Best Things to Do in Tuscany (2026 Guide)
Timeless Wanderers: Updated May 10, 2026
Wine, Art & Hilltop Towns: What Makes Tuscany Truly Special
We’ve been fortunate to spend years exploring Tuscany, and one thing we’ve discovered is that no two visits are ever quite the same.
Some days are spent wandering through Renaissance cities filled with art and history.
On others, we’re driving quiet country roads between vineyards, stopping in medieval hill towns, or enjoying a long lunch in a family-run trattoria overlooking the countryside.
That’s what makes Tuscany so special.
It isn’t just one destination—it’s a collection of experiences that somehow fit together perfectly.
Whether you’re here for world-famous wines, historic towns, rolling countryside, beautiful beaches, or incredible food, Tuscany has a way of encouraging you to slow down and enjoy every moment.
In this guide, we’ll share the best things to do in Tuscany, along with practical travel tips, beautiful places to visit, how to get around, and ideas to help you plan a memorable journey through one of Italy’s most remarkable regions.
Table of Contents
Why Tuscany Should Be Your Next Italian Destination
After years of exploring Italy, Tuscany remains one of those places that keeps drawing us back.
It has a rare combination of everything travellers hope to find in Italy: Renaissance cities filled with art and history, medieval hill towns overlooking beautiful countryside, world-class wines, incredible food, and a slower pace of life that encourages you to stay a little longer.
What makes Tuscany special is the variety.
One day you can be walking through Florence surrounded by Renaissance masterpieces, and the next you can be driving through vineyard-covered hills, discovering a small village, or enjoying a long lunch in the countryside.
Beyond the famous cities, Tuscany is filled with places that deserve your time.
Lucca, Siena, Pienza, Montepulciano, Cortona, and countless smaller towns each offer their own character, history, and experiences.
The region is also a paradise for food and wine lovers.
From Brunello di Montalcino and Chianti wines to traditional dishes such as ribollita, pappa al pomodoro, and bistecca alla Fiorentina, Tuscany celebrates simple ingredients prepared with generations of knowledge.
Add in the beaches of the Tuscan coast, the island of Elba, beautiful walking routes, and some of Italy’s most memorable landscapes, and it’s easy to understand why Tuscany continues to be one of the country’s most loved destinations.
Whether it is your first visit or you are returning for another journey, Tuscany is best for those who take the time to slow down, look beyond the famous sights, and discover the places that make the region truly unique.
We can help you plan your dream trip to Tuscany, with a personalised itinerary designed just for you.
After more than 20 years of travelling to Tuscany—and loving it so much we decided to make it our home—we now live here and explore the region at a relaxed, local pace.
Planning a trip to Tuscany is exciting, but choosing where to go, how long to stay, and how to get around can quickly become overwhelming.
That’s where we come in.
We offer a personalised planning service that helps you decide exactly how to explore Tuscany, based on your travel style, budget, and pace.
Plus, we can help you plan scenic drives, time in hilltop towns, food and wine experiences, and those small local moments that make a trip truly special—making your Tuscany holiday easier, smoother, and full of memories you’ll treasure long after you return home.
“Let us plan your perfect trip with a custom itinerary designed just for you. Fill out the form and let’s begin.”
14 Best Things to Do in Tuscany at a Glance
Explore the heart of Renaissance, Florence, Lucca, Pisa, and Siena are the best places to do this.
- Visit charming hill top towns like Cortona Montepulciano Pienza and San Gimignano
- Wine or Olive Oil tastings in the Chianti region
- Hike in the Apennines or Mont Capanne
- Go Truffle hunting
- Join a food tour in Florence
- Ride E-bikes through the hills of Valdomesa or Chianti
- Relax in Thermal Springs in Saturnia, Bagno, Vignoni, Monte Amiata or countless other spots.
- Take a pasta cooking class, its great fun.
- Ride a VESPA through the countryside.
