Tuscany – even the name makes us sigh. It is its landscapes that first seem to attract people to the region. Many eyes have widened with wanderlust at photos of cypress dotted hillsides, where rolling vineyards fade into burning sunsets. But beyond this earthly masterpiece, there are many great things to do in Tuscany and some incredible places to go.
Tuscany brings together everything that we love about Italy. There’s the aforementioned landscape of course. But even this is worth mentioning again as mere changes in light can create dramatic views.
Then there are the towns that hug its hilltops. Thick stone walls, fortresses and towers have evolved over centuries – they no longer defend their towns but are among the very reasons people visit them.
And obviously, there is history in Tuscany – Roman, Phoenician, Renaissance and more shaping the region and its people, culture and food. And let us not forget the food – and for that matter, the wine – Tuscany excels at both.
Things to do in Tuscany – city, coast and countryside
This guide to what to do in Tuscany will provide you with plenty of inspiration for planning your trip to this popular region of northern Italy. It will highlight its most striking cities and towns; take in where to go in Tuscany’s countryside plus Tuscany beaches you won’t want to miss. Plus we have added all of the cities and towns, attractions, vineyards, restaurants, hotels and more that are mentioned here to a Google map at the end of this feature, which you can add to your phone to take our recommendations with you.
Get a taste of Chianti with our favourite tour in Tuscany
On a tour of the region, I visited some its most popular destinations and went on a very fun tour – more details below, but this video below gives you a snapshot of the most delightful way to tour Tuscany’s famed wine region, Chianti.However, I also explored extensively and if you’re looking to put together your own Tuscany itinerary over seven days. You will find plenty of ideas for a week-long trip in this guide including some unusual but Italian-cool activities that shouldn’t be missed.
Days 1-2: Historic, art and cultural things to do in Florence
It’s only right to start Tuscany’s highlights with Florence. Italy’s first capital city will satisfy anyone passionately seeking culture, history and art and you could easily invest a day or two of your Tuscany itinerary in Florence.
Start your explorations by taking in the city’s expansive art collections at the Uffizi Galleries and the Bargello and Accademia, which house some of the world’s finest art treasures including Michelangelo’s David, and Botticelli’s Birth of Venus.
The city of the cultured, wealthy (and at times, villainous) Medici family, Florence flaunts its treasures, with all manner of statues in squares like Piazza della Signoria.
On a small group tour, a guide unveiled how a history of merchants, bankers, philosophers and artists – from Dante to Bruneschelli to Machiavelli – all left their mark on the city.
Then there are Florence’s famous buildings, of which the cathedral and baptistery are perhaps the best known. The red, white and green marble on the cathedral point to faith, hope and charity, and match the colours also found in Italy’s flag.
From the outside the cathedral is, without doubt, the most impressive of Florence’s landmarks – perhaps of all of Tuscany’s points of interest. However it doesn’t quite maintain the wow-factor from the inside.
The Santa Croce, or church of the Holy Cross, is very much worth a visit though. It exterior is similar to the cathedral in its white and coloured marble architecture, and inside it is full of some of the city’s most famous bones including the burial places of Michelangelo and Galileo.
Then there’s the Ponte Vecchio, another of the great Tuscany points of interest. It is the oldest bridge in the city after the others were destroyed on Adolf Hitler’s orders, to scupper the Allied troops’ advance in the Second World War. The bridge wears its age very well – it dates back to 1345 – and still has shops – now mostly selling gold jewellery – along its full length.
For the best views in the city, stay or have lunch, at the Grand Hotel Baglioni, or alternatively head up the hill to Piazza Michelangelo for a dramatic panorama. But be aware, it’s one of the most popular things to do in Florence and an area that can become pretty busy, especially later in the day.
You can’t visit Tuscany – the home of one of Italy’s best-known wine regions – without sampling some tasty reds, as we did on a tour of Chianti
Day 3: City of horses and history – trot around Siena
Another of Tuscany’s great cities, Siena is 80 kilometres south of Florence and is a city that wears its mediaeval history and religious heritage with pride. It also maintains one of the greatest traditions in the world. Each year 30,000 people gather in the round of Il Campo – its main piazza to race the Palio di Siena.
One of the biggest horse races in the world, the Palio di Siena, has been running since the 12th century and has created something of an equine city and is one of the major.
Evidence of this can be found in the iron hitching rings found along the city’s streets, as well as the Palio Stables.
