— Tuscany is one of those places for me.
I spent time there in 2024, wandering cobblestone alleys with gelato in hand, sipping Chianti in sun-drenched vineyards, and sharing laughter with locals who welcomed me like an old friend. The food? Soulful. The wine? Elegant and effortless. The people? Warm, proud, and passionate about their land. Tuscany has a way of making everything feel slower, deeper, more meaningful.
That’s why I’m beyond excited to return this November — and this time, I’m inviting a small group to come with me. As I plan this incredible journey, I wanted to share a few of the must-visit cities we’ll explore — each one full of beauty, history, and those small, unforgettable moments that define Italian travel.
Whether you’ve been dreaming of Tuscany or it’s just now landing on your radar, these towns are calling. Let’s take a little virtual stroll through them...
Florence is pure enchantment. It’s where masterpieces live — not only in museums but in the architecture, the light, the way locals drink espresso standing at the bar.
Why I love it:
The first time I stood on the Ponte Vecchio at dusk, watching the Arno River shimmer under pastel skies, I understood why Florence has inspired artists and dreamers for centuries.
Must-See: The Uffizi Gallery – Home to Botticelli’s Birth of Venus and an unforgettable collection of Renaissance art.
Must-Try Restaurant: Trattoria Sabatino – A beloved family-run spot serving hearty, home-style Tuscan fare since 1956. It’s simple, authentic, and packed with locals — the kind of place where time slows down and every bite tells a story. *No reservation accepted*
Must-Stay Hotel: AdAstra Suites – Tucked away in the trendy Oltrarno neighborhood, this hidden gem overlooks the largest private garden in Florence. Stylish, intimate, and full of character — it’s like staying in someone’s beautiful Florentine home.
Montecatini is a spa town that feels like a step back in time. Grand hotels, palm-lined boulevards, and mineral-rich waters define its rhythm.
Why I love it:
It’s the perfect base for exploring Tuscany — well-connected and relaxing. I loved taking the historic funicular up to Montecatini Alto for dinner and sweeping views.
Must-See: Montecatini Alto – A charming hilltop village reached by cable car, perfect for a sunset aperitivo.
Must-Try Restaurant: La Pecora Nera – Located in a beautiful Art Nouveau villa, this restaurant brings elegance to traditional flavors.
Must-Stay Hotel: Hotel Ercolini and Savi – A centrally located, family-run hotel with classic charm and warm hospitality. Just steps from the main piazza and spa parks, it’s a comfortable and welcoming base for your Tuscan adventure.
Lucca is one of those places that makes you want to linger. The Renaissance walls that encircle the city are now peaceful walking and cycling paths, lined with trees and locals enjoying the day.
Why I love it:
Lucca doesn’t rush you. I spent a lazy afternoon biking the entire perimeter, stopping for espresso, pastries, and the occasional photo op in sunlit piazzas.
Must-See: The City Walls – Rent a bike and take it slow. It’s the best way to see Lucca from above and feel like a local.
Must-Try Restaurant: Buca di Sant’Antonio – Classic Luccan dishes served in a restaurant with history and heart.
Must-Stay Hotel: Hotel Ilaria – Modern comfort meets historic charm, right inside the city walls.
Yes, the Leaning Tower is iconic, but Pisa offers more if you know where to look. From lively student energy to quiet corners along the Arno River, it's worth exploring beyond the square.
Why I love it:
Walking through the Piazza dei Miracoli feels like entering a dream — the white marble buildings almost glowing in the sunlight.
Must-See: The Leaning Tower of Pisa – It’s famous for a reason. If you’re up for the climb, the view is unforgettable.
Must-Try Restaurant: Ristorante alle Bandierine – A local favorite for Tuscan classics like wild boar pasta and rich, velvety soups.
Must-Stay Hotel: Hotel Bologna – A charming, centrally located hotel with cozy rooms and a great breakfast spread.
Siena sweeps you off your feet with its red-brick beauty, steep alleyways, and grand piazzas. It feels like stepping straight into a medieval painting.
Why I love it:
The Duomo took my breath away. Black and white marble, striped columns, and artwork by Michelangelo and Donatello — it’s a must.
Must-See: Piazza del Campo – One of Europe’s most beautiful squares and home to the Palio horse race.
Must-Try Restaurant: Osteria Le Logge – Elegant yet unpretentious, this hidden gem is tucked just behind the Campo. Try the truffle pasta.
Must-Stay Hotel: Hotel Athena – Located within the city walls, this hotel offers beautiful views over the Tuscan countryside.
Known as the “Medieval Manhattan,” San Gimignano is famous for its skyline of ancient towers. It’s compact, picturesque, and incredibly photogenic.
Why I love it:
This town feels frozen in time. I love wandering the cobbled lanes and imagining the centuries of lives lived within those walls.
Must-See: Torre Grossa – The tallest tower in town, and the view from the top is absolutely worth the climb.
Must-Try Restaurant: Cum Quibus – A modern spin on traditional Tuscan food, with locally sourced ingredients and artistic flair.
Must-Stay Hotel: La Cisterna Hotel – Right on the main square, with classic rooms and sweeping views of the countryside.
Tuscany has a way of opening your heart and grounding your soul. If this post sparked something in you — a longing for simplicity, beauty, or just a really good glass of wine — I’d love for you to come along.
We’ll explore all these cities (and more!) this November on a thoughtfully curated group trip with Collette. Everything is planned — you just need to say yes.
✨ Click here to learn more and reserve your spot – Tuscany is waiting. 🍷
Affiliate Disclaimer
Some of the links on Solo, Savvy, & Stamped are affiliate links. This means that if you click on a link and make a purchase, I may earn a small commission at no extra cost to you. I only recommend products, services, and experiences that I personally use, love, or believe will add value to your travel adventures.
Your support helps keep this blog running and is greatly appreciated!