Using San Gimignano as Our Home Base for the Week
After a few bustling days in Rome (you can read about our stay here), we slowed things down with a week in Tuscany—and it was exactly what we needed. We stayed just outside of San Gimignano at Villa Binetti, a peaceful property with views for days and plenty of space for the kids to run around. San Gimignano made the perfect middle point between Siena and Florence, and it allowed us to explore the region without spending hours in the car each day. With a baby and three big kids in tow, I try to plan one main outing or activity per day, then leave space for naps, swims, and slow moments. It’s not about seeing it all—it’s about enjoying what we do see (and keeping everyone sane).
Villa Life: Slow Mornings, Grocery Runs & Poolside Afternoons
One of the best parts of our stay in Tuscany was simply settling into a slower rhythm at the villa. With three big kids and a baby, having a full kitchen and a comfortable home base made all the difference. We stocked up on groceries early in the week at the Coop—a great local supermarket with everything from fresh produce and cheeses to coffee, pasta, and picnic snacks. Being able to make breakfast each morning (and sip coffee in peace while the kids played in the yard) set the tone for more relaxed, unhurried days.
Most mornings, we’d head out on a small adventure, knowing we could return to the villa for nap time, or a dip in the pool. The property itself had plenty of space to run around, shady spots to read a book, and loungers to stretch out and soak in the Tuscan sunshine. The kids lived in their swimsuits and rotated between pool time, card games, and chasing each other around the lawn.
We also made use of the outdoor dining areas and had long, simple dinners al fresco—charcuterie boards, pasta from the Coop, and local wine. One of the biggest highlights was the night we had a local chef come to the house (arranged by our property manager). He brought everything—ingredients, wine, charm—and created a full, multi-course Tuscan meal while we relaxed and watched the sunset. For families traveling with littles, this was such a treat.
swim // pareo // hat // dress sold out (similar here) // baby romper
Day Trip to Siena
One morning we drove to nearby Siena (about 45 minutes away) and spent a few hours soaking in the history. Even with a bit of a sick kiddo that day, we loved wandering the streets and stopping to admire the stunning interior of the Siena Cathedral—honestly, one of the most jaw-dropping churches I’ve ever seen. The striped marble, vaulted ceilings, and floor mosaics are all works of art. We also visited the Piazza del Campo, where the famous Palio horse race takes place.
For lunch, we tucked into Osteria Permalico—a cozy spot a bit off the main drag. Their lasagna was unbelievable, and the whole experience felt quiet and local. If you have more time in Siena, you could also visit the Torre del Mangia for sweeping views or the Santa Maria della Scala museum for a mix of art and history, but we kept things short and sweet.
Florence: A Day of Art, Views & Gelato
We only had one full day to explore Florence, but it truly made an impression. From incredible food to unforgettable views, this city packed a punch—even with kids in tow. We started with lunch at All’Antico Vinaio (yes, the hype is real—the sandwiches were enormous and delicious), then wandered through the historic center, taking in landmarks like the Duomo, Piazza della Signoria, and Ponte Vecchio.
Even if you don’t have time for the museums, there’s so much to absorb just walking the streets. We saw Michelangelo’s David (well, the replica in the square!), wrapped things up with what may have been our favorite gelato of the whole trip at Vivoli.
Florence is definitely a place you could spend several days exploring more deeply—but for our crew, one big outing was just right. We left with full hearts (and full bellies) and are already dreaming of coming back.
✨ You can read our full Florence guide here for all the details on where to eat, what to see, and what we’re saving for next time.
Afternoon Truffle Hunting Experience
One of the highlights of our time in Tuscany was truffle hunting with Truffle in Tuscany, run by a third-generation truffle hunter named Massimo. He took us through the woods near his property alongside his (very enthusiastic!) dogs, teaching us about the different types of truffles and the tradition behind it. Afterward, we sat down to an incredible truffle-filled meal in their kitchen—fresh pasta, eggs, and more. It was rustic, cozy, and absolutely delicious. Highly recommend booking in advance!
Exploring San Gimignano
Another morning we explored San Gimignano, a medieval hilltop town famous for its towers. We kept it low-key—just a stroll through the winding streets, a climb to the scenic viewpoints, and a relaxed lunch at La Mandragola, a lovely little spot tucked away with a garden terrace. I had the artichoke and truffle ravioli and am still dreaming about it.
We stopped by Gelateria Dondoli afterward for their award-winning gelato. It was good, but honestly? The hype may have set expectations a little too high. Still worth trying if you’re nearby—especially for the kids!
Tuscany gave us exactly what we were craving after the pace of the city—space to stretch out, room to breathe, and the chance to experience Italy in a slower, more grounded way. Having a home base near San Gimignano allowed us to explore just enough—Siena, Florence, truffle hunting in the hills—without feeling like we were constantly on the go. The villa gave our family the freedom to fall into a rhythm: relaxed mornings, one adventure a day, and poolside downtime in the afternoon. With three big kids and a baby, that balance made all the difference. We left feeling rested, connected, and full of memories that somehow feel both big and beautifully simple. Tuscany, we’ll be back.
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