Julie Italy 4 Comments

Tuscany, with its hilltop towns, breathtaking landscapes, long list of vineyards, and famous cities such as Florence, Pisa, and Siena, is one of Italy’s most visited regions. But did you also know that you can go canyoneering, relax in a hot spring, or visit an island in Tuscany?

In this guide, we list 22 of the best things to do in Tuscany, ranging from day trips to charming medieval towns to some hidden gems you might not yet know about.

Tuscany is a joy to explore and we can’t wait to share this beautiful place with you.

What is Tuscany?

Tuscany (Toscana) is a region in central Italy. Florence is the capital of Tuscany and the largest city in the region.

Tuscany is famous for being the birthplace of the Italian Renaissance, for its wine, and for its long list of UNESCO World Heritage Sites.

Famous artists such as Michelangelo, Leonardo da Vinci, Donatello, Cimabue, Giotto, Brunelleschi, Ghiberti, and Andrea Pisano left their mark throughout Tuscany (and Italy), on the cathedrals, baptisteries, and palaces in the cities throughout Tuscany.

This one region is home to multiple wines, including Chianti, Brunello di Montalcino, Vernaccia di San Gimignano, and Vino Nobile di Montepulciano. Visiting the hilltop towns to go wine tasting is one of the best things to do in Tuscany.

And Tuscany is home to some of Italy’s most famous landmarks, including the Leaning Tower of Pisa, the Florence Cathedral, the towers of San Gimignano, and Piazza del Campo in Siena.

Tuscany Map

Map of Tuscany

Best Things to Do in Tuscany

1. Visit the Historic Center of Florence

Home to the Uffizi Gallery and Michelangelo’s David, famous piazzas and bridges, the amazing Duomo, as well as palaces, gardens, and spectacular viewpoints, Florence is not to be missed on a visit to Tuscany.

Most of Florence’s top sights are located within its small, compact city center. The historic center of Florence is listed as a UNESCO World Heritage Site.

For the best experience, plan on spending at least two days in Florence. This gives you just enough time to visit the highlights, climb a few towers for panoramic views over the city, visit a few photogenic viewpoints.

Top Experiences in Florence:

  • Visit the Florence Cathedral (the Duomo)
  • Tour the Uffizi Gallery
  • Stroll across Ponte Vecchio
  • See the statues in Piazza della Signoria
  • Watch the sunset from Piazzale Michelangelo
  • Climb the steps to the top of Giotto’s Bell Tower
  • See Michelangelo’s statue of David
  • Climb the tower at Palazzo Vecchio
  • San Lorenzo Market & Mercato Centrale
  • Visit the Boboli Gardens and/or the Bardini Gardens

Florence Italy | Best Things to Do in Tuscany

Sunset at Piazzale Michelangelo | Best Things to Do in Tuscany

 Florence Italy | Best Things to Do in Tuscany

The Florence Cathedral

Plan Your Visit: Get the full list in our article Best Things to Do in Florence. Learn how to plan your time with our One Day in Florence and Two Days in Florence itineraries.

2. Spend Some Time in Siena

Siena is one of our favorite cities in Tuscany. With its incredible Duomo, picturesque main square (Piazza del Campo), medieval streets to explore, wonderful collection of restaurants, and the views from the top of Torre del Mangia, there is plenty here to keep you busy all day.

Siena is a great town to use as your home base for exploring Tuscany. It is rather centrally located in Tuscany, and has a train station and bus station, so it is easy to get to many of the Tuscan hill towns from here. And Siena also has its own list of notable sites and great restaurants.

Top Experiences in Siena:

  • Visit the Siena Cathedral
  • Enjoy the view from Torre del Mangia
  • Spend some time in Piazza del Campo
  • Visit Santa Maria della Scala
  • Stroll through the historic heart of Siena

Siena Italy Photo | Best Things to Do in Tuscany

Siena | Best Things to Do in Tuscany

 Siena Cathedral | Best Things to Do in Tuscany

Siena Cathedral


Piazza del Campo Siena

Piazza del Campo

Plan Your Visit: Get the full list of things to do in our article Best Things to Do in Siena. Plan your time with our One Day in Siena Itinerary.