Siena is also an important centre for Italy’s Catholic religion. It was home to Saint Caterina one of Italy’s two patron saints. There are two landmarks that should be visited to learn more about her – the Basilica Cateriniana di San Domenico, where perhaps gorily, her face and a finger are on display.
Then there is the Sanctuary of Santa Caterina, which houses two chapels and is also the site of Saint Caterina’s former home.
Meanwhile, Siena’s cathedral stands out as one of the best places to visit in Tuscany.
Unlike Florence’s cathedral, it’s not only beautiful on the outside with statues surrounding a gold inlaid mural. But the interior is a must see and wandering around its main building and library was one of my favourite things to do in Siena. Dark green and white striped marble adorns the inside (and admittedly looks like black and white stripes, hence the cathedral’s nickname as the Beetlejuice Church). Then, at the far end, you’ll find a staggering altar with highlights of gold and blue surrounding paintings.
Its painted library and floors depicting stories from the Bible, also beg to be seen making Siena cathedral one of my favourite points of interest in Tuscany.
Day 4: Great gelato in a towering town – what to see in San Gimignano
It is feasible to take a day trip from Florence to Siena and San Gimignano. But you wouldn’t want to rush these lovely Tuscan towns – especially not when you’ve seen gorgeous San Gimignano for yourself. A hillside town with history along every one of its cobblestone streets, it became a firm favourite for me.
Once upon a time, San Gimignano, just 48 kilometres (about 50 minutes drive) from Siena, had 72 towers peaking into the blue Tuscan sky and making the most of its uninterrupted views of green hills. They were built by wealthy families to show their economic power, but today just 13 of these towers remain after a change in architectural styles during the 13th century.
But the town, set at 334m above sea level, towers above its neighbours for many other reasons. Not only is there the view – worthy of the visit to San Gimignano alone, but it has numerous museums, including one all about wine.
San Gimignano also has plenty of coffee shops selling delicious cakes making its main square Piazza della Cisterna, in particular, a great place to while away an afternoon.
But be sure you don’t miss out on one of San Gimignano’s major culinary attractions – it is home to world championship gelato shop, Gelateria Dondolini. The gelateria has its own herd of cows producing organic milk, which it uses to create gelato with tongue-tingling flavours. Some of the most eclectic include white chocolate, pumpkin seed oil and cookies, white wine, and my favourite – pink grapefruit and sparkling wine, which had just enough tanginess to bring a level of fizz to the gelato.
San Gimignano has plenty of historic corners to explore so it’s worth spending a whole day there. And for those who miss the towers, you can get a sense of how the town looked in medieval times at the San Gimignano 1300 Museum. It has a huge model of the original town.
Day 5: A fine vintage – one of the coolest things to do in Tuscany
You can’t visit Tuscany – the home of one of Italy’s best-known wine regions – without sampling some tasty reds.
The Chianti region is known the world over for its vintage wines, but less so its vintage cars. But this didn’t stop us taking the most entertaining wine tour in Tuscany through the Chianti hills. It was a tour that turned out to be one of the most fun things to do in Tuscany.
Hopping into vintage Fiat 500s we spent the best part of a day whizzing around the Chianti countryside.
By today’s standards, the vintage 500s aren’t light and lithe enough to travel very far, or very fast – with a top speed of around 50 kilometres per hour. But what they lacked in speed and motoring pizazz, they more than made up for in style and fun. And our tour was a journey into Tuscany’s past, exploring endless vines to the towns crowning its hills.
Take Castellina in Chianti, for example, where we ambled the medieval street of Via Delle Volte, which forms an underground tunnel around the town, and was used to protect it from invaders. Then we visited its 14th-century castle, which offers great views of the nearby countryside.
Whether you spend one week, five days or just three days in Tuscany, be sure to put Lucca high on your Tuscany itinerary – it is one of the most authentic towns you will find in the region
Next, we unearthed the legend of the black rooster – the logo and trademark of the premium wine from the region, Chianti Classico. It dates back to the 13th century when it was drawn on the banners of the Chianti League, the military and administrative institution. But it is also linked to the ancient conflict between the republics of Florence and Siena. Tired of constant battles to define territories in Chianti, they agreed to settle the dispute with a contest, where a knight would leave each city in the morning at the crowing of a cock. The Florentine knight would head towards Siena, and Sienese’s towards Florence, and where the two met, they would seal the border.
