If you are planning your Tuscany itinerary, there are a lot of things to consider. How long should you spend here? Where should you stay? Should you rent a car? What towns are worth visiting?
We have visited Tuscany twice. The first time was in July 2014. We spent a week in Tuscany, spending a few days in Florence followed by five days in Siena. Tyler and Kara were just kids at the time, so we learned what it was like to tour Tuscany with kids during the busy summer months.
Our second visit was September 2022. This time it was just me and Tim. On this visit we spent 10 days in Tuscany, staying in a villa, in Siena, and in Florence.
From these two visits, we learned a lot about this region, its hill towns, and how to piece together a wonderful Tuscany itinerary.
Letโs create your perfect Tuscan experience.
In this guide, we share with you the top experiences in Tuscany and then how to put them together to create your perfect Tuscany itinerary, whether you have 3 days, 5 days, or an entire week.
How to Use This Guide
First, we give a brief overview of Tuscany and a list of the top experiences.
After this brief summary, we list multiple ways to plan a Tuscany itinerary. These itineraries range from 3 days to a week or longer. Simply pick out your favorite itinerary that fits with your time frame.
You can follow these itineraries for any time of the year. However, the best time to visit Tuscany is in the spring and fall, when the weather is pleasant and crowds are lower than the busy summer months.
Overview of Tuscany
Tuscany (Toscana) is a region in central Italy. Florence is the capital of Tuscany and the largest city in the region.
Pisa, another very well-known city in Italy, sits near the coast.
In Tuscany, hill towns sit perched high above the vineyards. These smaller towns date back to Etruscan and medieval times. Strolling the picturesque streets, wine tasting, climbing the towers for breathtaking views, and getting a history lesson at the museums tops the list of things to do in these towns.
Some of the most popular hill towns to visit are Montepulciano, Siena, San Gimignano, Montalcino, Volterra, and Arezzo, but the list keeps going.
Tuscany is home to some of Italyโs most famous landmarks, including the Leaning Tower of Pisa, the Florence Cathedral, the towers of San Gimignano, and Piazza del Campo in Siena.
You can get around Tuscany by public transportation, but some small towns are harder to reach than others. If you are dependent on public transportation, some of the best towns to visit include Siena, San Gimignano, Lucca, and Pisa. For the best experience, rent a car, which gives you more freedom to explore this area.
Location of Tuscany in Italy
Best Things to Do in Tuscany
Here is a list of the best things to do in Tuscany. For the full list, and for more information about each activity, take a look at our article, Best Things to Do in Tuscany.
- Visit the historic city center of Florence
- Climb the towers at San Gimignano
- Road trip through Val dโOrcia
- Spend some time in Siena
- See the Leaning Tower of Pisa
- Go wine tasting in the Chianti wine region
- Stay in a villa
- Visit the wine cellars in Montepulciano
- Take a cooking class
- Visit Cortona, Volterra, Arezzo, Montalcino and/or Pienza
- Visit Elba
How Many Days 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, climb the Leaning Tower of Pisa, and take a cooking class.
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 dโOrcia, 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.
The view of Florence from Piazzale Michelangelo
Tuscany Itinerary Suggestions
Below are several different Tuscany itineraries, ranging from 3 days to 10 days. Pick out the itinerary that best fits your time frame and travel style. If you need any help modifications, let us know in the comment section below and weโll be happy to help you out.
All of these itineraries start with two days in Florence. Itโs possible to spend one day in Florence, but since this small city is packed with amazing sights, we think itโs best to spend a minimum of two days here. If you have a lot of time in your itinerary, you can even add a third or fourth day to Florence.
3 Day Tuscany Itinerary
Florence & a Tuscany Day Trip
On this itinerary, spend two days in Florence followed by a day trip into Tuscany from Florence. You will stay in one place, Florence, for this itinerary. Here is a brief overview of what to do, but for the full itinerary in Florence, take a look at our 2 Days in Florence Itinerary.
- Day 1: Florence: visit the Duomo, Michelangeloโs statue of David, Mercato Centrale, Palazzo Vecchio, and one or more rooftop bars.
- Day 2: Florence: visit the Uffizi Gallery, Ponte Vecchio, Boboli and/or the Bardini Gardens, and Piazzale Michelangelo.
- Day 3: Tuscany day trip: day trip into Tuscany from Florence, choosing one of the 5 options listed next.
