4 nights in Siena I could use the car for a day trip to San Gimingnano and/or Volterra.

Thank you so much for the suggestion to drive through the mountains and along the coastline, we are definitely interested in this route. Which exact road would be best to get to Pescara- the A24 or E80? Those are the two suggestions on Googlemaps.

I have thought about skipping staying in Polignano a Mare, I am just wondering about enjoying the evenings in the towns. I would like to enjoy dinners in the towns and then drive back to, probably Locorotondo. How is driving at night? Meaning in Oregon we call night driving hard when small/windy roads have no lights and no lines (or reflectors) in the center or edges of the road.

I do think we will stay two nights in Matera for sure to enjoy the evening and not worry about such a longer drive back.

Since it seems you will be doing a good bit of driving, you might like to know that ViaMichelin.com will plot driving routes for you. If you zoom way in on a route, the especially scenic roads will be outlined in green.

The route to Puglia through Abruzzo from Orvieto is:
Orvieto A1 entrance.
freeway A1 toward Roma then Napoli (Naples), make sure you follow directions to Naples at the fork before the Diramazione A1 leading to Roma Nord.
East of Rome take the A24 freeway to Pescara
In Abruzzo that freeway splits into two freeways:A24 proceeding to L’Aquila, and A25 to Pescara. Follow the latter..
Once in Pescara you will switch to the freeway A14 Adriatica, all the way to Puglia.
E80 is the European Union number designation of the same freeway. Nobody in Italy has ever learned that numeration system, although it is on the road signs.
Once in Puglia there is also the Gargano Peninsula you could consider (like Vieste). If you plan to spend 2 or 3 nights in Vieste, or Peschici.

Wherever you stay with a car, including Siena, it is a good idea to have accommodations with parking and outside the ZTL (every town in Italy has a ZTL). There is plenty of parking lots outside the ZTL of any towns. I saved most parking locations in my favorites on Google Maps. Always remember that blue stripes on the asphalt means “pay parking” (not handicapped like in the US). So locate a parking pay machine to buy the ticket to place on your dashboard). Yellow stripes means restricted parking (could be handicapped, police, special vehicles, etc.). Don’t park on yellow stripes stalls ( although my father, a cheapskate, always parked on stalls reserved to police vehicles because, he said, nobody would ticket or tow a car which could belong to a police officer, believe it or not, it always worked for him, blessed soul). Also don’t park in pink stalls. Those are fro pregnant women or parents of under 2 year olds.
For Siena:
https://maps.app.goo.gl/raSbxCovQ22Bxiye9?g_st=ic
For Montepulciano I have two favorites (the latter is free, the former I don’t remember)
https://maps.app.goo.gl/KBa1sRJn1DtkjaZ9A?g_st=ic
https://maps.app.goo.gl/ve359kJGYvZEyEg69?g_st=ic
For Pienza (The latter may be closed on farmers market days, I think Friday mornings)
https://maps.app.goo.gl/jaXnztAb5aVfxUvh6?g_st=ic
https://maps.app.goo.gl/FGb3YxqwqJj1r9rH7?g_st=ic
For Vieste:
https://maps.app.goo.gl/ZeTZZht3RmJx31A19?g_st=ic
For Peschici (free next to this coffee bar)
https://maps.app.goo.gl/gDFTANp7oi3ojcnW8?g_st=ic
For Locorotondo:
https://maps.app.goo.gl/TotAbatWiJrwLZA66?g_st=ic (free on white stripes)
https://maps.app.goo.gl/7FvMjeSD7fMz9nAt7?g_st=ic
For Alberobello:
https://maps.app.goo.gl/8goFAXE7Vpt98Z1w6?g_st=ic
https://maps.app.goo.gl/w4cA3vqozWqgrSzs7?g_st=ic (fills quickly)
For Polignano
https://maps.app.goo.gl/s48WSeiTxV4uv1nDA?g_st=ic
For Ostuni:
https://maps.app.goo.gl/Rwq2PjTAiHswvCHj6?g_st=ic
For Matera:
https://maps.app.goo.gl/mjMxV4dxgn8vssHK7?g_st=ic
https://maps.app.goo.gl/iVM5YExq2sn78roP6?g_st=ic

All of the above are outside the respective ZTL and will require a little bit of walk into the historical core (ZTL).

Driving at night is not bad. Italian roads don’t have reflectors on the median, (which is white, rather than yellow like in US). Reflectors are on the sides of the road (red on the right and white on the opposite direction). Road lanes are narrower than in the US, and there are no shoulders, so don’t get distracted as you will be dealing with narrower spaces on regular highways. Lots of curves on Italian roads for sure, especially in Tuscany. Freeways are like Interstates in the US (actually better). Very few curves on freeways but tons of very long freeway tunnels (I hope you are not claustrophobic, as you will driving underground for miles, especially between Rome and the Adriatic coast through the Apennines mountains. Italians love viaducts and tunnels, and if there are no mountains, the freeway constructors will find one so they can tunnel through it rather than curve around it. In their mind freeways must be as straight and as flat as possible, no matter the cost.
On the freeways, the left lane is passing lane only (no cruising on it). You can’t pass cars on the right side on the freeway (must use the left lane). So get out of the left lane promptly after passing a vehicle)
Learn road traffic signs.
https://en.wikipedia.org/wiki/Road_signs_in_Italy
GoogleMaps or Waze are your friend.

Your plan to visit Umbria is weak, only visiting Orvieto. Umbria is fantastic, visit Gubbio, Assisi, Perugia and Spoleto. You need at least 5 days to do that. consider doing just Tuscany and Umbria.

Thank you for all the information regarding driving, will use it all while planning the drives. I know people said driving in New Zealand is so hard, tiny windy roads, it was easy to us. Iceland, not an issue at all for driving, dolomites driving was fine with one exception -the auto shut off while stopped with a stick shift, on a hill, in construction- those behind us were honking madly when the light turned green and we could not move- until we found the off button - didn't know this existed as we don't have vehicles that the engine shuts off while stopped.

Still working on itinerary that works for us.

I wrote a long contemporary trip report on my road trip through Umbria and Toscana. It includes a lot of my difficulties and frustrations with driving, as well as responses from other forum member sharing their experiences. It starts with my arrival in Florence. I'd been to Assisi for a couple nights several years before and wanted to go back for another look at the frescos. Assisi is well worth an overnight. I used the RS Italy guide book and Lonely Planet online.

I spent 3 nights in Orvieto on a previous trip.
Puglia is still on my list.

Chani, that was an enjoyable trip report. We are definitely trying to decide what transportation combination will work best for us.