3. Road Trip through Val d’Orcia

Val d’Orcia is one of the prettiest areas in Tuscany. With its rolling hills and twisting lines of cypress trees, this is one of the most photographed landscapes in Tuscany and the inspiration for Renaissance painters.

Montalcino, Pienza, and San Quirico d’Orcia are located in Val d’Orcia and this is also where Brunello di Montalcino and Vino Nobile di Montepulciano wines are produced.

Top Experiences in Val d’Orcia:

  • Visit Montalcino, Pienza & San Quirico d’Orcia
  • Go wine tasting
  • Take a photography tour
  • Visit the famous Val d’Orcia viewpoints

Montalcino Wine Tasting Photo | Best Things to Do in Tuscany

Wine tasting in Montalcino | Best Things to Do in Tuscany

4. Go Wine Tasting in Montalcino

Perched on a hilltop, overlooking the Sangiovese vineyards and stunning landscape of Val d’Orcia, a visit to this small town is a must for wine lovers.

The to do list in Montalcino is short and sweet. Climb the fortress walls for views of the town, stroll the city streets, and taste Brunello di Montalcino wine.

Montalcino | Best Things to Do in Tuscany

Montalcino | Best Things to Do in Tuscany

5. Visit the Wine Cellars in Montepulciano

This is another hilltop town where wine tasting is the #1 thing to do.

Underground wine cellars are found throughout Montepulciano, and wine tasting in one (or more) of these cellars is a must do for wine aficionados. But you can also stroll the picturesque streets, climb a tower for a view over Montepulciano, and get a history lesson in a museum.

Top Experiences in Montepulciano:

  • Visit Piazza Grande
  • Stroll the city streets
  • Taste Vino Nobile di Montepulciano wine
  • Visit an underground wine cellar
  • Climb the Clock Tower
  • Visit Temple of San Biagio

Palazzo Comunale Montepulciano | Best Things to Do in Tuscany

Montepulciano | Best Things to Do in Tuscany

6. Explore Lovely Pienza

Like Montalcino, this small town in Val d’Orcia has a very short to do list. The best thing about Pienza is strolling its very pretty streets and sampling pecorino cheese.

PRO TRAVEL TIP: Pienza, Montepulciano, and Montalcino are all located near each other, so these three towns can be visited in one busy day.

Top Experiences in Pienza:

  • Tour Palazzo Piccolomini
  • Try Pecorino di Pienza cheese
  • Visit Piazza Pio II
  • Walk the city walls
  • Stroll the side streets
  • Visit the Pienza Cathedral and its crypt

Pienza Photo | Best Things to Do in Tuscany

Pienza | Best Things to Do in Tuscany


Where to Eat in Pienza

7. Spend a Few Hours in San Quirico d’Orcia

San Quirico d’Orcia is a lesser known town in Tuscany but it is a great place to have lunch or dinner and to stroll through another picturesque Tuscan town.

This very small town is located in Val d’Orcia, not far from Montalcino and Pienza. The list of sights is small. Stroll along Via Dante Alighieri, the main street through town, visit the Collegiate Church of San Quirico d’Orcia, and visit Horti Leonini. For a small town, San Quirico is also home to a surprisingly long list of highly rated restaurants, including a few with Michelin stars.

Two to three hours is all the time you need to spend here, and most of that time will be spent at lunch or dinner.

San Quirico Lunch

Lunch in San Quirico d’Orcia


San Quirico dOrcia | Best Things to Do in Tuscany

San Quirico d’Orcia | Best Things to Do in Tuscany

8. Take a Cooking Class

One of the best things to do in Tuscany is to take a cooking class. Cooking classes are located in many towns and villas, where you learn to make homemade pasta, pizza, or even gelato.

Here a few of the highest rated cooking classes in Tuscany:



9. Relax in a Hot Spring

Tuscany is filled with beautiful sites but this one just may be one of the most unique. Cascate del Mulino, also called the Thermal Baths of Saturnia, is a hot spring that is located in southern Tuscany.

