Help in Planning a family Trip to Tuscany June--July 2019

Yes, you have way too many places for 1 week. I suggest you start by you and the kids watch some youtube videos on each of the places on your list, and let the kids be involved in the decision making. It will make life easier if they have input!

I don't know if you have driven in Italy before, but be aware each driver needs an International Driver's Permit. Available at any AAA office.

Gee, this sounds familiar. We did this same kind of trip in 2014. We stayed at Villa Arnilu (with pool,Google it) near San Gimignano and visited Pisa, 5 Terre (a long day trip but you could do Lucca pretty easily), Siena, and Volterra. We had been to Pienza but you could do that as well. Also, Monteriggioni is with in reach. We trained to Florence from Poggibonsi twice, easy trip. Lucca, an absolutely great town which I have visited many times, puts you a bit out for the southern Tuscan areas but it is doable also, Just a thought, most pools in Italy are cold, cold, cold. Too expensive to heat, but your kids swam anyway. All in all I like the San Gimignano area for your plan.

Good food and wine is found every were but try to go to the local places, rather than tourist places. That's hard in cities like San Gimi buy you can find them.

You will need a full day to drive to Lucca and Pisa, but you can see both in a day. Volterra is very close to San Gimignano so no worries there, half day, cool Etruscan stuff and beautiful alabaster. Take a day and go south to Siena, Pienza, stop and Monteriggioni on the way back for dinner. Spend one day at the villa relaxing, and with that run over to San Gimignano for dinner, lunch, or just to visit, have some gelato.

Don't miss. Campo Santo at Pisa, rebuilt after WWII. The tower in Lucca, towers and castle in San Gimi, lunch in the piazza in Siena, lunch or dinner in Pienza and the Pope's house. If you have time go up to Piazzale Michelangelo in Florence and get a wonderful overview of the city. You can buy groceries at PAM in Poggibonsi and cook at a villa. Lots of other things too, but you will have fun finding them all and talk about them for years to come.

Have a great trip.

Staying in the San Gimignano area will cut your travel times considerably.

As previously posted, along with the IDP, you need to read this and download their PDF file for signage and italys rules of the road. Not knowing these will result in some pretty hefty fines up to a year after returning home.

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Thanks for the input so far. Gordon, I like your thinking--so if we get an early start we can spend the morning and the afternoon and early evening in Lucca? Is Poggibonsi the train station closest to San Gimignano? I like the idea of being close to there to drop in at night after the day-trippers leave. I like the idea of heading down to Pienza and Siena as well. A lot to consider!

It is about 75 miles to Lucca. That is via the SiFi autostrada past Florence and then down the Arno River to Lucca. You can go cross country and it is only about 50 miles, but the roads are more windy. You might do both and see some of the sites/sights on the way to Lucca and return on the nicer roads. Or, you could even go through, or by, Pisa on the way as well. Lots of options. So yes, give your self some travel time but you could spend the day in Lucca. If you have time go up to Montecatini Alto, a cute little place between Florence and Lucca, above Montecatini Terme.

Yes, Poggibonsi is the train station closest. It is about 8 miles from San Gimignano. Yes, visiting the town after the day trippers is a very good idea, and don't miss the restaurants on the west side of town. Here is a restaurant suggestion CUM QUIBUS, in town. and try Fuoriluogo, on the west side as I remember, not the main part of town. Over where the locals hang out.

It is only about 25 miles to Siena, park in Santa Caterina Parcheggio and take the escalator to town. It is an easy trip to Siena. Pienza is a bit further, about 60 miles. And you go right by Montepulciano. Things are pretty close together around there so see as much as you can. You go by Monteriggioni on the autostrada between Poggibonsi and Siena.

Buon viaggio

Thanks for all the helpful info! I'm sure to make use of it. I have another question for the board--I notice my time in Tuscany overlaps with the Palio in Siena--is it really a crazy scene there on that day? As interesting as it sounds, I wonder if it would be easier to visit on a day leading up to it. Has anyone been there for it?

I have been to Siena. I've NOT been to il Palio.
That said, if I were in the area and it was being run during that time frame. I'd do all in my power to embrace it not avoid it.
It's a spectacle you're never going to see in your hometown or anywhere near there.

It might cost a little bit more. And it might be more crowded than usual, but It's a spectacle you're never going to see in your hometown or anywhere near there.

When I travel, I look for experiences I cannot get anyplace else. CHECK!
I spend my money on experiences rather than a fancy place to sleep. CHECK!

I rearranged my itinerary in 2017 so that I would be in Venice on my middle weekend rather than my first or last so I could experience Regata Storica, which has been going on for hundreds of years on the Grand Canal. There's no Grand Canal in my hometown or any place near it.

I would sign up for il Palio if it were in my power to.
I hope you'll consider it.

We were in Siena the day before the Palio, late June. It was so much fun and was a highlight of our extended family's trip to Tuscany. Parades in medieval costumes, all the neighborhood flags for sale, horses being exercised. Our whole family still have their different flags which are like silk scarves.
I love Lucca and spent four nights there. But it is so far west in Tuscany that it is not a good base for exploring other towns and villages except maybe Volterra. Be aware that there are paper plants outside of Lucca, not something I ever want to be near. We almost always have stayed in the Chianti region and find it perfect.

6 of us, 2 adults and 4 children ages 11--15

Just a little comment: you won't be renting a "car" with this many people. You will need a van that can handle all of them plus their luggage. You will need to park outside of locations in your list that are pedestrianized or restricted to locals, and walk or take public transit in. You do not want or need a car in Florence!

And yes, you'll need to narrow your day-trip list for a 1-week visit, and plan to spend the night before departure in the city you'll be flying from.

Believe me, I know all about minivans--it's what we always rent on vacation! And I was planning on taking the train to Florence. I'm looking to fly home from there, so the trip to the airport from a house near San Gimignano should be fine, no?