Last minute trip to Italy



My girlfriend and I found a great deal to Milan and we will be coming in less than month and I am overwhelmed by all the information I’ve read. Ever since we saw the movie Under the Tuscan Sun we have been dying to go. We would like to see some history and arts but we are more about the food, wine, meeting great people and enjoying the beauty of Italy.

We fly into Milan on the 14th and fly out on the 23rd. Originally, we were going to take the train all around, stopping a day in Genoa, Pisa, Bologna, 2 days in Parma and 3 days in Florence but after reading through many forums that seems a bit too aggressive. I don’t know much about Genoa and Bologna but chose those cities as they are along the path to and from Milan. And we wanted to stop in Parma for the prosciutto and cheese. We would really love some assistance on planning our itinerary.

1. Should we just skip those spots and go straight to Florence?
2. Once in Florence, should we keep that as our base and travel out to Pisa, Volterra, the Chianti region, etc? Or should we find a base somewhere else and travel to Florence? What cities do you recommend?
3. I read the best way to see Tuscany is to drive but after reading about the ZTL zones and no parking areas I’m worried that we’ll end up paying a lot for fines and tickets. Also, we would like to do wines tastings and not worry about drinking and driving? What is the best way to get around to see what we want while staying safe and not to costly?
4. Finally, any suggestions on places to stay where we will get a great experience.

I hope this isn’t asking too much. This trip was so last minute I feel like I don’t have enough time to make the right decisions. Any assistance would be so great! Thank you!


Well-known member

I suggest you divide you stay into two areas, Florence city center (from here you can visit all of Florence and train it to Bologna (30 min) or Pisa (60 min) for a day or afternoon) and then move yourself into the countryside and pick up a car for your travels in the Tuscany.

Look at a place like Borgo Argenina
Which puts you in a great position for visiting Chianti, Siena and … even Cortona! Anything in the Gaiole
Castelnuovo Berardenga would be great for a stop in the vineyards and olive groves.

I would go directly to Florence check in and do a first day just soaking in the atmosphere.
15: Next day a museum & church (Accademia & Duomo with all that is connected to it)
16: Bologna/Parma
17: more history visits in Florence - (Uffizi, Palazzo Vecchio and maybe visit Santa Croce)
18: Pisa and Lucca
19: Late departure Florence for leisurely itin in Chianti
20: Arezzo / Cortona
21: Downtime in the morning - maybe a hike near your accommodations or check out a local market or arrange for a wine tasting & then Siena in the afternoon
22: Montepulciano / Pienza (views that rival Cortona ;-) )
23: Downtime in the morning depending on your flight out you may need to make your way back to Milan to day??
24: back to Milan for your flight

Buon Viaggio,
Donna Denise


Thank you. Now would I rent the car in Florence or in Chianti? Is it pretty easy driving in Tuscany? Is there anything I should know in advance about driving the area?


Well-known member
car rental


Rent your car out of Florence.

Personally I find driving in Tuscany to be fairly easy - and extremely beautiful. The Tuscan drivers fall into two categories..."going some place with determination and ...speed"... or your Sunday Drivers. But in either case I have found the drivers to be courteous (enough :eek:) and the roads (at least the ones suggested in many of our intins) are easy to navigate.

Donna Denise