Known to the locals as Toscana, to the rest of the world, Tuscany epitomises the romantic, picture-perfect image of rustic Italy. Spanning much of central Italy from the Apennines to the Tyrrhenian Sea, the landscape changes from pastoral to the rocky hills of Chianti, the mountainous region of Montagnola and the flat landscapes of Pisa.
Imagine a place where rolling hills stretch toward the horizon, every village tells a story, and each glass of wine brings you closer to the land. Visiting Tuscany means stepping into a region where history, cuisine, and natural beauty blend seamlessly—designed for curious travellers seeking beautiful landscapes, inspiring culture, and a warm, personal touch. Let’s explore the top things to do in Tuscany with Designer Journeys in this blog post!
Post Contents
- Why Visit Tuscany?
- Top Things to Do in Tuscany
- 1. Explore Florence’s Compact City Centre and Renaissance Treasures
- 2. Climb Medieval Towers and See Piazza del Campo in Siena
- 3. Go Wine Tasting in Local Wineries of the Chianti Region
- 4. Wander San Gimignano’s Medieval Streets and UNESCO-Listed Sites
- 5. Marvel at Pisa’s Iconic Leaning Tower and City Walls
- 6. Glide Above Cypress Trees on a Hot Air Balloon Ride for a Bird’s-Eye View
- 7. Relax in Southern Tuscany’s Hot Springs, Surrounded by Beautiful Scenery
- 8. Join a Pasta Cooking Class or Traditional Cooking Class in a Tuscan Villa
- 9. Try Truffle Hunting in the San Miniato Hills
- 10. Savour Traditional Dishes Like Hearty Vegetable Soup and Vino Nobile di Montepulciano
- 11. Experience the Thrilling Horse Race Held During the Palio di Siena
- 12. Discover Hidden Gems in Small Towns and Picturesque Main Squares
- 13. Unwind at Elegant Beach Clubs in Western Tuscany
- 14. Hike or Bike Through Olive Groves and Narrow Streets Lined with Cypress Trees
- 15. Plan a Road Trip to Visit Places That Offer Panoramic Views and Unforgettable Memories
- 16. Live the Dolce Vita & Explore Tuscany in an Ape Tuk-Tuk
- 17. Lay Eyes on the UNESCO World Heritage Site, Val d’Orcia
- Practical Tips for your Tuscany Trip
- F.A.Qs
- Ready to Design Your Perfect Tuscany Trip?
Why Visit Tuscany?
With centuries of impactful history housed in this central region, Tuscany is world-renowned as an artistic powerhouse and the ultimate introduction to the fruits of Italy’s land. Tuscany’s effervescent charm oozes from its medieval hill towns, wine-soaked villages and swathes of rolling olive groves. You’ll be hard-pushed to find a more romantic part of Italy than Tuscany.
Art lovers rejoice. Tuscany has charmed its inhabitants since the Etruscans first arrived and indeed, the Romans left an array of exquisite monumental sculptures in their wake, but it was during the medieval and Renaissance periods that Tuscany truly shone. From the murals on Florence’s backstreets to the city’s galleries, which burst with incredible paintings and sculptures, Tuscany will impress any art buff.
Within each region of Italy, you’ll find mouthwatering cuisine you’ll savour your entire trip, and Tuscany is no different. Whilst much of its delicious produce can be found in other regions, it’s the concentration in which Tuscany’s fine wines, artisan olive oils and gourmet home-cooked dishes are delivered that fuels its status as one of Italy’s food capitals.
Top Things to Do in Tuscany
Let’s design your ideal itinerary with these handpicked, must-do experiences—each crafted for those who want insight, authenticity, and unforgettable memories.
1. Explore Florence’s Compact City Centre and Renaissance Treasures
Begin in the beautiful city of Florence, Tuscany’s capital city and a UNESCO World Heritage Site. Walk the narrow cobblestone streets of the city centre, discover world-famous art by Leonardo da Vinci and other famous artists, and enjoy the vibrant atmosphere around every corner. The compact city centre means you’re never far from a masterpiece, a charming piazza, or a cosy trattoria.
