Planning a trip to Tuscany? This guide covers everything you need to build the perfect itinerary, whether you have 3 days, 5 days, or a full week.
How long should you spend here? Where should you stay? Should you rent a car? What towns are worth visiting? These are all questions that may be running through your mind as you plan your itinerary.
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.
Tuscany Itinerary At a Glance
3 DAYS | Florence + 1 day trip
4 DAYS | Florence + 2 day trips or Florence + Siena
5 DAYS | Florence, San Gimignano, Siena & Val d’Orcia
6 DAYS | Florence, Pisa, Lucca, San Gimignano, Siena & Val d’Orcia
7 DAYS | Florence, Pisa, Lucca, San Gimignano, Siena, Val d’Orcia & more hill towns
10 DAYS | The complete Tuscan experience
April 2026 Update: Added a new section on the best time to visit, with weather data and graphs for Florence. Expanded the itineraries, added links to our new Italy content, and verified all links.
Our Tuscany Itineraries
We have visited Tuscany twice. Here is how we planned our 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. We did this itinerary with kids, and for them the highlights were Siena (they liked playing soccer in Piazza del Campo), climbing the towers in San Gimignano, and climbing the dome of the Duomo in Florence.
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.

San Gimignano
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 is packed with incredible experiences, from climbing the towers of San Gimignano to wine tasting in Val d’Orcia. For the full breakdown of top experiences and tips for each, see our Best Things to Do in Tuscany guide →
Best Things to Do in Tuscany from Hill Towns to Hidden Gems
Visit Tuscany’s top cities and hill towns, relax in a hot spring, explore underground wine cellars, go truffle hunting, and so much more.
Location of Tuscany in Italy
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.
| Trip Length | Best For | What You’ll Experience |
| 3 Days | Quick visit, first taste of Tuscany | Florence + 1 nearby town (Pisa or Siena) |
| 5 Days | Balanced trip | Florence, Siena, San Gimignano, Val d’Orcia |
| 7 Days | First-time visit, slower pace | Florence, hill towns, countryside, wine tasting, scenic drives |
How to Get Around Tuscany
The best way to get around Tuscany depends on your itinerary, but for most trips, renting a car is the best option.
- Car (best for 5–7 days): Ideal for exploring the countryside, Val d’Orcia, and smaller hill towns. Gives you the most flexibility.
- Train (good for cities): Easy and efficient for traveling between Florence, Pisa, and Siena, but limited for rural areas.
- Tours (no driving): A good option if you prefer not to drive—many day trips run from Florence to Siena, San Gimignano, and wine regions.
PRO TIP: If you are following our 7-day Tuscany itinerary, we recommend renting a car for at least part of your trip to fully experience the countryside.

The view of Florence from Piazzale Michelangelo
3-Day Tuscany Itinerary (Quick Highlights)
Florence & a Tuscany Day Trip
With 3 days in Tuscany, focus on Florence and one or two nearby destinations. This itinerary gives you a taste of Tuscany’s cities, scenery, and culture, but moves at a faster pace.
Day 1: Florence
Day 2: Florence
Day 3: Tuscany day trip
Days 1 & 2: Florence
Florence is the capital of Tuscany and one of the most art-rich cities in the world. Two days here gives you enough time to visit the highlights without feeling rushed.
On your first day, visit the Duomo, Michelangelo’s David at the Accademia Gallery, and the Mercato Centrale. In the evening, head to one of Florence’s rooftop bars for a drink with a view over the city.
On your second day, visit the Uffizi Gallery, cross the Ponte Vecchio, and spend some time in the Boboli or Bardini Gardens. End the day at Piazzale Michelangelo for sunset views over the city.
For a complete breakdown of how to spend your time, including ticket booking tips and where to eat, see our 2 Days in Florence Itinerary.
Day 3: Day Trip from Florence
On your third day, rent a car or hop on a train and head out to explore the Tuscan countryside. Below are five of the best day trip options, but for the full list see our 15 Day Trips from Florence guide.
#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, San Gimignano, and Pisa, so you get to visit three Tuscan towns in one day.
You can also visit Siena, Pisa, and San Gimigano with the option to add on lunch in a winery in Chianti or take a guided tour of Val d’Orcia and visit Montepulciano, Pienza, and Montalcino.

