Dreamy Tuscany itinerary ideas for a perfect Italian escape
All you need to know to plan a perfect Tuscany itinerary: best places in Tuscany, where to base yourself in Tuscany, practical tips for a perfect trip
Tuscany is one of those places in Italy that seem to have a special power.
It envelopes visitors in all-around beauty, satisfies their taste buds with gratifying food and tickles their minds with centuries-old art and architecture.
I have a special connection with Tuscany, a personal one, and I am a victim of the charm of this incredible area.
Tuscany is where half of my family is from, the place that still affects the musical rhythm of my auntie’s accent, and the place I spent most of my childhood summers in.
I love it so much, I still go to Tuscany every summer and, often, more than once a year: I simply cannot get enough of it and, after you experience it, I am sure it will be the same for you!
I recommend a trip to Tuscany to everyone and, in this guide, I will try and share all you need to know to plan a perfect Tuscany itinerary, no matter your party or time available.
Heading to Tuscany with children? Check out our guide to Tuscany with kids instead!
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Table of Contents
How to plan a trip to Tuscany
The main thing you need to decide when planning a trip to Tuscany is wether you want to drive (or have a budget for car service).
Tuscany is best discovered by car: having a vehicle is the only way to reach the most scenic country restaurants, the most beautiful vineyard, the most jaw-droppingly beautiful viewpoint and even most of the hilltop towns.
To give you an idea of its location and distances between its most famous sites, this is how long it takes by car between some of its main towns:
- Florence to Lucca: 1h15 minutes
- Florence to Pisa: 1h35 mins
- Florence to Siena: 1h10 mins
- Siena to Livorno: 2h
- How to get to Tuscany
Good to know! You can rent cars from several places in Tuscany but the most convenient tend to be Florence Airport and Pisa airport. When renting, I like to use DiscoverCars to see my options: I like that you can easily compare prices and also add special criteria such as car seat for kids.
If you don’t have a car, you can also explore parts of Tuscany but you will be more limited unless you have a rather generous budget that allows for bus tours or car service.
But have no fear! in this guide, I share itinerary ideas for both Tuscany with a car and without!
Where to base yourself in Tuscany
The best place to base yourself in Tuscany depends on transport options.
Based on my experience, the best place to base yourself in Tuscany if you don’t have a car is Florence.
Florence is the capital of Tuscany, it is wonderful and very well served by trains, buses and tours that allow you to easily explore the rest of the region.
It is also a town with many opportunities for food and classes, which means you won’t be stranded with nothing to do simply because of lack of transport (this will very much be the case if you stay in the countryside with no access to a vehicle).
The best places to use as a base in Tuscany if you do have a car are:
Siena and San Gimignano
Two famous and stunning UNESCO towns, Siena and San Gimignano are among the prettiest small towns in Tuscany and are in a stellar location to explore Tuscany.
I recommend you stay in an agriturismo or villa outside yet close to the town centres, in the countryside, so you can enjoy the best of Tuscany country living and pop into the towns for sightseeing after the crowds of ay tripper have gone.
Montepulciano and Pienza
If you are coming to Tuscany for the quintessential Tuscan experience, the one made of hilltop villages, cypress trees and amazing wineries, the best base in Tuscany are the towns of Montepulciano and Pienza.
Like Siena and San Gimignano, these towns are wonderful in themselves and are perfectly located to explore Tuscany’s rolling hills.
This location is exceptionally good if you are coming to Tuscany lured in by photos of golden hills and cypress trees as this is where you find them!
This is also the area where you can taste Plenty local Rosso, Brunello, Vino Nobile and Morellino wines and famous pecorino cheese (from Pienza)
My favorite 3 days in Tuscany itinerary by car (excluding Florence)
If you only 3 days in Tuscany I recommend you follow this itinerary, which you can tackle from any of the best accommodation areas above
Day 1: head to Siena, spend the day leisurely strolling around the town so you can see Piazza del Campo and Siena’s Duomo.
Make sure you have a meal at Taverna San Giuseppe to taste local pics (pasta) and browse the local shops.
In the afternoon, head to San Gimignano and see this incredibly beautiful medieval town in the afternoon, when crowds start to subside.
Day 2: Explore the beautiful hilltop town of Montepulciano and treat yourself to lunch in scenic Podere Il Casale.
The take the scenic drive to Pienza and end the day with aperitivo and cheese taking in the breathtaking view from the city’s walls.
Day 3: Explore the lovely towns of Montalcino (famous for wine) and learn to cook in delightful Locanda Demetra. The relax and rewards yourself soaking in the relaxing and scenic thermal pools of Bagno Vignoni
Have more time? The you can use this 4 Days in Tuscany itinerary
With 4 days in Tuscany, I recommend the following itinerary.