- Tour the vineyards and wineries such as antinori nel Chianti classico and Castello di Brolio, to taste the famous chianti Classico
- Enjoy scenic drives through rolling hills and Cypress-lined roads Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
- Hit the beach – the Argentarionis the best
- Try the local dishes bistecca alla fiorentina (Florentine steak) Ribollita (vegetable and bread soup) pappa al pomodoro (tomato and bread soup) and pappardelle al singhiale (pasta with wild boar Ragu)
BEST PLACES TO VISIT
Tuscany is truly blessed with an abundance of wonderful places to visit and things to do.
With an incredible number of beautiful towns, great beaches, lovely countryside and pristine nature, you could spend weeks here and still not see everything.
As such below is a list of the most beautiful places to visit that we think are worth visiting.
In addition, some handy tips are revealed to you, which not everyone knows.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
FLORENCE
Florence the capital of Italy Tuscany region, is one of most visited cities in the world.
Florence is a city brimming with history, culture and culinary delights.
Charming squares old churches and many of the best art exhibitions in the world are just some of the highlights that this stunning city has to offer.
An absolute must is the cathedral (you can climb the dome of the Duomoas well).
Also visit Ponte Vecchio, Accademia galleria, Uffizi Gallery, and Palazzo Vecchio.
You can walk to Piazzale Michelangelo for the best sunset view in Florence, alternatively have a drink at one of the best roof top bars.
Worth noting – If you don’t want to stand in line for hours and have limited time make sure you book tickets Online in advance
LUCCA
Lucca is our favorite town in Tuscany, even though being a bit bias, since being our home base.
You can see the main highlights in just one day, but is definitely worth a longer stay.
Also known as the “city of 99 churches” there is at least one small place of worship on every corner of the old town.
The main landmark is the city walls which is just over 4 kilometers long which you can explore on foot or by bike.
In fact the best way to see Lucca is by taking a self-guided bike tour
Make sure also to climb at least one of the towers – Torre Guinigi or Torree Delle ore for the best views in town.
Both of which charactersize the city and make Lucca a true gem in Tuscany.
*HANDY TIP*
Take a Food tour in Lucca
It’s the perfect way to explore the town and taste some of the local dishes.
PISA
One of the must see places in Tuscany is the beautiful city of Pisa, while the leaning tower of Pisa is the star attraction, the Piazza dei Miracoli includes the beautiful cathedral and baptistery.
Also built in 1372, it is probably the most famous tower in the world and attracts millions of tourists every year.
Pisa town centre has much more to offer interms of sigh seeing.
Stroll along the Arno river promenade and check out the Borgio Stretto an old shopping arcade with many restaurants, cafes and shops.
Pisa is also a university town so it has a lively atmosphere and hosts greats bars, cafes and cultural events.
Worth noting – Access to the leaning tower of Pisa is limited so try to Reserve you tickets online several days in advance.
Siena
The picturesque town known for its architcture lies 70km south of Florence
Siena’s Piazza del compo is one of Europe’s most spectator medieval squares and every year hosts the famous Palio di Siena which is held twice a year in July and August.
With it incredible Duomo the imposing Torre del Mangia a historic tower over 100 meters high, Medieval streets to explore, and wonderful restaurants, there is plenty here to keep you busy all day.
Siena is a great town to use as a home base, for exploring Tuscany.
It is centrally located and has a train and a bus station so it’s easy to get to many Tuscan Hill towns from here.
*HANDY TIP*
If you stay is Siena for 1 or 2 nights CASA CISERI we stayed here on our last visit.
It’s right in the center of town, the host was amazing, ideal for exploring Siena.
VAL d’ORCIA
This UNESCO World Heritage site is certainly one of the most stunning landscapes in Italy.
Here in Val d’Orcia you will find the Tuscany you have seen from breathtaking pictures and picturesque postcards.
Visiting pretty Medieval towns like Pienza, Montalcino, and Montepulciano are just a few things you can do in the valley.
And of course, visiting the wineries is always a popular choice.
If your planning a vacation in Tuscany, then we would recommend this region.
