I had wanted to see Tuscany long before this trip to Italy. The idea was almost irresistible: hillside towns, quiet countryside, wine and food, all within reach of Florence. When we finally made it there in April 2026, I knew I didn't want the experience to become a race between stops.
So we booked a private day with a driver and guide, Carlos, and made time for four very different places: San Gimignano, Siena, Chianti and Pisa.
It was one of those rare travel days that exceeded what I had imagined. Not because every stop was an undiscovered secret, but because we could decide how much time to give the experiences that actually mattered to us.
Why the private tour was worth the splurge
Private touring is not how we travel everywhere. Sometimes walking through a city, using trains or joining a small group is perfectly adequate. But Tuscany's appeal, to me, is as much in the space between its towns as in the attractions themselves.
I found Carlos through a Florence tour group. He proved to be an excellent companion and guide, and we never felt that the day was being measured against a rigid timetable. We could enjoy the views, linger over things that interested us and keep moving when we were ready.
It was also an intentional splurge. We had used three Hilton free-night certificates for our Florence hotel stay, leaving more of our trip budget available for a private experience. That is the kind of tradeoff I value: not chasing points for their own sake, but using the savings to do something memorable.
Four stops that deserved more than a checklist
San Gimignano looked the part immediately: rooftops, stone streets and hills spreading out beyond town. It was the sort of place where even an ordinary view made me want to stop for another photograph. We also found time for gelato, including Gelateria Dondoli.
Siena was even better for us. Its architecture and skyline made it feel like more than a quick sightseeing stop, and I found myself enjoying the simple act of walking around. We came home with Italian dressings and sauces from Nino & Friends, which is a more useful reminder of a day than another generic souvenir.
Chianti was a different pace again. Our tasting at Corbucci was one of the highlights of the entire day. The setting, the attention to the experience and the chance to actually slow down over the tasting made it special. We liked the wines enough to order a selection for delivery to Canada.
Pisa was pretty and absolutely worth seeing as part of the route, although Siena made the stronger impression on me. And that is precisely why I liked having a private day: we didn't need to pretend every stop deserved identical attention.
One lesson arrived after we got home
The only part of the day that became complicated was the wine shipment.
At the tasting, we were assured there would be no import charges when our order reached Canada. I was sceptical, and unfortunately I had reason to be. When the delivery arrived, the customs bill was almost as much as the wine itself.
I contacted Corbucci and, after some back and forth, they acknowledged the mistaken information and agreed to cover the customs duty. That didn't remove all the administrative work or the extra expenses: I still had to deal with provincial and federal payment requirements in person.
The wine made it home, and the tasting is still a lovely memory. But my takeaway is straightforward: if you're shipping wine internationally, don't treat a verbal assurance about taxes or import charges as the final word. Check the rules for your own destination before ordering.
What I would do differently
Very little.
I would happily repeat a private Tuscany day, perhaps leaving extra time for whichever town captured our interest most. It wasn't a cheap way to see the region, and I wouldn't present it as the only sensible one. But for us, the freedom to travel at our own pace justified the expense.
Florence gave us the base for the trip. Tuscany gave us a day of views, food and conversations that felt entirely our own. If I were planning that part of Italy again, I would protect time for Tuscany before adding another crowded city attraction.
The best part wasn't fitting four stops into a day. It was not feeling rushed at any of them.