Day Trips from Florence
We have an article that lists 15 day trips from Florence, but here are several of the best ones to consider:
1. Day Trip to Siena
Siena is cheap and easy to get to and itโs filled with amazing places to visit, including the Duomo, the main square (Il Campo), Torre del Mangia, and cobblestoned streets to explore. Learn more about how to visit Siena in our One Day in Siena itinerary โ
One Perfect Day in Siena, Italy | A Detailed Itinerary
Detailed one day for Siena, Italy.2. Day Trip to Val dโOrcia
There is a wonderful trio of towns to visit in Val dโOrcia: Montepulciano, Pienza, and Montalcino. The best way to do this is to rent a car or take a tour, since public transportation is limited and time consuming to get to these towns.
3. Visit Pisa and Lucca
Pisa and Lucca are a breeze to link together. Itโs easy to get to both of them by train from Florence. Climb the Leaning Tower of Pisa and walk the Lucca walls. Learn how to do this in our article One Day in Pisa and Lucca.
4. Visit San Gimignano and Volterra
San Gimignano is one of the most popular hill towns to visit in Tuscany. Itโs famous for its medieval towers. You can get here by bus or train from Florence but it takes 1.5 to 2 hours one way.
If you rent a car for the day, you can also include Volterra, another great hill town to visit.
Or, visit San Gimignano and Volterra together on this highly rated tour.
5. Take a Tour of Tuscany
If you only have one day to day trip into Tuscany from Florence, the easiest way to do it is to take a tour. This takes out the hassle of figuring out public transportation or renting a car for the day.
This tour includes Siena, Monteriggioni, and San Gimignano, so you get to visit three Tuscan towns in one day. Another similar option is this tour of Siena, Montepulciano, and Cortona.
You can also Siena, Pisa, and San Gimigano with the option to add on lunch in a winery in Chianti, visit two wineries in the Chianti wine region, or take a guided tour of Val dโOrcia and visit Montepulciano, Pienza, and Montalcino.
4 Day Tuscany Itinerary
Florence + Day Trips OR Florence + Siena
With four days in Tuscany, there are two ways to plan your time.
#1 Florence + 2 Day Trips
The first option is to stay in Florence the entire time. Spend two days in Florence and spend 2 days day tripping into Tuscany from Florence. To do these day trips, you can either rent a car, visit towns that are easy to get to using public transportation (Pisa, Lucca, Siena, and San Gimignano fall into this category), or take tours both days.
Here is a sample itinerary:
Day 1: Florence
Day 2: Florence
Day 3: Day trip to Pisa and Lucca
Day 4: Day trip to Siena or a guided tour of San Gimignano and Volterra
#2 Florence + Siena
Another option is to spend two days in Florence, then travel to and spend two nights in Siena. This allows you to have dinner in Siena and stroll the city streets in the morning when it is quiet and tranquil, before the day trippers arrive.
To get to Siena from Florence, you can take a bus or train. From Siena, it’s quick and easy to travel to Monteriggioni by bus.
Here is a sample itinerary:
Day 1: Florence, sleep in Florence
Day 2: Florence, sleep in Florence
Day 3: Travel to Siena in the morning, afternoon in Siena, sleep in Siena
Day 4: Morning in Siena, afternoon in Monteriggioni, sleep in Siena
Piazza del Campo, Siena
5 Day Tuscany Itinerary
Florence, San Gimignano, Siena & Val dโOrcia
With five days in Tuscany, you start to have more options for places to visit. And with that, there becomes a lot more ways to plan your time.
After spending two days in Florence, I recommend traveling into Tuscany to stay in either a hill town or a villa.
I recommend renting a car the morning you leave Florence. This allows you to travel through Tuscany at your own pace. Some hill towns are challenging to get to using public transportation and having a car will save you a lot of time.
There are a lot of ways to plan a 5-day Tuscany itinerary. Below is a great 5-day itinerary if it is your first time in Tuscany, since it includes some of Tuscanyโs most popular and notable places.
Days 1 & 2: Florence
Follow our 2 days in Florence itinerary. Sleep in Florence both nights.
Day 3: San Gimignano
In the morning, pick up a rental car in Florence. Drive to San Gimignano and spend the day visiting San Gimignano (for things to do, read our Guide to San Gimignano).
In the late afternoon, check into your hotel. Good places to stay are San Gimignano, Siena, or a Tuscan villa. Staying in Siena gives you the advantage of getting an early start to visit the Siena Duomo. You will stay in this location for three nights.
The Siena Duomo
Day 4: Siena
Spend one day in Siena. For recommendations on how to spend your time, take a look at our One Day in Siena Itinerary.
Day 5: Val dโOrcia
Spend the day road tripping to three lovely towns in Val dโOrcia: Montepulciano, Pienza, and Montalcino.