A great place for relaxing walks among olive groves, tall cypresses, and vineyards making this area perfect for discovering Tuscan Nature.
*HANDY TIP*
On a recent trip here we stayed at Podere Spedalone with country-style rooms and outdoor pool, it was one of our favourite stays in all of Tuscany.
SAN GIMIGNANO
Know as the medieval Manhatten for its tall towers, from a distance, it resembles a medieval skyline.
San Gimignano is one of the most accessible towns in Tuscany, it is also one of the busiest, but it is must-see.
San Gimignano has more towers than any other hill towns in Tuscany, climbing these towers for a great view over the town and Tuscan landscape is one of the best things to do in San Gimignano.
It’s a great place for shopping and dining on local foods, also has the best Gelato in Tuscany with the award wining Gelateria Dondoli.
*HANDY TIP*
If your looking for a special place to stay near San Gimignano stay at Hotel L’Antico Pozzo.
CORTONA
Cortona probably made famous by the book and film Under the Tuscan Sun located in the province of Arezzo.
Cortona is set a top a hill full of Medieval and Renaissance buildings.
Visit the Etruscan academy museum and enjoy the scenic Piazza della Repubblica.
Each of these destinations showcases the diverse beauty rich history, and cultural heritage of Tuscany, making the region an enchanting place to explore.
AREZZO
Arezzo, a captivating city in Tuscany sitting on a sloping hillside, is known for its rich history and charming medieval architecture.
With its Grand Piazzas, hilltop views, and Medieval buildings and streets.
Arezzo is one of the prettiest towns in Tuscany, but it’s the historic centre of the city that you’ll fall in love with.
Among the city highlights is the central Piazza Grande with the Vasari loggia, the Palazzo Della Fraternity Dei Laici, Arezzo Cathedral, and Corso Italia, lined with boutiques and shops selling antiques.
Arezzo is famous for its monthly antique market which is held on the first weekend of every month, Dealer antique lovers and bargain hunters gather in Piazza Grande to haggle over historical treasures.
*HANDY TIP*–
Sweet Tuscany is a lovely apartment to stay in, great location, clean and lovely decorated.
Read This Next
Where to Stay in Tuscany for Wine Lovers (2026 Guide)
VOLTERRA
Volterra a gem nestled in the heart of Tuscany, offers a unique blend of rich history, stunning landscapes, and cultural experiences.
Volterra is one of the larger towns in Tuscany, it was first inhabited by the Etruscans and later by the Romans.
Volterra is enclosed by double walls of Etruscan and medieval times.
If you like narrow streets, ancient walls, and a towering fortress, you will surely love this town.
Situated on a hill 550 meters high, which offers a stunning view over the rolling hills of Tuscany.
In addition, it is particularly known for the craftsmanship of alabaster, which you can visit many of the artisan shops in town.
*HANDY TIP*
One of the nicest and best places to stay in Volterra is Hotel La Locanda this town really comes alive in the evening.
CHARMING PIENZA
Nestled in the heart of the Val d’Orcia, Pienza is a quintessential Tuscan town known for its stunning beauty.
Surrounded by the rolling hills of Val d’ Orcia, Pienza offers some of the most picturesque views in Tuscany.
A stroll through the historic center reveals countless beautiful buildings, romantic squares, and interesting museums.
Pienza with its bend of Renaissance elegance, culinary delight, and breathtaking scenery sums up the charm and allure of Tuscany.
Whether savoring local cheeses, exploring historical landmarks, or simply enjoying the panoramic views, visitors to Pienza are sure to be enticed by its timeless beauty.
GO WINE TASTING IN THE CHIANTI REGION
The Chianti region, which sits between Florence and Siena, is synonymous with picturesque landscapes and world-renowned wines.
One of the best ways to visit the Chianti wine region is on a Tour from Florence wine tasting in Chianti offers an unforgettable experience, blending scenic beauty with culinary delight.