This cascading thermal spring is open all year and is free to visit. During peak tourist season, it can be a crowded spot, so plan your visit early or late in the day for the best experience, if you will be in Tuscany from June through September.

Cascate del Mulino | Best Things to Do in Tuscany

Cascate del Mulino | shutterstock.com/travelwild

10. Go Wine Tasting in the Chianti Wine Region

Chianti is a wine region that sits to the south of Florence. This wine region, also called Monti del Chianti, includes the provinces of Florence and Siena and extends towards Arezzo, Val d’Orcia, and Pisa.

This wine region is further divided into smaller appellations, including Chianti Classico, Chianti Montalbano, Colli Senesi, and Chianti Rufina, just to name a few.

You can day trip into the Chianti wine region by visiting the towns in this area (such as Siena, Arezzo, Volterra, and San Gimignano) or join a tour that has wine tastings in the vineyards in this area.

One of the best ways to visit the Chianti wine region is on a tour.

This highly rated tour includes a visit to two wineries in the Chianti Classico region with food and wine pairings.

On this half day tour from Florence, visit two wineries in the Chianti wine region.

Have a 4 course lunch in a vineyard, with wine tastings and a spectacular at the vineyard. This looks amazing and something we would like to do on our next visit to Tuscany.

You can also go truffle hunting or tour the Chianti wine region on a Vespa.

11. Stay in a Villa

One of the best experiences in Tuscany is to stay in a villa.

Staying in a villa has perks that you don’t typically get when staying in a hilltop town (although that can be a memorable experience as well). From your room, gaze across the vineyard, have a sunset dinner surrounded by vines, and have a private wine tasting. Some villas provide gourmet dinners, private tours, and some even have a pool and/or a spa.

We spent three nights at Villa le Prata, which is a short drive from Montalcino and a great home base for exploring Val d’Orcia. At the villa, we had dinner each night, plus sunset wine tastings and tours of the vineyard.

Villa le Prata | Best Things to Do in Tuscany

Villa le Prata

12. See the Leaning Tower of Pisa

The Leaning Tower of Pisa is one of Italy’s most famous landmarks. The city of Pisa is located in western Tuscany, not far from the Cinque Terre and the Ligurian Sea.

Pisa is easy to get to using public transportation and a visit here lasts just a few hours, so it makes a great day trip option from other towns in Tuscany. It can also be combined with Lucca, mentioned next.

Leaning Tower of Pisa

Leaning Tower of Pisa | Best Things to Do in Tuscany

13. Walk the Lucca City Walls

Lucca is a small town that is located near Pisa. Walking the Renaissance-era walls, climbing the numerous towers for a view over the city, and having lunch in Piazza dell’Anfiteatro all top the list of the best things to do in Lucca.

Top Experiences in Lucca:

  • Visit the Lucca Cathedral
  • Walk or bike the city walls
  • Climb Torre Guinigi and Torre dell Ore for views over Lucca
  • Have lunch in Piazza dell’Anfiteatro

Where to Eat in Lucca | Best Things to Do in Tuscany

Lunch in Lucca | Best Things to Do in Tuscany


Lucca in September

Lucca | Best Things to Do in Tuscany

Plan Your Visit: Get the full list in our article Best Things to Do in Lucca and plan your day trip in our article How to Day Trip to Pisa and Lucca.

14. Montecatini Terme

Montecatini Terme recently made it onto the list of “Great Spa Towns of Europe” UNESCO World Heritage Site. There are eleven mineral springs in Montecatini Terme and on a visit here, you can relax in a sauna and the healing thermal waters, and have a mud bath or beauty treatment.

On a visit here, you can also ride the funicular to Montecatini Alto, a small hilltop town that overlooks Montecatini Terme.

Montecatini Terme

Montecatini Terme | shutterstock.com/Hibiscus81

15. Climb the Towers in San Gimignano

San Gimignano is one of the most accessible towns in Tuscany. It is also one of the most touristy, but it is a delight to explore.

