Tuscany: Full Itinerary

Ten Days in Tuscany

Who wants a family-friendly itinerary laid out for them?? This is the bare bones version, but if you’re planning a trip and would rather not lift a finger, please reach out to me for the over-compulsive hour-by-hour version. Please note that every day should include a pre-dinner Negroni!

Day 1

Arrive at Podere Spedalone and settle into your room(s), let them know you’ll eat dinner with them, and take a dip in the pool.

Days 2-4

Visit Montepulciano, San Gimignano, Montalcino, Pienza, and some wineries. You can plan which places to visit in one day based on how much driving you want to do, when you schedule winery appointments, and how relaxed or ambitious you want to be. You can also take a cooking class at Podere Spedalone, which I wish we had done and would love to do next time!

Days 5-6

Visit Siena. On the way to Florence, stop by Antinori Nel Chianti Classico.


The architecturally impressive, highly commercial Antinori nel Chianti Classico Estate is between Siena and Florence. You do not need an appointment to visit the winery or stop in the tasting room. However, you should plan ahead and make a reservation if you want to take a tour or eat at the beautiful rooftop restaurant. The food and wine flights looked good, the setting was lovely, and you’re unlikely to get a table as a walk-in. The estate is extremely child friendly, with lifts, high chairs, changing tables and room to run around.


I also have a really fun tip! If you have a stroller and want to go up to the roof, the staff will escort you to a special elevator, which goes right through the winery’s tour-only barrel room. The barrel room is very cool, and you don’t have to try dragging your toddlers through the whole formal tour. Maybe you can also ask for the elevator to the roof without an obvious need for it.

You definitely won’t get the personalised attention, nor the bang for your buck, that you can find at less commercial wineries. I do not recommend the tasting room, where the pours are brutally small and expensive, and the servers didn’t give us a second glance, let alone any information about our tiny (admittedly delicious) taste. But all in all, it’s an impressive stop.

Days 7-8

Visit Florence.


Day 9

If you are up for a beautiful, winding countryside drive to a super-local foodie heaven, you’ve got to make a reservation at Albergo Cerfogli! It’s about 2.5 hours from Florence, but worked for us because we were flying out of the Bologna airport the next day.


Along the drive between Florence and Albergo Cerfogli

This restaurant is a truffle heaven. We told the chef we would do his tasting menu, and trusted him to create our dinners. We were not charged for the children, and there is no corkage fee if you prefer to open the bottles you’ve bought.


The town is only one (super cute) street, but there is a little playroom at the inn, and the kids loved the toys. We were able to feed them dinner, put them to bed and then come downstairs for our own feast. As you know, I’m a big fan of that routine. The room was huge, with two bedrooms, and cribs are available. Breakfast is included.


Acquaria, Italy

One Last Winery…


On our way to the Bologna airport, we decided to stop by the Manaresi Wine Estate because we had really enjoyed their Flora Italica Barbera with dinner in Bologna. I called them and asked if we could visit, and even though they were in the middle of their harvest, they accommodated us. How incredible is this machine that separates the grapes from the sticks??

That was our last hurrah before heading to the airport!


I’ve skipped a couple of towns where we stopped for lunch and visited ancient ruins, either because we didn’t think they were worth the detour, or because our rental car almost died trying. But here are some pictures, and if you have questions, I’m more than happy to answer!


Ponte d’Olina


Castellina in Chianti






Outtake: When the kids look cute but the parents are annoyed at the stranger in the background!

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