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

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Planning our 4th trip to Italy and could use some input on possible changes to my plan---

2 nights Florence ( not into art, so figured this would be enough for us- train to next stop-yes I know bus is faster)

3 nights Siena ( one day city and one day tour to Montepulciano and Pienza (not into wine here for the scenery)- train to next stop)

3 nights Orvieto( on day city and one day rent car and drive to Assisi for the day)

2 nights Matera ( drive there with car rented previous day (Hertz I can drop in Bari-) enjoy one day in the city)

3 nights Locorotondo or Alberobello ( visit Locorotondo, Alberobello and Cisternino those two days)

3 nights Polignano a Mare (boat trip and enjoy looking at the sea and maybe cold plunge swimming, not sure about second day)

We are mid 50s have driven in the Dolomites a couple years ago and have driven in New Zealand and Scotland this year. The driving isn't our issue (well haven't encountered ZTL's before) the parking ( or lack there of it) drives us crazy. We also wanted to do less changing rooms and still enjoy the area. We like history, architecture and scenery, I don't anticipate hiking this trip.

  1. I am not sure about day trip to Assisi, as it is 3 hours driving but I really do not want to do a 1 night stop. Is there another choice for a day trip much closer?

  2. A.-Or stay only 2 nights Orvieto and then stop along the way to Matera overnight to break up the drive ( 6 hours which I assume will be 8-9 with stops)? B.-Or maybe not rent car in Orvieto, take train to Rome and then take train to Bari next day, C.- Or take train Orvieto to Bari in one day and sleep in Bari then train to/from Matera for 2 nights and not get car until after Matera? I want to do what is easier and less stress. Train strikes and break downs have gotten us before in Italy and Switzerland.

  3. Second full day staying Polignano a Mare- suggestions?

Thank you for any suggestions, I have read RS books from the library ( Spain and Sicily were also contenders for this trip) and many trip reports on Puglia, thanks for any additional help

Posted by
17161 posts

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.

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