When in Tuscany: Castles, Wine, and Kids in Pools (Not Always in That Order)
- Little Luxe Family Travel
- Jun 3
- 4 min read
A friend recently texted me asking for winery recs in Tuscany—and that’s when I realized: I’ve been hoarding this Tuscan gem of a trip like a secret vintage Brunello. It’s time to spill the (olive) oil.
So, let’s rewind to when I first started planning our week in Tuscany. I was excited, Pinterest boards were popping, but then... WHO KNEW Tuscany was so massive? I blinked and suddenly needed a geography degree and a sommelier certificate. I knew we needed this leg of our Italian journey to be special—read: slower pace, more wine, fewer Roman ruins. So, we split our week into three magical stays: Montalcino, Radda in Chianti, and just outside Florence. And yes, there was wine. And castles. And yes, the kids were with us. Here's how it went down.
Pit Stop in Orvieto – Because Road Trips Need Pastries
We picked up our rental car in Rome (pray for us) and headed north. But first, a detour to the hilltop town of Orvieto because sitting in traffic with kids = questionable life choice. Instead, we stretched our legs, visited the stunning Duomo di Orvieto (because if you’ve seen one church, you’ve seen... none of them, actually—they're all gorgeous), grabbed lunch at Il Dialogo, and did a little window shopping. Highly recommend. A+ for views and pastry-fueled patience from our children.
Montalcino – We Stayed in a Castle. Repeat: A. Castle.
Our first hotel? Oh, just 🔗Castello di Velona, a literal 5-star castle with thermal volcanic waters and drop-dead-gorgeous views. When we arrived, they greeted us with a bottle of wine—which we enjoyed poolside while the kids went full aquatic in the indoor and outdoor pools. Talk about balance.
Fun fact: The thermal pools are filled with mineral-rich water drawn from 250 meters underground. Translation: your skin glows, your stress evaporates, and your kids are too busy splashing to complain about anything. Win-win-win.
We dined via room service (parents of the year!) and called it an early night in our castle suite. I still can’t get over typing that.
Wine, Cheese & That Steak We Still Dream About
The next morning, after a Nutella-sticky breakfast, we headed to our first winery: Casanova di Neri, a small boutique winery with spectacular reds and olive oil. The kids enjoyed running around, and we enjoyed pretending we were wine connoisseurs.
Later, we ventured into the charming village of Sant’Angelo in Colle and stumbled upon Trattoria Il Pozzo—and OH. MY. FLORENTINE STEAK. This was the best meal of the trip. Family-owned, friendly, fabulous pasta, and yes—my husband bought a t-shirt. They were employee shirts but he had to have one!
Banfi & Dinosaur Bones, Naturally
Next day: Banfi Winery—the big, bold, beautiful one. We did the full tour, followed by a wine lunch that I still daydream about. Our son joined the grown-up tasting menu and left a ravioli connoisseur. Highlights included deep-fried buffalo mozzarella, 2018 Brunello and an unexpected side of dinosaur bone history (yes, really—they found fossils on the property). If that’s not kid-friendly wine tasting, I don’t know what is.
We wrapped up the day ringing the bell at the Fortress of Montalcino and catching the chef’s kiss of all Tuscan sunsets. Cue cinematic goodbye to Montalcino.
Cheese, Goats, and Our Very Own Nun House
On the road again, we stopped for a farm-to-table lunch at Podere Il Casale. We fed goats, learned how to make cheese, and yes—ate more cheese. Perfect lunch detour.
Next stop:🔗Pieve Aldina- Fontanelle in Radda in Chianti, a newly opened hotel that used to be a nun’s house. Our suite was chef’s kiss for families: two bedrooms, two bathrooms, a kitchen, and a porch where I briefly considered moving in permanently. The grounds were beautiful, the breakfast peaceful, and the pool cold—but the kids still jumped in. Because kids.
Horses, Wineries & "Wait… We've Been Here Before?"
We didn’t plan to visit Castello di Albola, but the hotel staff recommended it and WOW. We opted for a wine-paired lunch instead of a tour (best decision), and our waiter surprised us with a private walk-through of the historic grounds. Turns out we’d stayed at their sister property, Barboursville, in Virginia the year before. Small wine world!
Then off to Castelnuovo Berardenga for some horseback riding with panoramic Tuscan views. The kids LOVED it and we pretended we weren’t nervous about them riding solo. (They were fine. I needed wine.)
Final Stop: A Villa Fit for a Luxe Family Farewell
On our way to our final stop, we made one last detour at Antinori nel Chianti Classico, which looks like a spaceship landed in a vineyard—in the best possible way. This modern winery is a total architectural stunner and one of the most educational stops we made. Book early—it sells out! If you can’t get a tour, at least grab lunch at their gorgeous restaurant.
We ended our Tuscany adventure just outside Florence at 🔗Villa Le Calvane, and let me tell you—it was the perfect finale. Perched on a hilltop with views for miles, the hotel has a rich history (original church site from the 1300s!) and a family suite that felt straight out of a Nancy Meyers movie.
Breakfast? Amazing. Pool? Divine. Food? So good we ate at the hotel twice. We took a day trip into Florence, visited the famed wine windows (yes, literal windows that once served wine during plagues—very on brand), and then came back to our villa for a slow, delicious final night. Of all the places we have stayed, this hotel is talked about as on our our favorites.
Tuscany, You Had Me at "Thermal Pool"
Tuscany was everything we wanted: slower pace, jaw-dropping scenery, incredible food and wine, and a surprising number of kid-friendly moments. Whether you’re castle-hopping, sipping Brunello, or just letting your kids run wild through vineyards while you pretend not to panic near expensive glassware, it’s a dreamy family escape.
Next stop: the Amalfi Coast. But first—espresso. Lots of it.
Comments