Florence is a city where you can feast on Tuscan cuisine and marvel at the astonishing works of art that fill both the city’s streets and museums.
2. Climb Medieval Towers and See Piazza del Campo in Siena
Visit Siena, one of Tuscany’s most historic towns, and climb its medieval towers for stunning views. The heart of the city is the breathtaking Piazza del Campo, a picturesque main square where the thrilling horse race held during the Palio di Siena takes place. Take time to visit Siena Cathedral, a highlight for architecture and history lovers.
Siena, Tuscany.
Not far from Siena, you’ll find the medieval hill town of San Gimignano encircled by 13th-century walls. Owing its beautifully preserved historical centre to a 13th-century law which banned the destruction of medieval buildings, visiting San Gimignano is like stepping back in time. You can explore both Siena and the city of towers, San Gimignano, with an experienced local guide on a trip like this 10-Day Rome, Ponza, Tuscany & Florence adventure.
3. Go Wine Tasting in Local Wineries of the Chianti Region
Allow yourself to be fully immersed in the enchanting landscape of the Tuscan hills. On this 9-Day Gastronomic Rome to Venice Adventure, you’ll pass through the Chianti region in Tuscany and embark on an intimate excursion to three different wineries with an expert sommelier. Thanks to its beautiful climate and rich soil, the Chianti region produces some of the world’s finest wines, known as ‘Super Tuscans’. Savouring the taste of these rich Tuscan wines, you’ll learn to distinguish the scents of flavours of each one whilst in the most fascinating settings – from medieval castles and noble villas to a boutique winery.
The enchanting landscape of the Tuscan hills.
If you want to do things a little differently, on this 10-Day Luxury & Charm of Central Italy trip, you can kick off your tour of the Chianti wine region with a hot air balloon ride over the vineyards of Tuscany, endless olive groves and ancient townships; there’s nothing quite like it!
4. Wander San Gimignano’s Medieval Streets and UNESCO-Listed Sites
San Gimignano, a hilltop town known for its medieval towers, offers a glimpse into Tuscany’s past. Explore its medieval streets, admire the stunning countryside from the city walls, and uncover hidden gems in its UNESCO-listed historic centre.
Old street in San Gimignano, Tuscany.
5. Marvel at Pisa’s Iconic Leaning Tower and City Walls
Regarded as two of the most architecturally and historically rich cities in the world, Pisa and Lucca are essential destinations for anyone seeking to immerse themselves in Tuscany’s artistic heritage. Beyond admiring the renowned Leaning Tower and the stunning Pisa Cathedral, you’ll gain insights into their compelling histories, construction processes, and their emergence as iconic symbols of Tuscany. In Lucca, you’ll wander through its historic centre, characterised by charming cobblestone streets, centuries-old churches, and bustling squares, all surrounded by beautifully preserved Renaissance walls that inspire awe and admiration.
Pisa and Lucca are essential destinations for anyone seeking to immerse themselves in Tuscany’s artistic heritage.
Of course, in Tuscany, a day trip is not a day trip without the taste of a delicious Tuscan speciality. In Lucca, you’ll end the day with a Buccellato tasting, a typical Lucchese cake. As the locals would say: “Those who come to Lucca without eating the Buccellato are like they have never been there!”
6. Glide Above Cypress Trees on a Hot Air Balloon Ride for a Bird’s-Eye View
For a truly unique experience, take a hot air balloon ride over Tuscany’s countryside. Soar above cypress trees, olive groves, and beautiful landscapes—an unforgettable way to see the region’s breathtaking landscapes and rolling hills from a new perspective.
A large hot air balloon over the center of Florence.
