There’s a particular kind of magic in Tuscany that never really lets go of you. I first felt it years ago when I studied abroad in Montepulciano, and now, decades later, I’m returning with my husband and children in tow to trace the cobblestones of my youth, introduce my kids to Renaissance beauty, and soak up the slow, golden rhythm of Italian life together.
This is Part 1 of our family’s September 2025 journey through Florence and Montepulciano—two towns that hold very different but equally important pieces of my heart.
Day 1–3: Florence – The Birth of the Renaissance
Base Camp: Alba Palace Hotel
The boys landed in Florence and met me at the train station (I’d already been in Tuscany for a week for a writer’s retreat) and together, we checked into the Alba Palace Hotel, a charming, family-friendly property tucked into the historic Santa Maria Novella neighborhood. The location was ideal: walkable to major landmarks but just far enough from the hustle to breathe. Our quad room was plenty spacious enough for the four of us and included breakfast each morning, which quickly became a favorite family ritual: espresso and cornetti for the grown-ups, scrambled eggs, meats and cheeses and Nutella everything for the kids.
Art, Architecture, and Awe
Day 2 began bright and early with a Florence Wonders walking tour, including skip-the-line visits to the Accademia and Uffizi Galleries. I’ll admit, I was a little nervous about how the kids would do with nearly six hours of art and architecture, but to my delight, they were captivated.
We started at the Accademia Gallery, where the sight of Michelangelo’s David in person brought audible gasps from everyone in the group. It’s hard to describe how this sculpture, so familiar in textbooks, transforms when you see it towering in front of you, perfectly lit, impossibly lifelike.
After a quick break for lunch featuring some of Florence’s most delicious sandwiches at Al Antico Vinao, we met up with another guide at the Uffizi Gallery. The kids loved the Medusa shield by Caravaggio, and in the same Caravaggio room, my eyes couldn’t leave Artemisia Gentileschi’s masterpiece, Judith Slaying Holofernes. Oscar and I also lingered in the Botticelli rooms, completely drawn in by Primavera and The Birth of Venus. Florence has a way of making even casual art lovers feel reverent.
Hands-On History
Day three brought more hands-on experiences. We started the day at the Galileo Museum, which is packed with early scientific instruments and fascinating models of Leonardo da Vinci’s inventions. It was a nice balance to the fine arts-heavy itinerary and gave our tech-curious boys to nerd out over.
Later that afternoon, we joined a Florence Cathedral tour of Santa Maria del Fiore (in English, translated to Saint Maria of the Flowers) including access to Brunelleschi’s Dome. I won’t sugarcoat it: the climb to the top is very steep and narrow, but absolutely worth it for the sweeping 360-degree view of Florence.
That evening, with tired legs and full hearts, we had dinner at a family-owned trattoria on the south side of the Arno called Trattoria Sabatino, where the line outside told us everything we needed to know about the delicious food inside.
Day 4: Florence to Montepulciano – A Scenic Shift
On Day four, we boarded a reserved train from Florence to my beloved Montepulciano, connecting briefly in Siena. The journey took about three hours total, and I can honestly say it was one of the most peaceful parts of our trip. Tuscan hills rolled past the windows like an old film reel—vineyards, stone farmhouses, and sunflower fields still clinging to the last few weeks of summer.
Arriving in Montepulciano felt like a homecoming for me. As we stepped into town, past the stone walls and toward the steep, winding streets, memories rushed back in waves: the first time I stood in Piazza Grande, the sound of church bells, the scent of warm bread and aging wine.
We arrived just after lunchtime, so I promptly took them to Caffe Poliziano for lunch, where we ate meats, cheeses, and pasta overlooking the Val d’Orchiana. Afterwards, we leisurely walked through the city’s streets until it was time to check into our Airbnb, which was just a few blocks away.
After checking into our Airbnb, we spent the rest of the day walking around and reacquainting ourselves with the rhythm of small-town life. We visited the fortezza where Kennesaw State University holds their study abroad classes, and I pointed out some of my favorite local shops.
That night, we are dinner at one of my favorite local places, Ristorante Godimento Divino, a family-owned place tucked away just a short walk from our new apartment. We ordered a true Florentine steak, complete with roasted potatoes and fresh grilled vegetables, and it was absolutely delicious.
Day 5: Slow Travel, the Tuscan Way
There are no scheduled tours or transfers on Day five, just us and Montepulciano. And honestly? That’s exactly what we needed. We wandered through the Corso, stopped for espressos and breakfast at Caffe Avignonessi, and admired the ceiling frescos. We visited Conad, the local grocery store, so the boys could explore what an Italian grocery store was like. We also went into Chiesa di Sant’Agostino, a beautiful church located directly across from the iconic Torre di Pulcinella, and marveled at the inside. Afterwards, the boys took a detour into the Torture Museum (I’d been, so I stayed at the Airbnb and caught up on some work), then we took them to see my first apartment, located at the foot of a gorgeous overlook spot off Vicolo della Mura.
We stopped in and grabbed sandwiches for lunch at Birrificio di Montepulciano, a great spot for a sandwich and local craft beers, then continued to explore more of the city’s main streets and side alleys.
Finally, we met a local expat family at Pizzeria e cucina da Linda for dinner, and the boys were more than happy to have an opportunity to stuff their faces with meats, cheeses, and their favorite Italian food, pizza.
After dinner, we walked through Giardino di Poggiofanti, the park just outside the ancient city walls, and slowly made our way back to the Airbnb.
The next morning, we had a mid-morning train to catch to Rome, so we revisited Caffe Poliziano for a quick breakfast before snagging a taxi to the train station.
Looking Ahead
In Part 2 of this series, I’ll share the second leg of our journey, our arrival in Rome, an evening tuk tuk tour through the Eternal City, and our day trip to Pompeii and Sorrento. But for now, I’m content to stay here, in my mind at least, in this quiet hilltop town that feels as close to a second home as any place I’ve ever been.
If you’re planning a trip to Tuscany with your family, here’s my advice: Don’t rush. Listen to the Italians when they say, “Piano, piano” or: “slowly, slowly.”
Let yourself linger. Let your kids discover the magic. And if you’re lucky, you’ll rediscover some magic of your own.