The Florentines entrusted their wake up call to a black rooster, which they’d kept hungry the night before. The Sienese chose a white rooster, which they gave a hearty evening meal. The hungry Florentine rooster woke his knight earlier and he was able to annex a larger portion of Chianti for Florence.
Leaving Castellina in Chianti full on history, we headed to vineyard, Poggio Amorelli for lunch, and feasted on antipasti of Italian hams and meats and home-made pasta, served with wines from their vineyard – a 2013 Vermentino, a 2009 Brunello di Montalcino, and of course their Chianti Classico.
Next up, we made our way to the town of Monteriggioni. We wound our way up the hillside, the little Fiats showing steely determination to make it to the top. Another medieval town, here we heard more interesting historic tales from our guides.
Before leaving, I popped into a delicatessen and gathered enough meats, cheeses and, of course, Chianti, to weigh down our little Fiat. But the car didn’t struggle – we drove downhill all the way.
You’ll find many wine tours in Tuscany and Italy beyond, but shooting between towns and vineyards in a Fiat 500 proved to be the best fun you can have in a tiny Italian car and one of the coolest things to do in Tuscany.
Day 6: Walk on the wall side with these things to do in Lucca
Be sure to put Lucca high on your Tuscany itinerary, whether you are there for one week, five days or just three days in Tuscany. It is one of the most authentic towns you will find in the region.
The town of Lucca was something of a revelation to me. I’d never heard of it before and when I was told we were going to walk its walls I had an entirely different idea of what that meant to Lucca’s wonderful reality.
The walls are more than 20 feet deep and have been transformed into an extraordinary park-like landscape, making it one of the most popular things to do in Lucca.
Each side of Lucca’s walls has a different species of tree lining it, bringing a change in scenery at every corner and there are broad paths for walkers and cyclists to enjoy views of the old town within and modern Lucca outside the walls.
The wall walk, or you can join the hoards hiring a bike from just €3 an hour to cycle it, also provides excellent elevated views of landmarks such as the town’s striped cathedral and homes with window boxes overflowing with flowers.
Viareggio is more than a seaside escape, with style and character far beyond Europe’s other coastal resorts
But Lucca isn’t just about peace and relaxation. Head into the old town and you will find boutiques and delicatessens to excite any fashionista or epicurean. I really enjoyed wandering the shops and pausing for gelato in my afternoon in the city
Days 7-8: Relax in stylish Viareggio one of the finest Tuscany beaches
Most travel guides to Tuscany focus on its cities and countryside, perhaps even on the Chianti wine region. But there are also Tuscany beaches worthy of attention, so add Viareggio to your travel itinerary. In fact, though this was set to be a guide to how to spend seven days in Tuscany we’d recommend taking time to relax in Viareggio so stay for a day, two or even a little more. With a long stretch of golden sand, luxury hotels facing onto the coast, and fresh seafood on the menus of its restaurants, Viareggio is a great place for a few days recovery after a Tuscany tour, and if you still feel like exploring, Viareggio is also close enough for a day trip to Pisa – just 23 kilometres away.
A short 28 kilometres away from Lucca, modern Viareggio came into being after a fire destroyed many of the wooden buildings along its promenade in 1917. As a result, many of its buildings have the Art Nouveau, or Liberty style of architecture, prevalent at the time.
Viareggio became Italy’s most popular resort in the 1920s due to its luxury hotels like the Principe di Piemonte, the Grand Hotel Royal and Hotel Plaza e de Russie on one side of the long promenade. On the other, designer shops back onto beach clubs lining the 20 kilometres of golden sands stretching beyond Viareggio to towns attracting Italy’s beautiful people, like Forte di Marmi.
Viareggio’s beach clubs, with names like Nettuno, Guido, Milano, and Amore, keep its beach organised, with swimming pools, bars, restaurants, and row upon row of deck chairs beneath colourful stripy umbrellas. And, sporting a fanciful array of stylised signs in Art Nouveau fonts, they play their part in maintaining the town’s architectural heritage.
And for me, this was much of Viareggio’s seduction. It was more than a seaside escape, with style and character far beyond that of many of Europe’s other coastal resorts. It was a pleasure to stroll its long promenade, the town’s buildings wrapping you in its colourful, early 20th-century heritage.
That evening we headed to the marina for dinner at L’Oca where we discovered two of Viareggio’s other attractions.