Start in Montepulciano at 10 am. Plan on spending about 3 hours here to stroll the streets and see the sights. At 1 pm, itโs a short drive to Pienza. Have lunch here, dining on Pecorino di Pienza cheese and other local Tuscan food. End the day with wine tasting in Montalcino.
Montalcino
PRO TRAVEL TIP: Once finished in Tuscany, if you have a rental car to drop, you can return it in Florence or drive to your next destination and return the car there. Most cities in Italy are best visited using public transportation, since the railway network is efficient, cheap, and eco-friendly. But if you also have plans to visit an area that is challenging to get around using public transportation, such as the Dolomites or Puglia, then hold on to the rental car.
6 Day Tuscany Itinerary
Florence, Pisa, Lucca, San Gimignano, Siena & Val dโOrcia
This itinerary is identical to the 5 Day Tuscany Itinerary, with the addition of Pisa and Lucca.
Days 1 & 2: Florence
Follow our 2 Days in Florence itinerary.
Day 3: Pisa and Lucca Day Trip from Florence
The easiest way to visit Pisa and Lucca is to travel here by train from Florence. So, before you rent a car to visit the Tuscan hill towns, day trip out to Pisa and Lucca.
For full details on how to do this, read our article One Day in Pisa and Lucca.
Leaning Tower of Pisa
Day 4: San Gimignano
In the morning, pick up a rental car in Florence. Drive to San Gimignano and spend the day visiting San Gimignano (for things to do, read our Guide to San Gimignano).
In the late afternoon, check into your hotel. Good places to stay are San Gimignano, Siena, or a Tuscan villa. Staying in Siena gives you the advantage of getting an early start to visit the Siena Duomo. You will stay in this location for three nights.
Day 5: Siena
Spend one day in Siena. For recommendations on how to spend your time, take a look at our One Day in Siena Itinerary.
Day 6: Val dโOrcia
Spend the day road tripping to three lovely towns in Val dโOrcia: Montepulciano, Pienza, and Montalcino.
Start in Montepulciano at 10 am. Plan on spending about 3 hours here to stroll the streets and see the sights. At 1 pm, itโs a short drive to Pienza. Have lunch here, dining on Pecorino di Pienza cheese and other local Tuscan food. End the day with wine tasting in Montalcino.
Pienza
7 Day Tuscany Itinerary
Adding on to the 6-day Tuscany itinerary, you now have an additional day to visit another hill town or two in Tuscany.
Follow the 6-day Tuscany itinerary above. Here are suggestions on places to visit with your seventh day. You will now stay in Siena, San Gimignano, or the villa for an additional night, for a total of 4 nights.
PRO TRAVEL TIP: Below we list five places to visit, so you can add on two or three of them, to create an 8 or 9-day Tuscany itinerary.
Pick one of these five options to add onto the 6-day itinerary to turn it into a 7-day itinerary.
#1 Arezzo & Cortona
These two towns are located relatively close to one another so they can be visited together in one day. Arezzo and Cortona can be visited in either order.
Arezzo is a hilltop town with wide piazzas, medieval streets to explore, and a fortress that offers stunning views over the town and Tuscany. Learn about jousting and shop for antiques in the monthly market. See it in photos and plan your visit with our Guide to Arezzo โ
Cortona is a smaller town with a shorter to-do list. Stroll the medieval streets, enjoy the views over Tuscany, go wine tasting, and shop in the boutique shops. Learn more in our Guide to Cortona โ
Piazza Grande in Arezzo
Cortona
#2 Volterra
Volterra is similar to other Tuscan hill towns, with its medieval streets, boutique shops, palazzos, and piazzas, but it contains a longer list of museums and archaeological sites than you will find in places like Montepulciano and Pienza. For those with an interest in history, Volterra is one of the top Tuscan hill towns to visit. Volterra is the header photo for this guide.
There is a lot to do in Volterra, so it is best to spend a half to a full day here. For a list of things to do and how to plan your time, read our Guide to Volterra โ
Volterra
#3 Orvieto
Orvieto is located in Umbria, a region of Italy that sits just to the south of Tuscany. This town shares a lot of similarities to the Tuscan hill towns, with its hilltop location, medieval streets, and historical sights. Visit the Orvieto Cathedral, venture down a well, walk the fortress walls, and explore the ancient Etruscan sights.
If you are staying in Siena, it takes about an hour and a half to drive here. Learn how to plan your visit in our guide Things to Do in Orvieto.