Montepulciano
4-Day Tuscany Itinerary
Florence + Day Trips OR Florence + Siena
With four days in Tuscany, there are two good ways to plan your time depending on your travel style.
#1 Florence + 2 Day Trips
BEST FOR: Best if you prefer staying in one place and exploring by day trip.
Spend two days in Florence followed by two days of day tripping into Tuscany. Pisa and Lucca are easy to reach by train, while Siena and San Gimignano are accessible by bus. If you want to visit smaller hill towns like Volterra or Montepulciano, rent a car for one of the days.
Here is the 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

Lucca
#2 Florence + Siena
BEST FOR: Best if you want to experience Tuscany beyond Florence and don’t mind changing hotels.
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 the 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 d’Orcia
Five days is where Tuscany really opens up. After two days in Florence, rent a car and head into the hill towns and countryside for the rest of your trip.
There are many ways to plan a 5-day Tuscany itinerary. Below is our recommendation for your first time in Tuscany, which includes some of the region’s most popular and notable places.
Day 1: Florence
Day 2: Florence
Day 3: San Gimignano
Day 4: Siena
Day 5: Val d’Orcia
Days 1 & 2: Florence
Follow our 2 days in Florence itinerary for a complete guide to the city. Sleep in Florence both nights.
Day 3: San Gimignano
Pick up your rental car in Florence and drive to San Gimignano, about 90 minutes south. Spend the day exploring the medieval towers, strolling the hilltop streets, and sampling the local gelato. San Gimignano’s white gelato has won international awards and is worth seeking out. For a full list of things to do, see our guide Things to Do in 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 a full day in Siena. The highlights are the Duomo, Piazza del Campo, and Torre del Mangia, but Siena rewards slow wandering. The backstreets away from the main square are some of the most atmospheric in Tuscany. See our One Day in Siena Itinerary for the full guide.
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.

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 d’Orcia
Already read the 5-day itinerary? This adds one day, Pisa and Lucca, before the hill towns portion begins
Six days gives you everything in the 5-day itinerary plus a day for Pisa and Lucca, which are two of Tuscany’s most rewarding cities and easy to combine in a single day by train.
Day 1: Florence
Day 2: Florence
Day 3: Pisa & Lucca
Day 4: San Gimignano
Day 5: Siena
Day 6: Val d’Orcia
Days 1 & 2: Florence
Follow our 2 Days in Florence itinerary for a complete guide to the city. Sleep in Florence both nights.
Day 3: Pisa and Lucca Day Trip from Florence
The easiest way to visit Pisa and Lucca is by taking a train from Florence. So, before you rent a car to visit the Tuscan hill towns, day trip out to Pisa and Lucca.
In Pisa, climb the Leaning Tower and explore the Campo dei Miracoli. Then take the short train ride to Lucca and spend the afternoon walking the city walls, ducking into the churches, and exploring the charming historic center. See our One Day in Pisa and Lucca guide for the full itinerary.

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.
Spend your final day road tripping through Val d’Orcia. Start in Montepulciano in the morning, stop in Pienza for lunch and a taste of the local Pecorino cheese, then end the afternoon with wine tasting in Montalcino.

Pienza
7-Day Tuscany Itinerary
Seven days is the sweet spot for first-time visitors to Tuscany. You get everything in the 6-day itinerary plus a full extra day to explore another corner of the region.
Day 1: Florence
Day 2: Florence
Day 3: Pisa & Lucca
Day 4: San Gimignano
Day 5: Siena
Day 6: Val d’Orcia
Day 7: Choose your own adventure (see options below)
Days 1 & 2: Florence
Follow our 2 Days in Florence Itinerary for a complete guide to the city. Sleep in Florence both nights.
Day 3: Pisa & Lucca
Day trip to Pisa and Lucca by train before picking up your rental car. See our One Day in Pisa and Lucca guide for the full itinerary.
Day 4: San Gimignano
Pick up your rental car in Florence and drive to San Gimignano. Spend the day exploring the medieval towers and hilltop streets. Check into your accommodation in the late afternoon — stay here for the next four nights. See our guide to San Gimignano for things to do.
Day 5: Siena
Spend a full day in Siena exploring the Duomo, Piazza del Campo, and Torre del Mangia. See our One Day in Siena Itinerary for the full guide.

Montepulciano
Day 6: Val d’Orcia
Road trip through Val d’Orcia, stopping in Montepulciano in the morning, Pienza for lunch, and Montalcino for afternoon wine tasting.
Day 7: Add One More Destination
Your seventh day is where you can tailor the itinerary to your interests. Pick one of the following options:
#1 Arezzo & Cortona
BEST FOR: Those looking to venture off the beaten path into two charming medieval towns with far fewer crowds than San Gimignano or Siena.
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.
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.