Chianti is home to numerous prestigious wineries, where visitors can tour historic vineyards and learn about the wine-making process on this Half Day tour from Florence Visit 2 wineries in the Chianti wine region.
Most wineries often offer guided tours, providing insights into centuries-old traditions, this Tour From Florence includes lunch at a winery plus visits to Siena, Pisa, and San Gimignano.
*HANDY TIP* You can also Tour the Chianti Wine region on a Vespa
ELBA Island
Elba is an island surrounded by the sparkling Tyrrhenian Sea.
Famed for being Napoleon’s place of exile from 1814 to 1815.
The Island is much more than sun-kissed shores, beautiful beaches, and covers for a beach getaway.
Elba’s coastline is dotted with romantic villages with colourful houses right by the sea, which are a must to visit.
Particularly worth visiting is Rio Marina, a real picture book town on the island of Elba.
A visit to the capital of the island Poroterraio is also a must.
You can get to Elba by ferry from the mainland and from Sardina.
*HANDY TIP*
For a stay on Elba, we can’t go past Bais Bianica Suites it has everything for a perfect vacation.
SATURNIA HOT SPRINGS
Saturnia Hot Springs, also known as Terma di Saturnia is a renowned thermal spa destination nestled in the heart of Tuscany in the province of Grosetto.
They attract thousands of visitors every year from all over the world.
The springs are set in a picturesque landscape of rolling hills, olive groves, and vineyards adding to the charm of the location.
The most famous feature of “Saturnia Hot Springs” is the Cacale del Mulino, a service of beautiful cascading pools formed by natural travertine rock.
The attraction has become a great photo opportunity and is certainly worth the visit.
In addition to the natural pools, there is a luxurious spa complex offering a range of wellness treatments.
*HANDY TIP*
If you’re looking to relax and unwind we recommend a visit or a stay at Hotel La Fonte Del Cerro.
A COOKING CLASS IN TUSCANY
A cooking class is one of the best things to do in Tuscany.
Classes are often held in charming farmhouses or historic kitchens, providing an authentic setting.
Tuscan dishes such as handmade pasta, Ribolita, pizza, or even gelato are taught in these classes.
Experienced chefs guide students through each step, sharing tips and stories about Tuscan food culture.
The experience usually concludes with a shared meal and local wines.
*HANDY TIPS*
Here are a few highly rated cooking classes in Tuscany.
WHERE TO BASE YOURSELF IN TUSCANY
Best Places to base yourself.
If you are planning to stay in Tuscany for anything more than 3 days, you should split your time between a few different bases, so that you can see different areas of Tuscany and minimise time spent driving or taking the train out to places of interest.
For stays less than 3 days FLORENCE is certainly your best option, since you will spend a day or two visiting the sites in Florence.
If you have more time, I recommend spending a couple of nights in Florence and then picking a location outside of Florence, either the medieval charm of SIENA or the serene beauty of the countryside.
Our favourite place to stay is LUCCA an hour from Florence and ½ hour from Pisa. This small, walled city is perfect for those seeking a quieter stay and exploring Northern Italy.
BEST TIME TO VISIT
Winter (December to February)
Our favorite time to visit Tuscany is winter as it is quieter, with few tourists and all the festive decorations.
While entrance tickets for museums and monuments are the same price all year round,
Hotels and car rentals are much cheaper than the warmer months.
Summer (June to August)
Summer brings very warm weather and a busy tourist season.
If summer is the only time you can come to Tuscany, don’t despair. While its not the ideal time to visit, it’s not as if every town, beach, or vineyard is permanently packed.
You can always find that hidden gem.
If visiting in summer, you just need to plan ahead, making reservations in advance and visiting places at the right time.
Autumn (September to November)
September has great weather, lower prices, and fewer crowds.
But don’t worry everything is still in full swing, before things die down and everyone closes up for winter.
Spring (March to May)
Spring is a perfect time to visit Tuscany with mild temperatures and fewer crowds which makes it perfect to visit to historic towns, the countryside, and the coastline.