7. Relax in Southern Tuscany’s Hot Springs, Surrounded by Beautiful Scenery
Southern Tuscany is famous for its natural hot springs. Imagine soaking in warm, mineral-rich waters, surrounded by beautiful scenery and stunning views—a seamless blend of nature and relaxation, perfect for nature lovers and those seeking a break from city life.
The natural hot springs in Saturnia.
8. Join a Pasta Cooking Class or Traditional Cooking Class in a Tuscan Villa
Discover the secrets of Tuscan cuisine in a hands-on cooking class. Learn how to make traditional dishes like hearty vegetable soup and hand-rolled pasta, all guided by a local expert in a charming villa or farmhouse. It’s a delicious way to connect with Tuscany’s culture.
9. Try Truffle Hunting in the San Miniato Hills
If there’s one food that Tuscany is world-famous for, it’s truffles. The star of the Tuscan food scene, every species of truffle found in Tuscany ripens at a different time of year. The white truffle in Autumn and the black and brumal truffle in winter are two of the most popular. Tuscany boasts eight regions from which to truffle hunt, and the hills of San Miniato, which straddle Florence and Pisa, are one of the most prominent producers of truffles in Tuscany.
Truffle hunting in Tuscany, Italy.
10. Savour Traditional Dishes Like Hearty Vegetable Soup and Vino Nobile di Montepulciano
No journey is complete without tasting Tuscany’s most beloved foods and wines. From Vino Nobile di Montepulciano to robust soups and truffle-infused dishes, every meal is a tribute to regional tradition and creativity. Dine in historic towns, hilltop villages, or beautiful city centres.
Old red wine barrels used for ageing Vino Nobile di Montepulciano in the historic town of Montepulciano, Tuscany.
11. Experience the Thrilling Horse Race Held During the Palio di Siena
If your trip coincides with the Palio di Siena, don’t miss the thrilling horse race held in Piazza del Campo. This centuries-old tradition transforms the city into a stage for passion, rivalry, and pageantry—offering a glimpse into Tuscany’s living history.
The thrilling horse race held in Piazza del Campo.
Image source: visitsiena
12. Discover Hidden Gems in Small Towns and Picturesque Main Squares
Tuscany’s charm is often found in its small towns and hidden gems. Take a day trip to places like Montepulciano or Pienza, stroll through picturesque main squares, and chat with locals—every encounter adds depth and colour to your journey.
Tuscany, Pienza medieval village.
13. Unwind at Elegant Beach Clubs in Western Tuscany
Head to Western Tuscany for exclusive beach clubs and pristine shores. This lesser-known side of Tuscany blends luxury, beautiful scenery, and a relaxed atmosphere—ideal for families, couples, or anyone looking to recharge by the sea.
14. Hike or Bike Through Olive Groves and Narrow Streets Lined with Cypress Trees
Active travellers will love hiking or biking through Tuscany’s countryside. Discover scenic routes past olive groves, vineyards, and cypress-lined roads, then wind through narrow streets in charming medieval towns—perfect for photography and fresh-air adventures.
Biking through Tuscany countryside.
15. Plan a Road Trip to Visit Places That Offer Panoramic Views and Unforgettable Memories
Design your own road trip with a rental car, exploring Tuscany’s countryside, historic villages, and breathtaking landscapes at your own pace. With so many major destinations conveniently located within a few hours of each other, your Tuscany highlights can include city centre gems and tranquil hilltop retreats—all in one seamless journey.
16. Live the Dolce Vita & Explore Tuscany in an Ape Tuk-Tuk
Tuscan towns and medieval villages are known for their quaint winding streets and hilltop positions, however, this can make getting around them a little tricky. The Ape Tuk-Tuk was developed by local Tuscans living in small villages as a means of navigating the streets and delivering goods to and from farms. Used for over sixty years, these three-wheeled buggies have become an iconic image of Tuscany, and on a trip like this 10-Day Luxury & Charm of Central Italy adventure, you can explore the rolling Tuscan countryside and several wine tastings as part of the experience.
