Best towns in Tuscany for first-time visitors
(a local guide’s picks – me!)
After a lot of thinking (or maybe not!) you’re finally planning your first trip to Italy and Tuscany is an important leg – I hope so. I know also that it can feel overwhelming — there are so many beautiful towns that it’s easy to get paralyzed.
As a local guide and foremost, in love with my region, I’ve noticed that first-time visitors often end up in the same places, missing some incredible towns that offer a more authentic and peaceful experience.
Here are my top choices for beginners, perfect for couples, families, and everybody who wants charm, culture, wine, and that classic Tuscan atmosphere… without the crowds.
1. PIENZA — the most romantic town in Tuscany
Designed during the Renaissance as the “ideal city”, it’s elegant, quiet, and filled with golden light in the afternoon. If you want a place that feels straight out of a movie set, Pienza is it.
Why it’s perfect for first-timers:
– Contfy, easy to explore in a few hours.
– Spectacular views of the Val d’Orcia area.
– Fantastic boutique hotels for couples and Agriturismi (Agri farm) for your stay.
– Great base for exploring other beautiful towns such as Montalcino & Montepulciano, among others.
What I love as a guide and a food lover:
The town invites you to eat lots of pecorino cheese, literally. You get the atmosphere of a local, little town and the views at sunset are unreal.
2. VOLTERRA — history, alabaster & zero rush
Volterra is one of the most underrated towns in Tuscany. It has Etruscan roots, medieval streets, and even a Roman theater — but without the crowds of San Gimignano.
Why it’s perfect for first-timers:
– Authentic, slower pace
– Medieval atmosphere.
– Rich history in a compact center
– Alabaster workshops available for visits and demonstration.
– Close enough to Siena and the coast
My local tip:
Visit in the late afternoon – the stone buildings glow in warm colors you can’t capture anywhere else and end your day with a local glass of wine. *Pisa wine areas
3. CORTONA — a charming hilltop “Under the Tuscan Sun”
Thanks to Frances Mayes Under the Tuscan Sun, Cortona’s popularity increased but it was still cozy and welcoming. It’s ideal for slow travelers who want great wine, amazing views, and a lively evening atmosphere.
Why it’s perfect for first-timers:
– Great restaurants and wine bars.
– Fantastic views across the valley.
– Easy base for exploring southern Tuscany.
– Lots of small luxury hotels and villas.
Guide’s take:
Cortona is best for couples who like good food, long strolls, and evenings with a glass of Chianti on a terrace.
4. BOLGHERI — for wine lovers who want something different
Most beginners head straight to Chianti – totally understandable -, but Bolgheri — on the Tuscan coast — is a dream for wine lovers. This is the homeland of Super Tuscans like Sassicaia and Ornellaia.
Why it’s perfect for first-timers:
– Excellent wineries.
– Beautiful (and famous!) cypress-lined avenue.
– Gentle seaside atmosphere.
– Gourmet restaurants everywhere.
– NO crowds.
My suggestion:
Pair a Bolgheri visit with a stop in the beach town of Castagneto Carducci, you won’t regret it!
5. MONTEFIORALLE — a tiny gem frozen in time
If you’re looking for a peaceful escape near Florence, Montefioralle is one of the smallest and loveliest hilltop villages in Tuscany. Many visitors never hear of it.
Why it’s perfect for first-timers:
– Close to Florence and easy to combine to a Chianti wine tour.
– Authentic medieval atmosphere.
– Incredible photo spots.
– Quiet but full of wine tasting opportunities.
What I love:
It’s one of the rare places that still feels untouched by mass tourism.
Which Town Should You Choose?
All of them!!
… Kidding! just remember: Tuscany is best enjoyed slowly. Pick one or two towns, stay a few nights, and let the rhythm of the countryside set the pace.
👉 Let’s plan your perfect adventure — harvest, history, and hearty meals included. Send me a message HERE and I’ll help you choose the best experience for your trip.