San Gimignano has more towers than any other hill town in Tuscany. Climbing these towers for a view over the town and the Tuscan hillside is one of the best things to do in San Gimignano. It’s also a wonderful place to go shopping and dine on local foods.

Top Experiences in San Gimignano:

  • Climb to the top of Torre Grossa
  • Stroll through the historic center of San Gimignano
  • Visit the Duomo di San Gimignano
  • Torri Salvucci Maggiore
  • Go shopping

San Gimignano Italy | Best Things to Do in Tuscany

San Gimignano | Best Things to Do in Tuscany


San Gimigano Tuscany

San Gimignano | Best Things to Do in Tuscany

16. Visit Cortona

Cortona is located in the southeastern corner of Tuscany. Due to its location (it takes longer to get to Cortona from Siena and Florence than many other Tuscan towns), Cortona doesn’t get quite as many visitors as the other hill towns. But don’t be expecting a ghost town. Quite a few people travel here to see Villa Bramasole, the villa made famous by the movie Under the Tuscan Sun.

Top Experiences in Cortona:

  • Visit Piazza della Repubblica
  • Stroll along Via Nazionale
  • Explore the side streets
  • Visit the Cortona Cathedral
  • Enjoy the view from Piazza Garibaldi
  • Visit the Girifalco Fortress
  • Visit Convent Le Celle

Cortona Italy | Best Things to Do in Tuscany

Cortona | Best Things to Do in Tuscany


Cortona Shopping

Shopping in Cortona

Italy Travel Guide Rome

17. Spend Some Time in Arezzo

Arezzo is located near the southeast corner of Tuscany, not far from Cortona.

With its grand piazzas, hilltop views, and medieval buildings and streets, Arezzo is one of the prettiest towns in Tuscany. On a visit here, you can fill your time by visiting the churches and art museums, enjoying the views from the fortress, shopping for antiques, and learning about jousting.

Arezzo is famous for its monthly antique market and its historical reenactments of the Saracen Joust which is held twice a year.

Top Experiences in Arezzo:

  • Visit Piazza Grande
  • Enjoy the view from the Clock Tower
  • Visit the Church of Santa Maria della Pieve
  • Stroll along Corso Italia
  • Vasari’s House
  • Fortezza Medicea
  • Visit Arezzo’s churches and cathedrals
  • Visit the Archaeological Museum and Roman Amphitheater

Piazza Grande Arezzo Italy

Piazza Grande, Arezzo | Best Things to Do in Tuscany


Arezzo Antique Market Photo

Arezzo antique market


Corso Italia Arezzo Italy

Corso Italia

18. The Mascagni Terrace in Livorno

The Mascagni Terrace, with its black and white checkered floor and views of sea, is one of the most photogenic places to visit in Tuscany.

This terrace is enormous…8,700 square meters with a balustrade of 4,000 columns. It was built between 1927 and 1951 and named after composer Pietro Mascagni.

The Mascagni Terrace is located in Livorno, a seaside town in western Tuscany.

Terrazza Mascagni

Terrazza Mascagni | shutterstock.com/Sean Pavone

19. Visit Elba

Elba, also called Isola d’Elba, is a small Mediterranean island in Tuscany. It is part of Arcipelago Toscano National Park, a series of several Tuscan islands. Elba is the largest island in this archipelago.

Napolean was exiled to Elba in 1814. He lived on the island for ten months, escaping to France in 1815.

Elba is home to beautiful beaches, crystal clear water, and small colorful towns along its coastline. You can get to Elba by ferry from the mainland and from Sardinia.


Elba | shutterstock.com/essevu

20. Walk the Walls at Monteriggioni

Monteriggioni is a small, walled town in Tuscany, Italy. It is just 30 minutes from Siena by car and bus.

A visit here is quick, with a stroll through town and a walk on the walls topping the list of things to do.