The Ape Tuk-Tuk was developed by local Tuscans living in small villages.
17. Lay Eyes on the UNESCO World Heritage Site, Val d’Orcia
The quintessential image of Tuscany, Val d’Orcia is a spectacular landscape dotted with ancient fortresses, quaint Tuscan villages and an abundance of vineyards that produce Brunello and other fine Tuscan wines. The cypress trees steal the show in Val d’Orcia; lined up neatly along countryside roads, swooping up and down across the landscape with the hills and ravines.
The UNESCO World Heritage Site, Val d’Orcia.
Travelling through the countryside on this 6-Day Culture and Wine in Tuscany trip, you’ll pass through characterful villages such as Pienza and the beautiful medieval hilltop city of Montalcino and finish the day at a local wine cellar where you’ll taste the world-renowned Brunello of Montalcino and a selection of typical local products.
Practical Tips for your Tuscany Trip
The Best Time to Visit Tuscany
Like many of Italy’s regions, Tuscany’s peak season is during its summer months from May to September. July and August bring soaring temperatures and crowds, making these months the busiest, most expensive and most uncomfortable time to take a Tuscany trip. Due to its mix of terrain from the cooler mountains to the intense heat of its coastline and valleys, Tuscany’s weather varies.
August is when the locals take their holidays, so as the cities empty, regions such as Tuscany fill with Italian travellers. Many of the hotels in this region consider this time the low season.
Tuscany’s peak season is during its summer months from May to September.
In the winter, from November to March, temperatures are cool, main sights close earlier and fewer activities occur in the region. However, November is also prime truffle season in Tuscany, so to make the most of this delicacy, this is the month to take a trip to Tuscany. If you choose to travel during this season, it is best to visit Tuscany with a local, as then you can ensure activities will go ahead.
The best time to visit Tuscany is the shoulder season, which falls either side of the region’s busiest months. Planning a trip to Tuscany during April and May or October and November will mean fewer crowds, comfortable temperatures and lots of activities. During these months, you may need a light jacket in the evenings, but the days will bring blue skies and sunshine.
How to Get Around Tuscany
Tuscany is a region so harmonious with its land that it demands to be explored on foot and by bicycle. But when that’s not possible, railways and country roads link this region’s greatest finds with ease.
Siena attracts visitors with its medieval towers and UNESCO status, while Pisa’s city walls and train station make it a convenient base for exploring other Italian cities and nearby towns. A fairly-sized region, much of Tuscany can be traversed in just a few hours. Trains and buses connect the major towns and cities in Tuscany, making these modes of transport the easiest way to get around. Trains are also among the most affordable ways to travel around Italy; many regions offer dedicated passes to explore the top cities and towns over several days.
However, if you plan to spend your trip exploring Tuscany’s abundance of remote villages and off-the-beaten-track towns, travelling by car is the best way. Many of the train routes don’t reach the smaller areas, which means you’ll have to rely on bus travel to reach towns such as San Gimignano. As buses are not the most reliable or convenient, travelling by car wins in these situations.
Tuscany is a region so harmonious with its land that it demands to be explored on foot and by bicycle.
Planning your Tuscany trip with a local guide means you can choose between travelling in Italy by private car with a driver or self-driving. If you decide to drive yourself, your rental vehicle will be pre-arranged and waiting for you when you arrive in Tuscany.
Tuscany has two international airports, the Galileo Galilei International Airport in Pisa and the Amerigo Vespucci Airport in Florence. Both are accessible from major European cities, but Pisa is the larger airport.
Where to Stay in Tuscany
Due to its popularity as one of the top regions in Italy, Tuscany offers a wide variety of accommodations from hotels to B&Bs and apartments for those who like to self-cater. Staying in a hotel is the most popular choice of accommodation for Florence, Siena, Pisa and other larger cities in Tuscany.
