Frozen in time as a memory of the Renaissance, Tuscany is one of the most beautiful and interesting places I have visited. During my degree in Art History and Classics, I became enchanted with studying Italy. From ancient Rome through the Second World War, the history of this magical country captivated me. I studied abroad in Cortona and returned four years later to complete my MA in Florence. The time I spent living in Tuscany was nothing short of incredible. The food, the wine, the art—all of my favourite things were on display at their finest.

This region is my absolute favourite to plan trips for- feel free to message me for a personalized itinerary if you’re planning on visiting Italy! Below you will find some information about my favourite places in Tuscany.

Florence

Florence, ruled by the famous Medici family- the innovators of modern banking- still feels their presence 600 years later. As the centre of this region, it’s a great hub to base yourself. The riches of Florence are displayed in its museums, where you will find all the Renaissance masters’ most celebrated paintings, as well as artifacts from its famous inhabitants (the finger of Galileo is on display at the Museo Galileo!). The Duomo towers over the city in the main square and is a tourist highlight. You can climb all 414 stairs to the top of the campanile (bell tower) for a view over the city. You can easily find the best wines from the region at any store, indulging in Chianti and Supertuscans for prices unheard of at home. Head across the Ponte Vecchio to Oltrarno—the other side of the river Arno—for a less touristy, more trendy side of Florence. Here, you’ll find some of the best wine bars and restaurants in the winding streets that make up this part of the city. Florence has a vibrance that makes you feel alive. Everyone there is enjoying themselves, whether it’s locals meeting outside in the square for a glass of wine in the evening or tourists on vacation enjoying an Aperol spritz.

Notable Food & Drink: Florentine cuisine is based on fresh ingredients and steeped in historic tradition. The most famous dish is Bistecca alla Fiorentina, a meal meant to be shared. This famous cut of steak brings people together, highlighting the social aspect of sharing a meal, which is one of the reasons I love the way Italians eat. When in Florence, head to the Mercato Centrale and don’t miss the Trapizzino, a pizza pocket filled with traditional Italian foods (it originated in Rome but it’s one of my favorite things I ate in Florence). The most famous sandwich shop in Florence, All’Antico Vinaio, is another must-visit when it comes to food. This region is famous for its black truffles, and a popular tourist activity is going on a truffle hunt. I would also highly recommend taking a cooking class in any of these cities so you can show off to your friends when you return home.

Cortona

Cortona is my favourite town in Tuscany, as this is where I did my study abroad when I was 21 years old. The months spent here were absolute bliss. Discovering Italy after wanting to visit and studying Italian for so many years felt like a dream come true. The quaint town provided us with an authentic experience where we became close friends with many locals and traveled to every corner of the country. Cortona was featured in the film Under the Tuscan Sun, which is why many people visit. The city is full of steep hills that reward you with the most beautiful views. Cortona sits at a high elevation, and many mornings you can see the sun rise above the clouds. Spending months here was easy as there is so much to explore—cute shops and restaurants, endless weekend trips, and a beautiful monastery outside the city. Our favourite nights were spent with a bottle of wine shared between friends in the town square.

Pienza

Pienza is, in my opinion, the cutest town in Tuscany. The village was rebuilt as an ideal Renaissance town by Pope Pius II and renamed for him. A stop on a day trip to Pienza provides enough time to explore the narrow streets and incredible views. Wander down Via dell’Amore, Via della Fortuna, and Via del Bacio—the streets of love, fortune, and kisses—and arrive at the end to find the most spectacular view, with the rolling hills of the Val d’Orcia and the Sanctuary of the Madonna di San Biagio, a medieval church, in the background. Enjoy an outdoor glass of wine here and catch one of the most breathtaking sunsets you’ll ever lay eyes on.

Notable Food & Drink: Pienza is the capital of Pecorino cheese and hosts a cheese festival in September each year.

San Gimignano

San Gimignano stands out for its towers, 14 of which remain today from the original 72, giving the city a distinct skyline. Many towns would have looked like this in the Middle Ages, so the fact that the towers still stand is truly unique. San Gimignano is one of the towns where we visited a lovely contemporary art gallery: Galleria Continua—a break from the dominating Renaissance art of the region. It can get very touristy in the summer months but spending the night here provides you with a chance to enjoy the town in the morning and evening without the tour busses.

Notable Food & Drink: San Gimignano is known for having the best gelato in Tuscany at Gelateria Dondoli, a claim taken very seriously in this region. In a region dominated by red wines, San Gimignano is unique for its white wine, Vernaccia di San Gimignano.

Montepulciano

Montepulciano is a wine town. Piazza Grande, the main square, is famous for being featured in the Twilight series. The thing about these small towns in Tuscany is that no matter how similar the activities might be (churches, museums, food, wine), each has its own unique look and feel, making them all absolutely worth visiting. Looking over the city walls, you’ll find yourself surrounded by rolling hills lined with cypress trees, creating one of the most picture-perfect images of Tuscany, sure to have inspired many paintings.

Notable Food & Drink: Vino Nobile di Montepulciano is one of the top reasons to visit this spot. The triangle of Siena, Montepulciano, and Montalcino produces some of the best wines in the world, attracting visitors from all over for the Vino Nobile.

Montalcino

As you continue through the countryside, you’ll arrive in Montalcino. A smaller town, this spot is famous mainly for one thing: Brunello di Montalcino. Brunello is pure Sangiovese, unlike Chianti, and is aged in oak barrels. In Montalcino, you will find a walled fortress that you can climb to enjoy spectacular views of the Val d’Orcia, definitely the inspiration for many Renaissance paintings.

Siena

Siena is another walled city—common for all towns in Tuscany in medieval times. The walls of Siena remain intact, and once within them, you feel transported back to centuries ago. The city is a UNESCO World Heritage Site, with many beautiful churches and historic buildings to explore. The main square, Piazza del Campo, is the site of horse races that occur twice a year.

Notable Food & Drink: Siena is within the Chianti region, home to the most famous Italian wines. The Chianti Classico region stretches from Florence to Siena. A Chianti is made up of at least 80% Sangiovese grapes. Pici pasta, a thick spaghetti, is also a specialty of the region, commonly served cacio e pepe style or topped with wild boar ragu.

Terme di Saturnia

The thermal baths at Saturnia are a spectacular (and free) way to spend a day. Many tourists, including myself, are surprised to find hot springs in Tuscany. This was one of the times where renting a car came in handy, as getting there via public transportation wasn’t the most direct. The cascading springs flow from a waterfall into several little pools and are a comfortable 37.5°C. Popular during Roman times, they were said to be created by Jupiter’s thunderbolt opening a portal to Hell during a battle with Saturn. For this reason, they were not visited much during the superstitious Renaissance period but have gained popularity again in recent times. We visited in the spring, before the tourist season, and had no trouble finding parking or a spot to lounge and enjoy the baths for the day.

Via Francigena

For an active experience in Tuscany, try spending a day or two on the Via Francigena, an old monastic route that runs from England to Rome. We walked about 30 km in one day between Monteriggioni and Siena and had the most lovely time. You can truly experience Tuscany outside the city when hiking between the towns on this route. Along the way, we passed many small stop markers intended for pilgrims that have lasted for centuries.

Honorable Mentions that you might want to consider for your Tuscany itinerary include Pisa, Arezzo, Lucca, and Viareggio.

I hope you have enjoyed my guide to Tuscany! Comment below if you have been to any of these spots or for any other cities you’d add to this list.