Albornoz Fortress in Orvieto
St. Patrick’s Well, Orvieto
#4 Assisi
Assisi is also located in Umbria. It is famous for being the birthplace of St. Francis.
This city is a delight to visit, with its streets that look like they belong on a postcard, to the long list of churches in and around the city center. It is worth it for those with an interest in the life and history of St. Francis and those who want to explore beyond Tuscany.
If you are staying in Siena, it takes about an hour and forty-five minutes to drive to Assisi. Learn how to plan your visit with our articles Things to Do in Assisi and our One Day Walking Tour of Assisi.
Assisi, Italy
St. Francis Basilica, Assisi
#5 Leisurely Day in Tuscany
Rather than filling each and every day with a visit to a new town, adding a day of downtime allows you to relax and recharge.
You can do something low-key, like take a cooking class or relaxing in the Cascate del Mulino hot spring, having a leisurely lunch at San Quirico dโOrcia followed by a scenic drive through the rolling hills of Val dโOrcia, or lounging at your villa (if you are staying in one) with an afternoon wine tasting in the vineyard.
10 Day Tuscany Itinerary
If you have 10 days in Tuscany, here is how to put together an unforgettable 10-day Tuscany itinerary.
Day 1: Florence, sleep in Florence
Day 2: Florence, sleep in Florence
Day 3: Pisa and Lucca day trip from Florence
Day 4: San Gimignano
Day 5: Siena
Day 6: Val dโOrcia: Montepulciano, Pienza & Montalcino
Day 7: Volterra
Day 8: Leisurely day
Day 9: Arezzo and Cortona
Day 10: Assisi or Orvieto
Sleep in Florence on days 1, 2, and 3. For the rest of the itinerary, stay in Siena, San Gimignano, or a villa in Tuscany.
San Gimignano
What We Did
We have visited Tuscany twice. Here are our two itineraries, which give you more options on how to spend your time.
8 Days in Tuscany: Florence & Siena in July
Day 1: Arrive in Florence from the Amalfi Coast, afternoon in Florence
Day 2: Florence
Day 3: Florence
Day 4: Morning bus to Siena, afternoon in Siena
Day 5: Siena
Day 6: Day trip to San Gimignano from Siena
Day 7: Val dโOrcia towns (Montepulciano, Pienza and Montalcino) by rental car
Day 8: Siena
Day 9: Train from Siena to Pisa to the Cinque Terre
On this itinerary, we spent three nights in Florence and five nights in Siena.
10 Days in Tuscany: Tuscany in September
Day 1: Drive from Rome to Orvieto to Val dโOrcia, check into Villa Le Prata
Day 2: Pienza and Montepulciano, sleep at Villa Le Prata
Day 3: Montalcino and San Quirico dโOrcia, sleep at Villa Le Prata
Day 4: Monteriggioni and Siena, sleep in Siena
Day 5: Volterra, quick visit to San Gimignano, sleep in Siena
Day 6: Florence, sleep in Florence
Day 7: Florence, sleep in Florence
Day 8: Florence, sleep in Florence
Day 9: Day trip to Lucca from Florence
Day 10: Visit Arezzo and Cortona, sleep in Assisi
On this itinerary, we spent three nights in Villa Le Prata, two nights in Siena, and four nights in Florence.
Montepulciano
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.
Where to Stay in Florence: Best Locations & Hotels
Best places to stay in Florence, organized by location and budget.Frequently Asked Questions
When is the best time to visit Tuscany?
The best time to visit Tuscany is in the spring and fall. In May, the Tuscan hillside is lush and green and this is the best time visit Tuscany if you want to photograph Val dโOrcia. In June, visitation starts to pick up and peaks in July and August, which are the busiest, hottest months to visit Tuscany. In September, crowds begin to lessen but rain chances increase. October is a nice time to visit Tuscany, if you donโt mind the possibility of rain.
What are the most beautiful places to visit in Tuscany?
With its rolling hills, lines of cypress trees, and picture-perfect hill towns, Val dโOrcia is one of the prettiest places to visit in Tuscany. For breathtaking views of the countryside, climb the towers at San Gimignano, Montepulciano, and Volterra.
Do you need to rent a car to visit 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.
If you have any questions about this Tuscany itinerary, let us know in the comment section below and weโll be happy to help!
More Information for Your Trip to Italy
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, Sicily, and Puglia.
