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5 days in Tuscany/Umbria--suggestions?

I am taking my mother to Italy again this August! (In our past two trips, we've been to Rome/Sorrento and Lake Como/Venice/Ravenna.) We got a great airfare this time (round-trip under $700!), but coordinating our two schedules only gives us 7 days on the ground in Italy. We are flying in/out of FCO and want to spend the last two days around Rome (one to visit Ostia Antica), so we will have 5 days for north of Rome (Tuscany/Umbria/Florence). I visited Florence, Pisa, and the Cinque Terre back in 2001 as a backpacker, but my mother has never been anywhere in the Tuscany/Umbria/Florence regions. We love nature, history, and walking.

I have read Rick Steves Italy 2014 & 2015 but still have some questions and would love some suggestions:

  • With only 5 days, I would like to visit Siena, Lucca, and at least one more place--not sure where.
  • I love public transportation in Europe, but it looks like seeing a lot of Tuscany/Umbria is hard by public transit. My mother would like to rent a car, even for a day or two, but I would rather not. Is there a two-ish day driving route with easy pick-up/drop-off of a rental car that would allow us to see a lot but avoiding city traffic/driving?
  • We prefer two-night stays to limit hauling our bags around. If we don't rent a car, is Florence the best city to home-base in?
  • Any recommendations of day-tours to smaller towns from Florence/Siena/Assisi?
Posted by
7175 posts

Why not something like this ...
Day 1 Train from Rome to Assisi (via Foligno)
Day 2 Pick up rental car (possibly in Perugia)
Drive to Siena via Montepulciano & Montalcino (or Cortona & Arezzo)
Day 3 Drive to Pisa via San Gimignano & Lucca - return rental car
Day 4 Train to Florence after morning in Pisa
Day 5 Full day in Florence
Day 6 Train to Rome

Posted by
15799 posts

Much as I enjoyed an overnight stay in Assisi, it is not easy to get to - regional trains, transfers, then a bus or taxi from the station up to the town. With only 5 days, I'd skip it. From FCO, take the Leonardo Express to Termini and get a fast train to Florence. From Florence, you can day trip to Siena and San Gimignano by bus (not on the same day, though). You can take the train to Pisa for a 1/2 day trip. You can day trip to Lucca, but I haven't been, so don't know if it's bus or train. You can day trip by train to Bologna for a day. From Florence, it's about 2 hours by train to Orvieto for an overnight, then another 2 hours by train to Rome. Florence is probably the best base without a car because of the fast, frequent trains to/from Rome. Also, the main (Santa Novella) train station is right in the historic center. You can stay in the center (hotels at every price/star level) and be within a 5-10 minute walk of the train station, for easy access to buses and trains, and still a 5-10 minute walk to sights there and restaurants for dinner at the end of a day trip.

Or you can rent a car in Florence, stay in an agriturismo visit more towns in Tuscany.

Posted by
11613 posts

I love Siena and Assisi, some hotels have onsite parking. From Siena you can get to Montepulciano or Montalcino by car or bus, car is more convenient. Pienza, Arezzo and other small towns are nearby.

If you base in Firenze, it's easy to get to Siena and Lucca/Pisa by bus or train for day trips. Siena can take a full day, even better for a night or two. Pistons is also near Firenze. For a shorter trip, Fiesole is only a local bus ride away.

Posted by
1825 posts

I am writing this from our hotel in Rome. We just came from Orvieto which was wonderful. Easy to navigate, beautiful views and only an hour by train from Rome. We had a car and drove from Siena with an overnight in Montepulciano. Wish we would have stayed two nights in Montepulciano and the three we had in Siena were perfect. Driving Chianti and Tuscany is more beautiful than pictures show and the food was inexpensive and we never had a bad meal.

Posted by
18 posts

I just got back from a 11 day stay in Italy, we had 2 days in Rome on our own and then took a 3 night/4 day tour Tuscany/Cinque Terre Tour from Rome/Viator Tour which actually turned out to be given through an Italian tour company and the tour was excellent. I chose this tour because we wanted to see alot of Tuscany but we didn't want to drive.. We had a great time, the food was wonderful, as was the tour guide Maria, we saw many Tuscan towns and were able to fit in 3 wineries. We didn't feel rushed, saw lots of beautiful scenery and loved the boat ride from a La Spezia to the Cinque Terre stopping at Vernazza, Riomaggoirre and Monterossa. The tour runs from Sunday morning through Wednesday night. If you would like more specific information please feel free to send me a private message. When we came back from the tour we spent the last 5 days around Rome and also did 2 day trips by regional train to Orvieto and Castel Gandolfo, both were easy to get to and well worth a side trip. So my trip was a nice mix of on our own time and tour time.

Posted by
233 posts

Thank you so much to everyone for the replies! I'm still investigating all the information you shared. I looked at the tour mentioned, but we arrive on a Tuesday, so no luck. There are took many choices for only 5 days :) Thanks again!

Posted by
26 posts

As I'm sure you know, Italy can be exhausting. I would definitely go to Siena, but not just as a day trip. I stayed there for almost a month 2 years ago. I would see large day trip crowds in the morning in afternoon all leaving by dinner time. At night it was way more serene. Consider staying the night in Siena for a very peaceful and relaxing small-city feel. It's so easy to escape the city walls in Siena and walk alongside farms and vineyards. At night you can feel extremely safe strolling the tiny streets. (I say this as a female solo 20-something traveler). The museums are fabulous and not overcrowded (like Rome or Florence).