One of Italy’s great shipbuilding towns, it draws yachties seeking a fashionable port of call and those looking for their next superyacht. And, over a dinner of burrata ravioli with lobster sauce and locally caught fresh seafood, with fried courgette chips, we enjoyed the fruits of the yachties’ playground.
10 more places to see in Tuscany – small towns for your travel itinerary
The region’s bigger towns are often placed centre stage on a Tuscany travel itinerary, but it is a region that also boasts many great small towns and villages.
So deserving are they of your attention that many have been awarded the Bandiera Arancione – a tourism quality mark awarded by the Italian Touring Club. It acknowledges small villages and the best towns in Tuscany, distinguished by landscape conservation, the promotion of their culture and heritage, the quality of their accommodation, good food and a welcoming atmosphere.
So without further ado, here are some smaller towns to visit and the best places in Tuscany for when you’ve explored the region’s bigger, well-known cities.
Perfectly placed from its hillside perch to reach both Siena and Arezzo, Cortona is the epitome of those Under the Tuscan Sun dreams and one of the most popular places to see in Tuscany. While the town has crumbling piazzas and beautiful baroque church of San Filippo Neri to explore, you’ll also enjoy the panoramic views from its walls of olive groves and miles of the archetypical Tuscany countryside dotted with cypress trees.
Looking to escape the crowds? Anghiari is one of the best towns in Tuscany for an escape. It is set in the wonderful landscape of Valtiberina, an area which sees few tourists compared to other parts of Tuscany. On the approach to Anghiari, there is a point in the road where you can be struck by the view of the town as it comes into view from a hairpin bend.
Nestled between the Val D’Orcia and Val di Chiana, Montepulciano is a quintessential Tuscan medieval village, famed for its light red wine. Surrounded by a landscape of rolling hills, it has castle walls and ramparts, plus thermal springs.
Castelnuovo di Val di Cecina
Enveloped by oak forests, this small town is off the beaten path, which makes it the perfect place to enjoy an unspoilt Tuscan town.
Head south in the region and you’ll find Massa Marittima just north of Grosseto, in southern Tuscany. With medieval buildings topped with red roofs, it has a lot in common with the small towns of northern Tuscany making it a unique place to see in Tuscany’s Maremma area.
Small, but one of the best towns in Tuscany, Pienza is famous for two reasons – firstly for being the capital of pecorino cheese and next for being a UNESCO World Heritage Site.
Hidden away high in the Appenine hills, Barga is a must-see. Another medieval town, it is dominated by views of the Pania della Croce mountain in the Apuan Alps.
In the southern area of Chianti, Castelnuovo Berardenga dates back to the 1360s and developed as Siena’s stronghold due to its strategic position on the border of the Sienese region.
Certaldo is a beautiful little town perfectly located between Siena and Florence. Dating back to the Etruscans and the Romans, it is a great place to enjoy Tuscan food especially during the Boccaccesca Festival held between September and October.
Carved from volcanic stone, Pitigliano is one of the most charming towns in southern Tuscany. Here you can find Bronze Age, Copper Age and Neolithic remains. It also has a Medici aqueduct in the centre of town and a lovely Jewish neighbourhood.
Where to stay in Tuscany – we recommend…
Wondering where to stay in Tuscany? Here are my recommendations in some of its cities, on the coast, and in the countryside – whatever your preferred option, or favourite destination, there’s luxury accommodation to suit below.
City: rooms with views in Florence
The former residence of the Carrega Bertolini Princes, Grand Hotel Baglioni is a beautiful luxury hotel in with spectacular views of Florence from many rooms and suites, as well as from its B-Roof Restaurant which serves breakfast, as well as Tuscan dishes during lunch and dinner. The dining area and terrace offer views of the dome of the cathedral, Santa Maria del Fiore and Giotto’s Bell Tower.
Its elegant rooms are furnished in Florentine style with parquet floors, high ceilings and wooden beams.
Hotel Brunelleschi is set in a restored Byzantine tower and medieval church and has spectacular views over Florence’s cathedral. Decorated in a contemporary style, it has Osteria della Pagliazza serving local cuisine and gourmet restaurant Santa Elisabetta. Plus if you’re really taken by the hotel you can learn more about it’s history in its museum.
Coast: where to stay in Viareggio
In Viareggio I stayed at the five-star Grand Hotel Principe di Piemonte, one of a number of luxury hotels hugging this glistening coast.