In the countryside, farmhouses converted into guesthouses are popular places to stay for those who want to combine the charm of the Tuscan countryside with the warm hospitality of a local host. Choosing to base yourself in one of the countryside towns or villages over one of Tuscany’s larger cities means having a car as transport would be very useful, as in this 6-Day Culture and Wine in Tuscany trip.
Tuscany offers a wide variety of accommodations from hotels to B&Bs and apartments.
One of the best places to base yourself in Tuscany is in the central area between Florence and Siena. Here, you won’t be far from the Chianti wine region and the San Miniato Hills, and you’ll be less than an hour’s journey from the many sights in Tuscany: Florence, Pisa, Lucca, San Gimignano, Montalcino, Montepulciano, Siena, Volterra, Arezzo, the Crete Senesi and the Val d’Orcia. Many of these areas boast an array of locally-owned villas and farmhouses that enable you to enjoy the peacefulness and beauty of the hills, coast and mountains of Tuscany.
If you’re on a shorter trip like this 9-Day Culture between Tuscany and Naples adventure, you can base yourself in a central city such as Florence and spend your days driving out to the surrounding regions. This way, you’ll be able to experience the artistic beauty of Florence whilst being a short journey from Tuscany’s major sights. If you have a little more time, such as on the 12-Day Culture and Wine in Central Italy trip, you can split your stay between a larger city like Siena and a countryside town like Lucca.
Must-Try Foods and Places to Eat and Drink in Tuscany
Tuscany is the region of a thousand flavours. Truffles and fine Chianti and Brunello wines steal the show, but the enormous pride Tuscans take in the quality of their produce shines through every dish, snack and aperitif. A gourmet destination, many people flock to Tuscany to spend the majority of their trip wining and dining like you would on this 6-Day Culture and Wine in Tuscany trip.
Every bit of produce is local, seasonal and sustainable in Tuscany. Whether you’re enjoying artisan pasta cut by hand in a family-run trattoria, a glass of Brunello di Montalcino in a world-class estate or sinking your teeth into bistecca alla fiorentina (a chargrilled T-bone steak), life is simply delicious in Tuscany.
Bistecca alla fiorentina (a chargrilled T-bone steak).
One thing you must not miss in Tuscany is the taste of truffles. One of the most traditional Tuscan products, the truffle can be enjoyed in a variety of ways, each one varying hugely in flavour. A bit like diamonds, finding truffles is an activity cherished among locals in Tuscany. You can join in finding the crème de la crème of truffles in the San Miniato Hills with an expert-gatherer and his truffle-hunting dog on this 10-Day Rome, Ponza, Tuscany & Florence trip.
Producing some of the world’s finest wines is what Tuscany does best. Chianti, Vino Nobile Montepulciano, Brunello di Montalcino and Vernaccia di San Gimignano are four wine varieties that you should taste, savour and enjoy whilst in Tuscany. Of course, like wine, Tuscan olive oil is also world-famous. Each November, olives are hand-picked from the olive groves that scatter the Tuscan hills and are sent to be pressed.
Tuscan olive oil is world-famous.
Foodies will want to indulge in Tuscan food delights such as: Panzanella, a cold bread salad with unsalted bread, red onions, tomatoes, basil, olive oil, vinegar and salt; Lardo di Colonnata, pork lard cured in local marble in Colonnata; Castagnaccio, a traditional cake made with chestnut flour common to the Apennine mountainous area of Tuscany; and Pici, a type of spaghetti from the area of Siena.
The Cost of a Trip to Tuscany
So, how much is your Tuscany tour going to cost? If this answer were simple, there wouldn’t be a whole section dedicated to it. The cost of your Tuscany trip comes down to several different variables, including:
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The length of your trip
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The season or month you travel in
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Your accommodation class
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How many places you visit or stay in
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The number of activities or tours you take part in
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Your expenditure on shopping and dining
Your travel style can also affect the cost of your Tuscany trip. Do you like to travel alone, as a family, just with your spouse or with friends? Also, do you want to travel by public transport, in a private car with a driver or by bicycle? However you like to travel and whoever you want to travel with, making sure your Tuscany trip is perfect whilst staying within your budget can cause a little bit of a headache. Luckily, with Designer Journey, it doesn’t have to be.
