Iconic Places to Visit in Tuscany for First-Timers

Tuscany is one of Italy’s most iconic regions, and planning your first trip can feel overwhelming. How many days do you need? Which towns are worth visiting? Where should you stay? In this guide, you’ll find the best places to visit in Tuscany for first-timers – from famous Renaissance cities to medieval villages, rolling vineyards, and postcard-perfect landscapes. If you’re visiting Tuscany for the first time, this list will help you decide what to see, what to skip, and how to plan an unforgettable trip.

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How Many Days to Spend in Tuscany

There is no simple answer to this question, but the longer you stay in Tuscany, more places you will see and the better you will know the region. If you enjoy slow travel so that you can experience the place, I would recommend somewhere between a week and two weeks. Thus, you will be able to visit the big cities and some of the villages and perhaps take a tour to the vineyards.

Of course, you can always take a city break to Florence, for example, of let’s say 3-4 days, with a day trip or two in the region.

When Is the Best Time to Visit Tuscany

Each season in Tuscany has its own unique charm, so no matter when you visit, you’re in for a treat. Summer (July and August) is hot and busy, with more tourists at the major towns and attractions.

If you prefer cooler weather and smaller crowds, consider visiting in the spring or autumn. These shoulder seasons are perfect for wandering the countryside, enjoying wine tastings, and capturing the iconic Tuscan landscapes without the hustle and bustle of peak summer.

How to Get Around Tuscany

Exploring Tuscany’s hilltowns, vineyards, and medieval villages is easiest with a car. While Florence, Pisa, and Lucca are well connected by train and bus, many of the smaller towns, like San Gimignano, Volterra, and Montepulciano, are much easier to reach if you have your own wheels. Driving also gives you the freedom to stop at scenic viewpoints, wineries, and charming villages along the way.

If you’re staying in the countryside or planning to visit multiple towns, renting a car is the most convenient option. You can compare prices and book securely through DiscoverCars for pick-ups at Florence, Pisa, or Siena, or Rome, for a fly-and-drive holidays.

For first-time drivers in Italy, remember to watch out for ZTL (limited traffic) zones in city centers and plan your parking in advance. If you prefer public transport, buses and trains can handle shorter day trips, but a car opens up the real Tuscan countryside.

We travelled around Tuscany by car and I can tell you that this is the best way to feel the charm of the countryside. It gives you both freedom and comfort. Just pay attention where you can park and where not, as we ended up with a lovely fine in Volterra.

Best Places to Visit in Tuscany for First-Timers

We spent 8 days in Tuscany for our summer holiday and absolutely loved it. While some towns were busy with tourists, we also discovered quieter gems that made the trip even more special. Based on our experience, here’s a guide to the best places to visit in Tuscany for first-time visitors.

On the Google map above I have marked in red the places, which we had visited during our 8-day stay in Tuscany. With purple are marked bigger cities and with yellow smaller villages to visit, if you are staying longer in Tuscany. See below for the suggestions.

1. Florence – The Cradle of the Renaissance

When in Tuscany, start with Florence. This Italian city is practically an open-air museum of the Italian Renaissance and it deserves more than a one-day visit. However, if you are going to Tuscany for the first time, you can’t see everything, but a glimpse of Florence will make you fall in love with it, so that you come back and explore each corner of this amazing place.

The Uffizi Gallery is the must-see place for all art lovers. Botticelli, Da Vinci, Michelangelo, Titian – are just a few of the famous Renaissance artists whose works can be admired in the oldest art gallery in the world. Pre-book your tickets to skip the long lines and explore the masterpieces at your own pace.

Another eye-catcher in Florence is without a doubt the Cathedral (Il Duomo) with the Baptistery and the Bell Tower. The dome is designed by no other than Brunelleschi and the bell tower by Giotto. It’s no surprise why the historic centre of Florence belongs to the family of UNESCO World Heritage Sites. To skip long lines and guarantee entry, you can book your tickets in advance here.

If you want to see the original David of Michelangelo, then head to the Gallery of the Academy (Galleria dell’Accademia). Take a walk on the famous Ponte Vecchio and if you want to learn more about the greatest poet of Italy, follow the Dante route and visit his house. If you are into beautiful gardens (just as we are), then you should not miss the Boboli Gardens with the Pitti Palace. Reserve your entrance tickets here for a hassle-free visit to Florence’s stunning gardens.