The Principe di Piemonte is a five-star hotel with a spa, rooftop pool and sun terrace, a traditional Tuscan restaurant and the two Michelin-starred Piccolo Principe with panoramic views of the coast.
Its 106 rooms and suites are decorated in a different style on each floor. There’s 18th century French, Art Deco, empire, colonial and modern styles. I was in a colonial room, where Indian inspired fabrics hung at the windows and in a canopy over my bed, plus there was an exotic leather-covered the chair.
BW Premier Collection Grand Hotel Royal – the grand dame of this section of coast, the Grand Hotel Royal is a Viareggio landmark due to its Art Nouveau style with turrets and elegant interiors. Rooms are beautifully furnished, some with original tiled floors.
Hotel Plaza e De Russie is another historic residence built in Art Nouveau style in 1871 and is home to popular one-Michelin star restaurant, Lunasia.
Where to stay in the Tuscan countryside
There are hundreds of hotels, villas and more where you will be able to fall in love with Tuscany’s countryside. But I adored Castel Monastero, 24 kilometres from Siena.
The five-star superior hotel inhabits a renovated 11th-century monastery near Castelnuovo Berardenga. But Castel Monastero is far removed from the spartan existence of its early residents. My suite had exposed wood beams, terracotta floors, leather sofas, and a sumptuous bed.
But the hotel really comes into its own outside the rooms – Castel Monastero’s buildings, oozing character and history from its wishing well to its bell tower. Located on a vineyard, alongside views of the vines, Castel Monastero produces its own wine including a Chianti Classico. There is also a spa with a steam room, sauna and various whirlpools, a saltwater therapy pool in which you can float away your cares in mineral-rich water, plus it has wellness programmes with a focus on weight-loss, detoxing and rejuvenation.
Another stand out feature is its food. It has a Gordon Ramsey restaurant, Contrada, serving his take on gourmet Tuscan and Italian cuisine. Dining there is pretty special. I had a tasting platter of starters, lobster with tomato gazpacho, pecorino cheese ravioli, catch of the day brined in salt and rosemary, and Neapolitan baba with rum, lime cream, black cherry and Strega liqueur ice-cream.
But where Contrada served up a modern take on Tuscan food, the hotel has another restaurant La Cantina, serving more traditional dishes, in a vaulted 13th-century cellar.
There, executive chef, Nello Cassese gives cooking demonstrations. He whipped us up a pappa pomodoro made with different varieties of tomatoes and bread, plus perhaps the most famous of Italian desserts – tiramisu.
They were, naturally, delicious! Castel Monastero is a treat for mind, body and soul, and a perfect place to wind down in the Tuscan countryside.
Search for great luxury travel deals on places to stay in Tuscany
Tours of Tuscany
As this article no doubt attests to – there are very many things to see in Tuscany, and it can be difficult knowing where to begin when putting your trip together. So you might want to consider booking with a tour operator. I travelled to Tuscany with Citalia and was impressed by its offering.
In just five days I experienced much of its culture from its regal cities to its stylish coast and perfect countryside while enjoying wine and good food.
I am usually more inclined towards independent travel – putting together flights and hotels to create my own holiday. But by handing it over to the experts – Citalia has 85 years experience of travel in Italy – I was able to enjoy a much more immersive experience, in just a few short days.
Plus there were other services I wouldn’t usually have – a driver and luxury car at my disposal, city tours to get to grips with the likes of Florence and Siena. There were also local concierges – Dany in Viareggio, Caroline in Florence, and Amanda taking care of the countryside – on call for any query or with suggestions to make sure I made the most of my visit. But you can also be well armed with information before you travel.
Citalia Secrets is a service available to all Citalia customers to give them extensive insights into their destination. It includes restaurant and entertainment recommendations, tips, and need to know information. For me it was a hassle-free, well-informed way to get the most from my trip, and I left Tuscany with many, many wonderful memories of truly Tuscan experiences I wouldn’t have had without expert insights.
Places to visit in Tuscany – map of the region’s highlights from city to country and coast
More Tuscany tips
- Tuscany is a great place to visit throughout the year, but the best time is either spring or autumn when temperatures are most comfortable.
- International flights arrive into Florence and Pisa airports.
- Looking for yet more information on Tuscany? The Visit Tuscany site has yet more attractions from this fantastic region of Italy.