Besides Florence, which is crowded all year round, late spring isn’t packed with tourists, so you will surely enjoy your time there.
HOW TO GET AROUND TUSCANY
Renting a car is one of the best ways to explore Tuscany.
It provides the freedom to visit remote villages, scenic countryside, and vineyards at your own pace.
The smaller towns are not easily accessible by public transport, so if you want to visit places like Volterra, Pienza, Montalcino, and the countryside of Val Orcia, the best way is by car.
Tuscany has a reliable train system connecting major cities and towns. Florence, Siena, Lucca, and Pisa are all easily connected, whereas San Gimignano and Siena are better by bus.
To check prices and book I recommend using “Discover Cars”. It’s a car rental website that includes offerings from all major rental companies as well as lots of smaller local agencies.
If you prefer an easier approach, guided tours are a convenient way to see Tuscany’s highlights.
Options include wine tours, cultural tours, and day trips to cities like Lucca, Pisa, Siena and San Gimgnano.
Book a tour of Tuscany here.
Frequently Asked Questions
1. What are the must-see highlights for first-time visitors?
Florence, Siena, Lucca, Pisa, San Gimignano, the Val d’Orcia, and the Chianti wine region are the top essentials for a first trip to Tuscany.
2. How many days do I need to experience the best things to do in Tuscany?
A 7–10 day trip lets you explore Tuscany at a relaxed pace. With 3–5 days, you can still enjoy Florence plus one or two hill towns or wine regions.
3. Is it necessary to rent a car in Tuscany?
A car isn’t needed for Florence, Pisa, Lucca, or Siena, but it’s extremely helpful for exploring hill towns, wineries, and countryside like Val d’Orcia and Chianti.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
4. What is the best time of year to enjoy Tuscany’s top experiences?
May–June and September–October offer perfect weather, open vineyards, and fewer crowds—ideal for sightseeing, wine tasting, and scenic drives.
5. Are Tuscany’s wineries beginner-friendly?
Yes. Most wineries offer guided tastings, vineyard tours, and explanations suitable for both beginners and seasoned wine lovers.
6. Can I visit multiple hill towns in one day?
Yes. Towns like San Gimignano, Volterra, Monteriggioni, Pienza, and Montepulciano are close enough to combine in one or two-day itineraries, especially with a car.
7. Do I need to book attractions in advance?
For major sites—Uffizi Gallery, Accademia, Pisa’s Leaning Tower, and popular wineries—advance reservations are strongly recommended.
8. Is Tuscany good for food lovers?
Absolutely. Tuscany is known for fresh pasta, pecorino cheese, truffles, bistecca alla Fiorentina, farmhouse dining, and delicious local wines—making it a paradise for food enthusiasts.
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Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
As long-term travellers living in Italy, we’ve found SafetyWing to be a practical option for trips around Europe, offering coverage for medical care, travel delays, and lost belongings without complicated fine print.
SafetyWing
(Best for Long-Term Travel & Affordability)
We personally use SafetyWing, and have since 2019.
It’s perfect for travelling, spending multiple weeks or a whole year abroad.
You can get a Quote here.
It’s the kind of insurance you hope you never need—but you’ll be very glad you have if something unexpected happens.
Final Thoughts
Tuscany is one of those places that feels exactly how you imagine it — and somehow even better once you arrive.
From Renaissance art in Florence to medieval streets in Siena, vineyard-covered hills in Chianti, and golden sunsets over Val d’Orcia, the region offers an experience that blends culture, history, food, and landscape effortlessly.
What makes Tuscany truly special, though, is the rhythm of life.
Mornings start slowly with coffee in a quiet piazza, afternoons stretch into long lunches, and evenings are spent watching the light change over terracotta rooftops.
Whether you’re here for iconic landmarks or small village discoveries, Tuscany rewards those who take their time.
In 2026, it remains one of Italy’s most complete destinations — perfect for first-time visitors and returning travellers alike.
Plan well, travel slowly, and leave room for the unexpected. Tuscany always delivers.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – OMIO – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.