Tuscany Bucket List: 22 Best Things to Do in Tuscany
Tuscany, with its hilltop towns, breathtaking landscapes, long list of vineyards, and famous cities such as Florence, Pisa, and Siena, is one of Italyโs 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 […]
25 Best Places to Visit in Italy | The Ultimate Italy Bucket List
Are you planning a trip to Italy? If so, be prepared to fall in love with an extraordinary country. The food, the wine, the history, the art and architecture, the quaint, hillside towns in Tuscany, and the picturesque Dolomites…there is something here for everyone. The list of places to visit in Italy is long. So […]
Top 10 Things To Do on Your First Visit To Florence
Florence is one of Italyโs most popular cities to visit, especially for first timers. Not only is Florence the art capital of the world, it is a gorgeous city filled with world class art museums, towers to climb, great places to go shopping, and lots of beautiful viewpoints. Here is a list of the 10 […]
San Gimignano: Best Things to Do & Photo Tour
San Gimignano is famous for its hilltop setting and medieval towers. In fact, one of the best things to do on a visit to San Gimignano is to climb one or more of these towers for a breathtaking view of Tuscany. Itโs also a wonderful place to go shopping and dine on local foods. San […]
One Perfect Day in Florence: Must-See Sights & Sunset Views
Planning a trip to Italy and only have enough time for one day in Florence? With a well-planned day, you can visit Florenceโs top sights, including the Duomo, Michelangeloโs David, the amazing Uffizi Gallery, and Ponte Vecchio. Watch the sunset, stroll through Florenceโs scenic streets, and enjoy views of the Florence Cathedral from a rooftop […]
Best Rooftop Bars in Florence with a View of the Duomo
Visiting a rooftop bar or two (or three!) is one of the best things to do in Florence. If you want drinks with a view of the Duomo, you have quite a few rooftop bars in Florence to choose from. In this guide, we cover the top picks and practical information so you can choose […]
How to Visit the Florence Cathedral (Duomo di Firenze) in 2025
The Florence Cathedral, also called the Duomo di Firenze and Cattedrale di Santa Maria del Fiore, is one of the most recognizable cathedrals in the world. A visit to this cathedral is more than just walking through the cathedral and seeing the dome. You can also climb Giottoโs bell tower, walk the stairs to the […]
Top 10 Things to Do in Siena, Italy
With its incredible Duomo, picturesque main square (Piazza del Campo), medieval streets to explore, and views from the top of Torre del Mangia, there is plenty here to keep you busy all day. In this guide, we list 10 essential things to do in Siena, a good starting point for your first visit to Siena. […]
Volterra, Italy: Best Things to Do, Map & HELPFUL Tips
Volterra is a hilltop town that is located in Tuscany, Italy. Itโs one of the larger hill towns to visit in Tuscany and can keep you busy all day, with its list of museums, archeological sites, restaurants, shops, and stunning views over Tuscany. In this guide, we cover the best things to do in Volterra […]
Lucca, Italy: Best Things to Do, Photos & Helpful Tips
Lucca is a walled city that sits in western Tuscany, not far from Pisa, the Cinque Terre, and the Ligurian Sea. Walking the Renaissance-era walls, climbing the numerous towers for a view over the city, and having lunch in Piazza dellโAnfiteatro all top the list of the best things to do in Lucca. Since it […]
Top 10 Things to Do in Montepulciano, Italy
Perched on a hilltop, overlooking the rolling hills of Tuscany, sits Montepulciano. This medieval town, with its underground wine cellars, medieval churches, and scenic streets, is a delight to explore. In this guide, we list the best things to do in Montepulciano, where to go wine tasting with a view of Val dโOrcia, and how […]
Best Way to Spend 1 to 2 Days in Bologna: A Detailed Itinerary
Bologna, famous for its medieval towers, historic churches, endless porticos, and incredible culinary scene, is an absolute delight to explore. 1 to 2 days in Bologna is just enough time to get to know this underrated city. Bologna is often overlooked by many first timers (and even second or third timers) on a visit to […]
10 Days in Italy Itinerary: 5 Amazing Ideas for Your Trip to Italy
Italy is a country that is on many travelersโ wish list. And why not? Italy has it all: fabulous cuisine, gorgeous cities, towering mountains and beautiful beaches, and ancient historical sites. Throw in some gelato and wine and you have the perfect ingredients for a memorable 10-day holiday in Europe. If you have 10 days […]
Hiking the Cinque Terre: What You Need to Know
The Cinque Terre, a UNESCO World Heritage Site, is a group of five towns perched on the dramatic coastline of Italy, just north of Pisa. The towns are easily recognizable, with their pastel buildings stacked on top of one another, overlooking the harbors below. Each town offers something a little bit different than the others, […]
Comments 34