Tuscany is one of those places that never really leaves you. I’ve wandered its rolling hills, tasted its wines straight from the source, and watched the sun dip behind ancient stone towns — and even now, I can still see it all so vividly. There’s a certain kind of magic here that words can barely capture — maybe it’s the light, or the way time slows down and life feels beautifully simple.
If you’re planning your dream trip to Tuscany 2026, these are the towns, flavors, and quiet moments that made me fall in love with this timeless region — one step, one glass of wine, and one golden sunset at a time.
Tuscany 2026 Itinerary
Florence – Where Every Street Tells a Story
Florence is everything people say it is — and somehow even more. I still remember standing in front of the Duomo with my friends years ago, waiting in that long line under the sun. We had no idea we needed skip-the-line tickets, but it didn’t really matter then. We were young, spontaneous, and just happy to be there. When we finally made it inside, the sight of the cathedral’s dome and the details carved into every corner made every minute of waiting worth it.
Now that I’m a little older (and hopefully wiser), I’ve learned that planning ahead makes all the difference. On my recent trip back to Florence with my family, we booked a guided tour in advance — and it completely changed the experience. Our guide, Constanza (or Giulia, depending on who’s leading that day), shared stories and insights that made the city come alive in a way I’d never experienced before. From understanding the history behind the Duomo to noticing the little details I once walked past, Florence felt new again — familiar, but richer.
If you want to make the most of your time in Florence, I’d highly recommend booking your tour in advance. It saves you from the long queues and lets you focus on what truly matters — exploring the city’s beauty with a knowledgeable local guide who brings every detail to life.
Siena – The Beating Heart of Tradition
Siena has a charm that feels entirely its own. The moment you step into Piazza del Campo, it feels like you’ve stumbled upon something secret and timeless — a grand, sunlit square that still carries the echoes of the Palio horse race every summer. The medieval streets twist and turn, leading you to hidden corners where time seems to slow down.
What I love most about Siena, though, is how genuine everything feels — especially the food. It’s comforting and soulful, the kind that makes you want to linger. I still remember sitting in a small trattoria where the owner poured me a glass of local Chianti wine and insisted I try her homemade pici all’aglione — thick hand-rolled pasta with a garlicky tomato sauce that’s pure Tuscan comfort.
Chianti – Hills, Wine, and the Tuscan Dream
Driving through Chianti is one of those experiences that makes you slow down without even realizing it. The hills roll endlessly, vineyards surround you on all sides, and every curve of the road seems to reveal another postcard view. I remember stopping at a small, family-run winery where the owner handed me a glass of Chianti Classico and said, “This is what we do best.” We talked about his vineyard, his family, and how each bottle tells a bit of their story.
If you’re visiting, spend time in Greve, the lively town at the center of the region, or Castellina and Radda in Chianti, where you’ll find quiet charm and great views. Chianti is also where I had one of the best meals of my life — a perfectly cooked bistecca alla Fiorentina, paired, of course, with a local red wine. Whether you’re with friends or your partner, it’s one of those places that makes you appreciate good food, good wine, and good company all at once.
San Gimignano – Towers and Timeless Views
San Gimignano looks like something out of a storybook. Its tall stone towers rise above the hills, and the views are unreal. I climbed one just before sunset, and the light over the fields turned everything golden.
Later, I sat on the steps of the main square with gelato from Gelateria Dondoli — the best I’ve ever had — and just watched life go by. No rush, no noise, just that perfect Tuscan calm.
I’ve been there myself, and if you want to experience the best of Chianti the way I did, I highly recommend joining this tour — it’s the perfect way to taste, explore, and truly feel the heart of Tuscany.
Pisa – More Than a Leaning Tower
Of course, everyone comes to see the Leaning Tower — and it’s absolutely worth it — but Pisa surprised me in other ways. I loved walking along the Arno River at dusk, when the sky turned pink and everything slowed down. But don’t just stop in Pisa; take the time to visit nearby Lucca, like I did. It’s a charming little town surrounded by Renaissance walls, perfect for biking or just wandering its quiet streets. Together, Pisa and Lucca make the perfect day — one iconic, the other peaceful, both full of that easy Italian rhythm that stays with you long after you’ve left.
If you want to visit both Pisa and Lucca in the same day, I highly recommend booking the tour below with Fabrizio — one of the best local drivers I’ve met. He’s from the area, knows all the best photo stops and local spots, and speaks excellent English, which makes the whole trip smooth and fun.
Montepulciano – Wine and Warm Evenings
Montepulciano sits high in the hills, and every corner comes with a view that makes you stop and just breathe it in. I actually went there for business, thinking it would just be a quick visit — but Tuscany has a funny way of slowing you down. It was supposed to be a few hours, yet I found myself staying longer, caught up in its quiet beauty.
I still remember stepping into a small wine cellar carved into stone, where barrels of Vino Nobile rested in the cool dark. Later, I stood outside with a glass in hand, watching the sunset spill over the valley — simple, calm, and unforgettable.
To tell you a secret, when I booked a private driving tour to Montepulciano and Pienza, I asked my local driver where he likes to eat — the kind of spot only locals know. He smiled, made a quick call, and took us to a tiny trattoria I never would’ve found on my own. The food was everything you dream of in Tuscany: honest, flavorful, and made with heart. What started as a business trip ended up being one of my favorite memories in all of Italy.
Pienza – Small, Quiet, and Beautiful
Pienza feels like it was built for beauty. Every street has a view, and the air smells faintly of pecorino cheese from local shops. I wandered aimlessly and ended up at a lookout over the Val d’Orcia — soft hills, endless fields, and a light so gentle it almost glows.
It’s one of those places that makes you stop, take a deep breath, and just be there, completely.
If you want to experience Montepulciano and Pienza the way I did, I highly recommend booking a private driving tour. It made everything so easy — no stress about directions, parking, or timing. My driver knew every scenic backroad, the best viewpoints, and even those hidden spots that don’t show up on maps. He’s local, friendly, and speaks perfect English, which made the day feel more like exploring with a friend than taking a tour.
At My Exclusive Italy, we don’t recommend places just because they’re popular — we share them because we’ve been there. We’ve walked the vineyards, stayed in the villas, and shared long, laughter-filled meals with the locals who make these places special.
From winemakers and chefs to hosts and artisans, every connection we’ve made comes from real experiences and genuine relationships.
Because the only way to truly recommend Italy… is to know it by heart — to have tasted it, felt it, and fallen in love with it enough to share it with you.