Day 1: head to Siena, spend the day leisurely strolling around the town so you can see Piazza del Campo and Siena’s Duomo.
Make sure you have a meal at Taverna San Giuseppe to taste local pics (pasta) and browse the local shops.
In the afternoon, head to San Gimignano and see this incredibly beautiful medieval town in the afternoon, when crowds start to subside.
Day 2: Explore the beautiful hilltop town of Montepulciano and treat yourself to lunch in scenic Podere Il Casale.
The take the scenic drive to Pienza and end the day with aperitivo and cheese taking in the breathtaking view from the city’s walls.
Day 3: Explore the lovely towns of Montalcino (famous for wine) and learn to cook in delightful Locanda Demetra. The relax and rewards yourself soaking in the relaxing and scenic thermal pools of Bagno Vignoni
Day 4: spend the day in Chianti and explore the stunning wineries of this area. Treat yourself to a visit and a meal to Castello Antinori, have lunch in Verrazzano Castle, visit La Volpaia and see the picture towns of Greve and Montefioralle.
Have even longer? Itinerary for 5 days or more in Tuscany
Day 1: head to Siena, spend the day leisurely strolling around the town so you can see Piazza del Campo and Siena’s Duomo.
Day 2: Explore the beautiful hilltop town of Montepulciano and treat yourself to lunch in scenic Podere Il Casale.
The take the scenic drive to Pienza and end the day with aperitivo and cheese taking in the breathtaking view from the city’s walls.
Day 3: Explore the lovely towns of Montalcino (famous for wine) and learn to cook in delightful Locanda Demetra. The relax and rewards yourself soaking in the relaxing and scenic thermal pools of Bagno Vignoni
Day 4: spend the day in Chianti and explore the stunning wineries of this area. Treat yourself to a visit and a meal to Castello Antinori, have lunch in Verrazzano Castle, visit La Volpaia and see the picture towns of Greve and Montefioralle.
Day 5: Get on the road for a road trip to lovely Lucca, still surrounded by its stunning medieval walls, then make your way back down to your accommodation via delightful Monteriggioni to see two of the most beautiful small towns in Tuscany in a day!
3 day Tuscany itinerary without a car (excluding Florence)
As I mentioned above, visiting Tuscany without a car is tricky but it can be done, especially if you are open to taking organised day trips or car service.
in this case, my recommended itinerary is:
Day 1: Get the train to explore Lucca, stunning walled town with a perfectly preserved city center. Work up and appetite by clicking on the walls, indulge in a meal in town, then head to Pisa to see the famous leaning tower later in te afternoon, when the worst of the crowds are gone
Day 2: get a bus to Siena and explore the town at slow pace, in your own time.
You can read here >>> our guide to one day in Siena to make the most of your visit. If you are open to bus tours, this one is gentle to the budget and also includes a stop in a Chianti winery for lunch.
Day 3: I recommend you spend this day immersing yourself in a real tuscan experience by booking the farm to table experience by Tenuta Chiudendone. Tenuta chiudendone is a family home that opens its doors to guests who can experience one day in the county as if they lived there.
Isabella and Francesco, the owners, show you their vines, they delightful olive groves, they have you pick vegetables and cook lunch with them and of course sit with you for a meal.
After this, you can also lounge poolside at their salt water pool!
This is a perfect Tuscan day and the bets way to experience the Tuscany countryside without a car.
You can get in touch with them here
How to get to Tuscany
You can to Tuscany by plane, train, and car.
Tuscany is served by 2 main airports: Florence and Pisa, catering for national and international travelers.
The airports are both well located to visit the rest of Tuscany and both cities offer car rental options, bus and train connections with the rest of the country.
While not technically in Tuscany, the airport of Bologna is also a good option if you are thinking of reaching this area by plane.
Please be advised that since these airports are smaller and tourism- dependent, the availability of flights drastically diminishes in low season: make sure you check in advance when certain flights are available and on which days of the week.
With the fast trains, you can reach Florence from Rome in less than 2 hours. this is an excellent option both if you want to avoid driving and if you want to get a car once in Florence, limiting travel time from Rome.
Good to know! You can rent cars from several places in Florence but the most convenient tends to be Florence Airport as it means you can avoid inner city driving and restricted access areas. When renting, I like to use DiscoverCars to see my options: I like that you can easily compare prices and also add special criteria such as car seat for kids.
You can also read Tuscany by car from anywhere in Italy. Tuscany has excellent roads and the big motorways connect it with Rome in a fast and efficient manner.
I hope you enjoyed this guide to planning your trip to Tuscany and it helped to answer your questions about planning your best Tuscany itinerary.
Safe travels!
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