Julie Italy 8 Comments

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?

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.

About Our Experience

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.

Let’s create your perfect Tuscan experience.

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 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.

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.

Tuscany Map

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 d’Orcia
  • 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

San Gimignano Italy | Tuscany Itinerary

San Gimignano

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 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.

Piazzale Michelangelo Daytime View | Tuscany Itinerary

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 we’ll be happy to help you out.

All of these itineraries start with two days in Florence. It’s possible to spend one day in Florence, but since this small city is packed with amazing sights, we think it’s 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, Michelangelo’s 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 it’s 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.

2. Day Trip to Val d’Orcia

There is a wonderful trio of towns to visit in Val d’Orcia: 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. It’s 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. It’s 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 have a 4-course lunch in a vineyard, visit two wineries in the Chianti wine region, or take a guided tour of Val d’Orcia and visit Montepulciano, Pienza, and Montalcino.

Montepulciano Italy

Montepulciano | Tuscany Itinerary


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

View of Lucca | Tuscany Itinerary

Lucca

#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 | Tuscany Itinerary

Piazza del Campo, Siena


5 Day Tuscany Itinerary

Florence, San Gimignano, Siena & Val d’Orcia

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 Tuscany’s 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.

Duomo di Siena | Tuscany Itinerary

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 d’Orcia

Spend the day road tripping to three lovely towns in Val d’Orcia: 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, it’s 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.

Things to Do in Montalcino

Montalcino | Tuscany Itinerary

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 d’Orcia

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

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 d’Orcia

Spend the day road tripping to three lovely towns in Val d’Orcia: 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, it’s 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 Italy | Tuscany Itinerary

Pienza | Tuscany Itinerary


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.

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.

Arezzo Piazza Grande | Tuscany Itinerary

Piazza Grande in Arezzo

 

Cortona Italy

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.

Volterra Tuscany Itinerary

Volterra | Tuscany Itinerary

#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 to Orvieto.

Albornoz Fortress Orvieto | Tuscany Itinerary

Albornoz Fortress in Orvieto

 

St Patricks Well 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.

Things to Do in Assisi View

Assisi, Italy | Tuscany Itinerary

 

Assisi Sunset Umbria Italy | Tuscany Itinerary

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 d’Orcia followed by a scenic drive through the rolling hills of Val d’Orcia, or lounging at your villa (if you are staying in one) with an afternoon wine tasting in the vineyard.

Italy Travel Guide Florence


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 d’Orcia: 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 Tuscany Italy

San Gimignano | Tuscany Itinerary


What We Did: Our Tuscany Itineraries

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 d’Orcia 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 d’Orcia, check into Villa Le Prata
Day 2: Pienza and Montepulciano, sleep at Villa Le Prata
Day 3: Montalcino and San Quirico d’Orcia, 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.

Palazzo Comunale Montepulciano

Montepulciano | Tuscany Itinerary

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.

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 d’Orcia. 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 don’t 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 d’Orcia 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.

More Information for Your Trip to Tuscany

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.

SIENA: Plan your visit to Siena with our articles Best Things to Do in Siena, One Perfect Day in Siena and How to Visit the Siena Cathedral.

TUSCAN HILL TOWNS: Check out our detailed guides to Montepulciano, Pienza, Montalcino, San Quirico d’Orcia, San Gimignano, Monteriggioni, Lucca, Volterra, Arezzo, and Cortona. For a full list of things to do, read our article Best Things to Do in Tuscany.


If you have any questions about this Tuscany itinerary, let us know in the comment section below and we’ll be happy to help!

More Information for Your 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. For those with more time, check out our 14 day Italy itinerary, which covers the highlights of 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.

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.

VENICE: Learn more about Venice in our article Best Things to Do in Venice. We also have guides about How to Visit St. Mark’s Basilica, where to get the Best Views of Venice, and how to spend Two Days in Venice.

CINQUE TERRE: One of the best experiences in the Cinque Terre is to hike between all five towns. If you are traveling on a budget, get our money saving tips for the Cinque Terre.

 

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 Italy Itinerary

 

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Comments 8

  1. Avatar for Natalie
    Natalie

    Thank you for sharing! Your site is my favorite, and I always look forward to your newsletter. I’m planning a trip to Italy for late May-early June and would appreciate any advice. Our group will be 8 adults and one 14 year old who is a great traveler and loves history. I’m looking at flying into Rome and staying 3-4 nights, renting a car and staying in a central located house in the Tuscan countryside for 4-5 nights, then returning the car in Florence for a 2-3 night stay, and finally taking a train to Venice for 2-3 nights (return flight from Venice). Does this seem reasonable and do you have a suggestion for the location to stay in the Tuscan countryside? I’m a little overwhelmed with the number of choices when I look at houses.

    1. Avatar for Julie Post
      Author
      Julie

      Hello Natalie. Thanks for writing in! Your itinerary looks great!! The Val d’Orcia area is gorgeous and centrally located in Tuscany. We stayed at Villa le Prata which was very, very nice. I don’t have any other recommendations for houses to stay in in that area, but you could look at Booking.com. That’s what we use to find and book hotels when we travel. Let me know if you have any other questions. Cheers, Julie

  2. Avatar for Jasmine
    Jasmine

    Hi Julie,

    Many thanks for this detailed information! I have a question. Based on your suggestion I am spending 4 days in Florence and would like to spend 2 nights in Siene – will do day trip to San Gimignano, Assi and Orvieto from here by public transport

    Do you recommend any places to stay in Siene – specially any vineyards or farmhouses close to the city center?

    1. Avatar for Julie Post
      Author
      Julie

      You’re welcome! In our Things to Do in Siena article, we have a list of recommended hotels, including where we stayed last year. They are all located in town, near the city center, and from where we stayed (Residenza D’Epoca Palazzo Piccolomini), you can walk to the train station. Cheers, Julie

  3. Avatar for Steve Epps
    Steve Epps

    Great information. I am looking at your suggestions for 3 days in Tuscany, 2 in Florence and one day going to 3 other towns in Tuscany. Do you have a tour company you would suggest to help put this together or do you that. We will need a place to stay, transportation, etc. This will be on the front end or back end of a cruise we have planned.

    1. Avatar for Julie Post
      Author
      Julie

      No, unfortunately I do not know of any tour companies that will do this for you, but a travel agent could help you make your travel arrangements. It’s relatively easy to do on your own. You will have to make a rental car reservation and then hotel bookings for Florence and 1 to 2 places in Tuscany. A few dinner reservations is a good idea as well. We give restaurant and hotel recommendations in our city/town guides so that should make your planning easier. Cheers, Julie

  4. Avatar for Karen
    Karen

    Thank you so much for your thorough and comprehensive site. I am planning our first trip to Italy from Australia and have been searching and searching and searching the internet for information. Your site has definitely been the most helpful and I have saved all of your guides to refer back to. Cheers!

    1. Avatar for Julie Post
      Author

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