4/5 days in the Tuscany area


New member
Hey guys,

I am planning on spending 4-5 days in the Tuscany area, and could use some help planning the details. Right now we have a rough itinerary, but we are totally open to changes and suggestions. We’re in our late 20s, have no problem with a fast pace, and want to focus on enjoying the food and wine, seeing the major tourist points, and just overall relaxing.

We will be leaving from Milan with a car on a Saturday afternoon, and planned on going to Cinque Terre for the rest of the day and spend the night (any idea on specifically where?). On Sunday, we would leave the Cinque Terre area and drive through Pisa just to take a look at the tower, and make our way to Florence. We would spend that day in Florence doing some sightseeing and eating and stay the night there. The next day (Monday), we could take a day trip to the Chianti area to visit some wineries, and then come back and stay the night in Florence again. On Tuesday, we would drive down to Sienna to check out the town, and maybe hit some of the closer wine regions and spend the night. On Wednesday, we would drive down to Montepulciano for a day trip and check out more of the wine areas there, and then make our way back to Sienna for the night. On Thursday, we would leave the Tuscany area and head down to Rome.

Some concerns we have – In Florence, these ZTL zones seem pretty annoying. Where’s the best place to stay that is as close to the center of town that has easy/cheap parking outside of the ZTL? Or should we just get a hotel inside of the ZTL, park outside of it, and get a taxi to take us to the hotel with our bags? Also – should we stay in Florence and Sienna for two nights each, or should we base out of somewhere else that may be better or more convenient?

Any other suggestions are very welcome – feel free to suggest something completely different. Thanks.


The Tuscan Expert ;-)
Staff member
Ciao drdavidge,

The easiest of the Cinque Terre to visit with a car is Monterosso but at the same time it isn't the most characteristic, Vernazza and Manarola are. Since you want to see them quickly, I'd head to Monterosso and park there, take the train to the other towns. I'd spend the night in Monterosso, just since it will make it simpler to just drive out from there as well and leave time to visit Monterosso that Sunday morning.
Drive to Pisa, there are parking lots close to the Piazza dei Miracoli so you can park, go to the main square, see the monuments from the outside and then head on to Florence. I'd normally suggest spending more time visiting the monuments there but I understand the desire to see more places in your limited time.
So then Florence, 2 nights there.
Then Siena, 2 nights there.... your plans for day trips are fine, just remember to spend time in Florence and in Siena as well :D

If you don't mind being on the move each day, you could theoretically spend 1 night in Florence, 1 night in Chianti, 1 night in Siena, 1 night in Montepulciano... that way you don't backtrack.

If you'd prefer the convenience of staying in one place longer, and Tuscany is pretty small so that you could drive out every day in a different direction, you could stay somewhere more central, in Chianti for example. You could head there from Pisa and do a day trip to Florence, parking in Piazzale Michelangelo while you visit Florence and not worrying about the ZTL.

I'd suggest some of these places for this second scenario:

If you instead do choose to spend a night or two in Florence, I'd definitely recommend staying in a place that offers parking, one outside the ZTL would make it easier. Although if you do stay within the ZTL, you can drive in to drop off passengers and luggage and then drive back out to park. BUT make sure to have your hotel communicate your license plate to the authorities, otherwise you'll get a ticket in the mail several months later when you're back home.

Some suggestions in this case:

Hope these work as a start, let me know if you need more ideas! :)


New member
Thanks Lourdes. The plan has changed a little bit since I wrote this post up. It seems like I wouldn't really have enough time to get everything in with the time I have there, so I took Cinque Terre / Pisa out of the picture. Right now we have:

Saturday: Florence @ Hotel Principe
Sunday-Tuesday: Chianti (Not sure where yet)
Tuesday-Thursday: Montepulciano @ Il Palazzo dei Diavoli

Was planning on hitting Sienna on Tuesday during the drive from Chianti to Montepulciano.

How's this sound? Any particular suggestions on where to in Chianti location wise, aside from the ones you already sent? Greve? (I will take a look at those).

How about particular plans during the day for wine tasting, eating, and relaxing?

Thanks again!


The Tuscan Expert ;-)
Staff member
Greve and wine tasting in Chianti and Montepulciano


Yes, I was trying to make your other itinerary work but it did seem you would be running quite a bit to get from one place from another. Italy is best enjoyed if you go with the flow, so slow is better! :D

The recommendations for Chianti still stand, also because they are all in wine country with wineries nearby that you can visit, touring the cellars, wine tasting and many offer light lunches as well. Except for Malaspina which is in the center of the medieval hilltop town of San Donato in Poggio, all of the others are in the countryside and have a pool, Poggiale also has a spa. So wonderful opportunity for relaxing. As far as Greve, the ones I personally know are for weekly rentals.... but there are certainly some great options from farmhouses as B&B/hotels for shorter stays - take a look at the possibilities in Greve and nearby as well as these two in particular: Da Verrazzano in the market square in Greve and Il Casello between Greve and Panzano (this second one looks gorgeous and has great reviews).

I don't generally offer specific recommendations on wineries/cellars/tastings because many have wine shops right along the main roads so you can just stop and do tastings, some require reservations for either tours or tastings and then they all have days when they are closed... too difficult to keep up! So my best recommendation is really to just ask where you're staying at for the wineries you can visit nearby: you are in wine country both in Chianti and in Montepulciano, you cannot go wrong! :D
In the smaller hilltop towns in Chianti, such as Radda and Greve, the tourist offices also will show you on a map and tell you which ones are open, for example if it's a Sunday... if you just want to drive around and pick one! :)


New member
Thanks again. I think we're down to a few hotels in the main towns.. I was thinking it might be better to stay in the towns for convenience? It's either the Relais Fattoria Valle in Greve or the Relais Vignale in Chianti. Any thoughts on those two locations?


The Tuscan Expert ;-)
Staff member
Yes, staying in the town or just outside is convenient, as then you can choose to walk there for an evening stroll or meal without need of the car.... I see both are relatively close to both towns. I checked out their listings - Relais Fattoria Valle is actually just outside of Panzano and not Greve (according to the map and address, not their description) - while the Relais Vignale is actually in Radda, right outside the city gate and since Radda is really small, you're practically in the town.
I think either is a great choice, maybe if you want to be in town the one in Radda is better. Both have magnificent views of Chianti and vineyards, so it is hard to decide on any other factor ;) both have parking, both are good bases for moving around the area. If I had to choose for my own stay, I'd likely go with Vignale ;-)