Itinerary help- based in Chianti


New member
Hi there!
My husband and I will be traveling to Tuscany this May/June with my parents to celebrate my mom's 60th birthday! First time in Tuscany! We will be based out of Chianti for most of our trip.
So far, our itinerary is:
1. Fly into Pisa, take the train to Cinque Terre and spend 3 nights in the Cinque Terre.
2. Take the train from Monterosso Al Mare to Pisa where we will pick up our rental car to head to our next home base of Chianti where we will spend 7 nights.

We will be in our B&B in Chianti for 7 nights and the plan is to take the rental car and do day trips from our home base each day. We will have 7 full days to explore the region. There are so many places to visit that I am having a hard time narrowing and planning each day trip. Any must see recommendations would be appreciated!

So far I am thinking:

1. If we pick up our rental car in the AM from Pisa right after leaving the Cinque Terre, is it doable to visit Pisa and Lucca before making our way to our Airbnb in Chianti? Too much for one day? It seems to be on our way. I definitely want to explore Lucca as I have heard great things!

Other places I am thinking for a day trip:

1. val d'orcia --- advice? must see towns?
2. Florence (maybe we will go two days)
3. Stay in Chianti a day and explore/wine taste

I am open to other day trips as well and would love some advice. Thank you SO MUCH!


The Tuscan Expert ;-)
Staff member
Ciao julsat1 and welcome to the forum!

Sounds like you're already way ahead in planning this fabulous trip, let's see if we can help sort out the questions you have now.

With your 7 days, I suggest you make a schedule but remain flexible, so that you can take more time and return to a place if you want to explore it more rather than try to fit everything in you plan on now. For example, spending an extra half day somewhere if you

1. It does make sense to visit Pisa and Lucca since you're in the area before heading to Chianti. The only concern I have is luggage -- you don't want to leave it where it can be seen in a parked car while you go sight seeing.
So one possibility is to take the train from CT and stop in Lucca first, leave your luggage at a deposit near the train station while you're there for the morning, then pick it up and continue on to Pisa, do the same in Pisa before picking up the car and continuing on to Chianti. You could divide the day like that, and it is doable.... you might not get to see or do everything you should in either town, but if you want to return and spend more time, let's say in Lucca to bike around the walls during your week's stay, you could!

2. Val d'Orcia for sure! Visit Montalcino (and nearby Abbey of Sant'Antimo), San Quirico, Pienza and Montepulciano. The drive in between is also gorgeous! You could do return another day as well, to also see/visit the hot springs in either Bagni Vignoni or San Filippo: take a look here

3. Florence - again a definite yes! I suggest a day trip for sure, you can drive to Florence and park in Galluzzo or at Villa Costanza and take tram/bus into the center, that way you don't worry about the ZTL, which is off limits, nor about parking.
Here's a one day itinerary:
and a two day itinerary:

4. Since you're in Chianti, it's a given you'll take time to visit the towns nearby, here are some you should not miss:
- San Gimignano
- San Donato in Poggio
- Greve in Chianti
- Castellina in Chianti
- Panzano in Chianti
- Radda in Chianti and Gaiole in Chianti could be done in one day.... there are a lot of wine estates across the entire region so you will have to decide when and where to stop at ;-).

5. Other day trips:
- SIENA!!! A whole day here, at the very least, so you can climb the Torre del Mangia and see the inside of the Palazzo Comunale and the inside of the Duomo! Don't miss these sights, in addition to just enjoying walking over the town and Piazza del Campo.
- Arezzo: if you have a chance, you should make a stop here as well, to enjoy the Piazza Grande and at the very least the church of San Francesco to see Piero della Francesca's frescoes in the main altar.

Hope I've given you more ideas - but again, remain flexible with your time so that you're not rushing and enjoy what you're doing ;-). Live in the moment!