Monteriggioni | Best Things to Do in Tuscany

21. Go Canyoneering

In northern Tuscany, rivers have worked their magic, carving out gorges and canyons in the mountainous landscape. If you are looking for adventure on your visit to Tuscany, look no farther.

With an experienced guide, you can go canyoneering and river walking through these gorges.

On this tour, you will walk, swim, climb and float in the Canyon of Cocciglia. 

On this tour in Garfagnana Valley, you will go canyoning and slide down waterfalls and natural slides.


22. Visit Volterra

Volterra is one of the larger towns in Tuscany. It was first inhabited by the Etruscans and later by the Romans. One of the best things to do in Volterra is to visit the museums, to learn about the Etruscan civilization, and to visit one of the best preserved Roman theaters in Italy.

Like the other Tuscan hill towns, strolling the medieval streets, trying local foods, shopping, and climbing a tower or two are more ways to spend your time in Volterra.

Plan on spending at least a half of a day here, because there is quite a long list of sights to see.

Top Experiences in Volterra:

  • Visit Piazza dei Priori
  • Climb the tower of Palazzo dei Priori
  • Visit the Roman Theater
  • Guarnacci Etruscan Museum
  • Visit an Alabaster shop
  • Visit Fortezza Medicea
  • Visit the Ecomuseo dell’Alabastro

Volterra Tuscany Italy Photo

Volterra | Best Things to Do in Tuscany


Roman Theater Volterra

Roman theater in Volterra


Street in Volterra

Best Things to Do in Tuscany: On a Map

How to Use This Map: Click the icons on the map to get more information about each point of interest. Click the star next to the title of the map to add this map to your Google Maps account. To view it on your phone or computer, open Google Maps, click the menu button, go to “Your Places,” click Maps, and you will see this map on your list.

How to Get Around Tuscany

The best way to get around Tuscany is by car. The smaller towns are not easily accessible by public transportation, so if you want to visit places like Volterra, Pienza, Montalcino, and the viewpoints in Val d’Orcia, the best way to do it is to rent a car for a few days.

If you plan to stay in a villa, you will also need to rent a car.

Some Tuscan towns are reachable by train. On this list are Pisa, Lucca, Florence, Siena, and Arezzo.

San Gimignano and Siena are easy to get to by bus.

How Much Time Do You Need in Tuscany?

At a minimum, plan on spending three days in Tuscany. This gives you two days in Florence plus a day for a day trip to another town or two in Tuscany. Each additional day that you can add to your trip allows you to visit more hill towns in Tuscany, go wine tasting in Chianti, relax in the hot springs, and day trip to Elba.

To do everything we listed above, you will need a minimum of ten days.

In our Tuscany Itinerary, we give suggestions on how to plan your time, whether you have 3 days, 5 days, a week, or longer.

Where to Stay in Tuscany

For a quick visit to Tuscany (3 days or less) pick one location. Florence is your best option, since you will spend a day or two visiting the sites in Florence. The next best choice is Siena, a large town that is well connected to many places in Tuscany by public transportation.

With more time, I recommend spending two to three nights in Florence and then picking a location outside of Florence, either Siena, a Tuscan villa, or a centrally located Tuscan hill town.

On our most recent trip, we spent ten days in Tuscany, dividing our time between Villa Le Prata (in Val d’Orcia), Siena, and Florence.

Tours of Tuscany

Joining a tour takes out the hassle of renting a car or figuring out your transportation options. It also allows you to visit several Tuscan towns in one day or do something unique, like truffle hunting or dining in a vineyard.



Frequently Asked Questions

How many days should I spend in Tuscany?

If you want to explore several hilltop towns, go wine tasting, road trip through the beautiful landscapes of Val d’Orcia, plan on spending at least three days in Tuscany, with another day or two for Florence. You could easily spend a week in Tuscany and never run out of things to do.

What is the best month to visit Tuscany?

If you want to see Tuscany with the lush, green landscapes that make it look like a Renaissance painting, plan your visit for the month of May. By mid-summer, the landscapes turn a golden yellow and in late summer, some of the fields are tilled.

Do you need a car in Tuscany?