You can choose to design your Tuscany trip with an in-destination Local Designer who has been approved by Designer Journey to offer unique, tailor-made trips through our website. When designing your trip, the Local Designer will take into account your budget, choice of activities, class of accommodation, trip duration, and so much more. Using this information, they can create a trip that is perfect for you and every member of your party. Whether you’d like a fully-guided trip with a local there every step of the way or just the occasional guided activity, the choice is yours. With Designer Journey, you can relax in the knowledge that every detail of your Tuscany trip has been taken care of for a price that suits you.
The cost of a tailor-made Tuscany trip starts at roughly $2,700 per person for a 12-day trip. As an example, this 12-Day Culture and Wine in Central Italy includes:
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3-star hotels
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Thirteen activities and day tours
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Transport by private car and train
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A licensed English-speaking guide
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Airport transfers
This is the perfect example of a budget-friendly Tuscany trip, which could be made even cheaper by opting to stay in smaller cities and reducing the number of places you visit by staying longer in one or two of them.
If you’re looking for a luxury Tuscany trip, your Local Designer can upgrade the class of accommodation and include more guided activities. This 10-Day Luxury & Charm of Central Italy trip is the perfect example of a luxury Tuscany trip and includes:
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5-star hotels
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Twenty-six activities and day tours
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Transport by private car and train
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A licensed English-speaking guide
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Airport transfers
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Three dinners and one lunch and breakfast every day
With Designer Journey, you can design your perfect Tuscany trip by browsing our range of fully-customisable Italy trips and tailoring any one of them to your preferences with an expert Local Designer. Or better yet, select what you want out of a trip using the ‘Design your Own Trip’ function and let a Local Designer create your ideal trip.
F.A.Qs
Best time to visit Tuscany?
April to June and September to October, for beautiful scenery and mild weather.
Do I need a car?
Not in major cities (Florence, Siena, Pisa). For the countryside, hilltop towns, or wine tours, a rental car or private tour is ideal.
How many days should I spend?
Three days for Tuscany highlights, five to seven days for a crafted itinerary including both city centre sights and the countryside.
Is Tuscany good for families and seniors?
Absolutely—gentle pace, seamless support, and expert-guided experiences for all ages.
How do I visit multiple towns?
Combine regional trains for major cities with a car or private driver for small towns and the countryside.
Are cooking classes, wine tastings, and truffle hunting available everywhere?
Yes—across the region, with options for all tastes and levels of adventure.
What are must-try foods and wines?
Hearty vegetable soup, handmade pasta, truffle-infused dishes, Chianti wines, and Vino Nobile di Montepulciano.
Ready to Design Your Perfect Tuscany Trip?
Take away the stress of planning your Tuscany trip and making sure it meets your budget, whilst including everything you’d like it to. From Florence’s Renaissance treasures to the stunning countryside, every experience in Tuscany can be crafted to match your dreams. Explore hilltop towns, taste wine in sun-drenched vineyards, join cooking classes, or simply wander through picturesque villages. With warm local insight, expert support, and endless possibilities, Tuscany is yours to imagine, create, and explore—together.
With the help of one of Designer Journey’s in-destination Local Designers, you can tailor your Tuscany trip to suit the needs of everyone in your party with a wide range of locally-inspired and culturally-rich activities that few travellers have the chance to take part in.
Get inspired by our range of Italy trips or design your own trip from scratch by connecting with a Local Designer who can take care of it all.
Visit Italy in another place? Check out Designer Journeys guide for your best travel inspiration.