Piazza Grande in Arezzo

Cortona
See our guides to Arezzo and Cortona for things to do and how to plan your visit.
Best Things to Do in Arezzo, Tuscany (+ Map, Tips & Itinerary)
Pinterest Facebook Flipboard After two trips through Tuscany, we’ve visited a lot of hill towns, including Siena, Cortona, Montepulciano, Pienza, and a handful of smaller villages tucked into the countryside. Arezzo was one of the last ones we visited, and arriving on a Sunday in early October, we weren’t sure what to expect. What we […]
Cortona, Italy: Things to Do in This Underrated Hill Town
There’s a moment when you round a corner on one of Cortona’s side streets and the whole Val di Chiana valley opens up below you, and you think: how is this town not more famous? Tim and I had that moment during what was supposed to be a quick afternoon stopover between Arezzo and Assisi. […]
#2 Volterra
BEST FOR: Travelers who prefer a slower pace, with great museums, alabaster workshops to browse, and streets that feel genuinely off the tourist trail.
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 history buffs, Volterra is one of the top Tuscan hill towns to visit.
The Etruscan history runs deep, the alabaster workshops are worth exploring, and the views over the surrounding countryside are stunning. See our Guide to Volterra for things to do →

Volterra
#3 Orvieto
BEST FOR: Travelers curious to cross the border into Umbria and experience one of central Italy’s most dramatically situated towns without adding a separate trip.
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
BEST FOR: History and religion enthusiasts who want to visit the birthplace of St. Francis and experience the spiritual heart of Umbria.
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
BEST FOR: Those who prefer a slower pace, with time to take a cooking class, linger over a wine tasting, or spend a lazy afternoon by the villa pool.
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.
10-Day Tuscany Itinerary
The Complete Tuscan Experience
Ten days gives you enough time to cover all of Tuscany’s highlights without feeling rushed. Follow the 7-day itinerary above and add three more days to explore the towns and experiences you couldn’t fit in earlier.
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
For a deeper look at what to do in each of these destinations, see the Day 7 options in the 7-day itinerary above: all five options are covered there in detail.
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
When is the Best Time to Visit Tuscany?
Tuscany is a year-round destination, but the best times to visit are spring (April to June) and fall (September to October). The weather is pleasant, the countryside is at its most beautiful, and the crowds are more manageable than in summer.
Spring brings mild temperatures, wildflowers across the Val d’Orcia, and the first of the outdoor festivals. Late April and May are particularly lovely.
Summer (July and August) is the busiest and hottest time to visit. The hill towns get crowded and accommodation prices peak. That said, if a villa with a pool is part of your plan, summer delivers. Sunflower season runs from late June into July and is worth timing your trip around if you can.
Fall is arguably the best time to visit. September and October bring harvest season, wine festivals, and the soft golden light that Tuscany is famous for. Crowds thin out noticeably after mid-September.
Winter (November to March) is quiet and cold, with shorter days and some restaurants and shops closing in smaller towns. However, if you want Florence without the crowds, winter is your best window.
Below are weather graphs for Florence showing average temperatures and precipitation.
Where is the Best Place 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 city’s sights. The next best choice is Siena, a large town well connected to many parts of 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.
Here is our detailed where to stay guide for Florence, with recommended hotels, apartments, B&B’s, and hostels organized by location →
Where to Stay in Florence: Best Locations & Hotels
Best places to stay in Florence, organized by location and budget.Frequently Asked Questions
Is 3 days enough in Tuscany?
Three days is enough for a taste of Tuscany but not the full experience. With three days you can cover Florence plus one day trip into the countryside, which is enough to get a feel for the region but not enough to explore the hill towns at a relaxed pace. If three days is all you have, make the most of it with our 3-day Tuscany itinerary above. If you can stretch to five or seven days, you’ll leave feeling like you actually saw Tuscany rather than just passed through it.
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.
How do I avoid the ZTL zones in Tuscany?
ZTL (Zona a Traffico Limitato) zones are restricted traffic areas in the historic centers of most Italian cities and towns. Driving into one without a permit will result in a fine that typically arrives weeks after you get home via your rental car company. The simplest rule is to never drive into a historic town center. Park at the designated lots outside the walls and walk in. In Siena, San Gimignano, and Montepulciano these are easy to find and inexpensive. If your accommodation is inside a ZTL zone, contact them before you arrive, as hotels can usually register your license plate with the local authority to grant you temporary access. And never rely solely on GPS to route you around ZTL zones because most navigation apps are not reliably updated with current restrictions.
Plan Your Trip to Tuscany & Italy
If you’re planning a trip to Tuscany, these guides will help you build out your itinerary and make the most of your time in Italy:
- For an overview of destinations across the country (we have over 100 guides, from the Dolomites to the Amalfi Coast to Sicily), read our Italy Travel Guide, with tips on where to go, how to get around, and how to plan your trip.
- Want more ideas for what to see and do? See our Best Things to Do in Tuscany for a deeper dive into the top experiences across the region.
- Planning to stay in Florence? Don’t miss our guide to Florence Day Trips, with easy excursions to Siena, Pisa, San Gimignano, and more.
- Extending your trip? Follow our 14-Day Italy Itinerary to combine Tuscany with Rome, Venice, and beyond.
If you have any questions about this Tuscany itinerary, let us know in the comment section below and we’ll be happy to help! We read and answer every one.
More Information for Your Trip to Italy
Here are more of our guides about places to visit in Italy, including Rome, Florence, Venice, Tuscany, and beyond.



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