Many of the larger towns, such as Siena, San Gimignano, Pisa, and Lucca, are very easy to get to using public transportation. But if you want to visit the smaller towns or spend time photographing the landscapes, you will need to rent a car, because some smaller towns are very difficult or time consuming to get to using public transportation.

More Information about Tuscany

TUSCANY ITINERARY: Learn how to plan your visit with our Tuscany Itinerary, which has sample itineraries, whether you have 3 days, 5 days, or an entire week in Tuscany.

TUSCAN HILL TOWNS: Check out our detailed guides to Siena, Montepulciano, Pienza, Montalcino, San Quirico d’Orcia, San Gimignano, Monteriggioni, Lucca, Volterra, Arezzo, and Cortona.

FLORENCE: If you are planning your first visit to Florence, don’t miss our guide to the 10 Best Things to Do in Florence and how to spend two days in Florence. We also have guides about the best rooftop bars in Florence, the best viewpoints in Florence, and how to visit the Florence Cathedral.

DAY TRIPS FROM FLORENCE: Here are 15 day trips to take from Florence, with practical information on how to plan your day.

If you have any questions about the best things to do in Tuscany, let us know in the comment section below.

More Information for Your Trip to Italy

BEST OF ITALY: In our guide to the Best Places to Visit in Italy, we list 25 beautiful destinations to consider for your next trip to Italy.

ITALY ITINERARIES: If you are just beginning to plan your Italy itinerary, take a look at our 10 Days in Italy Itinerary for five different ways to spend 10 days in Italy. We also have a detailed 10 day itinerary that includes Rome, Florence, the Cinque Terre, and Venice and a 10 day southern Italy itinerary that includes the Amalfi Coast, Matera and Puglia.

ROME: For a list of the top experiences in Rome, read our article Best Things to Do in Rome. Learn how to put these together in our 2 Day Rome Itinerary and 3 day Rome Itinerary. And don’t miss our guides to the Best Views of Rome, best Rooftop Bars in Rome, and our Rome Restaurant Guide.

LAKE GARDA: Get started with our article Best Things to Do in Lake Garda. Learn how to plan your time with our Lake Garda Itinerary. We also have information about things to do in Sirmione and Riva del Garda.

DOLOMITES: For a list of where to go and what to do, read our article Best Things to Do in the Dolomites and Best Hikes in the Dolomites. Learn how to plan your trip with our Dolomites Itinerary Travel Planner.

SAN MARINO: San Marino is a tiny country located entirely within Italy. It is gorgeous to explore and one of the most underrated places to visit in Europe.

We have TONS more information about Italy in our Italy Travel Guide, including Rome, Florence, Venice, Tuscany, the Dolomites, the Amalfi Coast, the Cinque Terre, Basilicata, and Puglia.


Tuscany Bucket List Italy


Header photo credit: shutterstock.com/Gaspar Janos

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Comments 4

  1. Avatar for Beth
    1. Avatar for Julie Post

      That’s a great question. Unfortunately, to visit a lot of the hill towns, you will have to park outside of the city center and then walk in. In many towns, this is a hilly walk so it would be very tough for you to visit the smaller towns. Even in Florence, there is a lot of walking. I know there are towns and cities in Portugal that have tuk-tuk tours but I can’t think of any in Tuscany, but it would be something to Google/research, because that could be an option for you. Cheers, Julie

  2. Avatar for Kelly

    When renting a car to be in Tuscany, where should I rent? Also I keep hearing about acquiring a driving pass. Can you explain.

    1. Avatar for Julie Post

      Hello Kelly. I haven’t heard anything about a driving pass in Tuscany and I just did a very quick Google search and nothing came up. Tim and I were just in Tuscany in September 2022 and didn’t need a pass at that time. We rented a car from Avis in Siena on our first visit to Tuscany. You can also rent a car from the city you will be in just before traveling to Tuscany. For example, if you are going Rome to Tuscany to Florence, rent the car on the day you leave Rome and return it once you get to Florence. Cheers, Julie

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