And then come back to Florence on another occasion. Why not even do a city trip for a couple of days?

Read more: One day in Florence – the perfect itinerary – to plan the perfect day in Florence during your Tuscan holidays.

2. Siena – A Medieval Icon

Siena is another place where time has stopped somewhere in the 14^th century. Everything in Siena revolves around Piazza del Campo and all streets lead there. The famous fan-shaped square hosts twice a year the popular horse racing event – the Palio di Siena. The square is proudly dominated by the Town Hall (Palazzo Pubblico) and its Torre del Mangia. With its 102 m it’s the second highest bell tower in Italy after the one in Cremona.

Siena has its very own amazingly beautiful cathedral (Il Duomo) of black and white marble with a stunning façade – a fine example of eclectic architecture with Gothic, Romanesque and Classical features. Secure your tickets in advance to explore this Gothic masterpiece efficiently.

For the most beautiful views of Siena and the surroundings, go up to the Medici Fortress (Fortezza Medicea). Siena’s medieval centre is also among the UNESCO’s World Heritage Sites.

3. San Gimignano – The City of Beautiful Towers

San Gimignano is an absolute must-see in Tuscany and you will notice from quite a distance why – the skyline with medieval towers is second to none. From the 72 towers that were built until the 14^th century, there are only 14 left today. Some of them were used as houses, which was quite popular in the Middle Ages.

The centre of San Gimignano is a UNESCO World Heritage Site. For one of the most amazing views in Tuscany, climb Torre Grossa. Take a walk around the city walls for more beautiful views and visit the Collegiate Church (Il Duomo) to admire the frescoes of Domenico Ghirlandaio. Book ahead of time a San Gimignano pass to see both the frescoes and the climb the tower.

Read more: The towers of San Gimignano – medieval frenzy or architectural genius – to find out why there are so many towers in this hilltop town in Tuscany.

4. Volterra – The City of Alabaster

Volterra is one of Tuscany’s hidden gems. If you are a history geek, or just curious about the past, Volterra won’t disappoint you. To learn who the Etruscan were, visit the famous Guarnacci Museum or the Etruscan tombs. To find out why Volterra is called “the city of alabaster”, visit the Ecomuseum of Alabaster.

Volterra is quiet and less touristy compared to other places in Tuscany. Take your time to walk around and enjoy its medieval charm. Do not miss the remains of the ancient Roman Theatre, as well.

Read more:  Volterra – Italian charm and Etruscan heritage – a complete city guide of this beautiful medieval city.

More Beautiful Towns and Villages in Tuscany

If you are staying longer in Tuscany (for example 2 weeks), then you can add to your itinerary Pisa (check out this post about the hidden gems in Pisa), Lucca, Arezzo or some of the smaller places: Grosseto, Pistoia, Monteriggioni, Montepulciano, Cortona. But remember Tuscany is a no-rush destination and you should enjoy it properly. On the Google Map above you can find those extra places.

Where to Stay in Tuscany

To get an idea of the country life in Tuscany, my suggestion is to stay either in an agriturismo or a fattoria (a small farm with a B&B). You should avoid the busy city centres, otherwise you will be in the middle of the tourist crowd, especially in cities like Florence or Siena.

Villa Alba – San Gimignano

We stayed in Tuscany in a lovely villa with a swimming pool just outside of the city walls of San Gimignano. It was a quiet place and in less than 10 minutes we could pop up in the historical part, thus we could explore San Gimignano as much as we wanted, both during the day and night.

I won’t exaggerate if I say that Villa Alba is one of the loveliest accommodations I have ever stayed in. The hosts were amazing and each morning we were waking up with this unforgettable smell of warm croissants. I know that I should be supposed to associate France with the smell of croissants, but for me it will be Tuscany because of our lovely hostess and her freshly baked croissants.

If you’re looking for similar accommodations with guaranteed availability, check out villas and agriturismos near San Gimignano on Booking.com – many have pools and countryside views like Villa Alba.