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Tuscany in May: 5 reasons to visit Tuscany in May

Claire Gordon • March 27, 2025

Thinking of visiting Tuscany in May? Enjoy our top five reasons to holiday in Tuscany in May.

Choosing to visit Tuscany in May is something you certainly won’t regret. While we love this magical Italian region at any time of year, the spring months are a real treat in Tuscany. For years, our Bookings For You guests have been enjoying villa holidays to Tuscany in May and for just as many years they have been telling us how wonderful it is. We too have sampled a few trips at this time of year. Whether its the city charm of Florence or the iconic vineyards of the Chianti hills, Tuscany in May is the perfect place to relax and soak-up the early Italian sun, before the summer season begins.

Tuscany in May

1. Fewer Crowds and More Charm in Tuscany in May

Tuscany is one of most visited regions in Italy. And while we agree that this is for very good reason, it does mean that very often you can feel that you’re sharing your slice of Italian paradise with more people than you’d like. If you plan to visit Florence or Pisa during July and August you will literally be rubbing shoulders with fellow visitors. Even in the countryside and at the beaches, it’s often a struggle to find parking. And you may well grow weary sightseeing in soaring temperatures.

However, visiting Tuscany in May makes for a much more enjoyable experience. Not only will there be fewer visitors but, without the crowds, Tuscany’s true charm can really be experienced. While we love the buzz of a bustling Italian piazza, we also enjoy being spontaneous when on holiday. It can be tiresome to have to book restaurants weeks in advance. During the high season, days and dinners out take planning which can sometimes be difficult to do from home. What’s great about visiting Tuscany in May, is that such planning isn’t necessary. Restaurants tend to be less busy and even in the centre of Florence you can often get a table without a reservation. Likewise, tours and activities are much easier to organise during shoulder season.

Tuscany in May

But more than any of this, what we love most about visiting Tuscany in May, is the space to breathe. If you haven’t been to Tuscany before, it’s really difficult to describe just how beautiful this region of Italy is. From the iconic cities of Florence, Pisa and Siena, to the vast rolling vineyards of the Chianti hills, Tuscany deserves space and time.

Discover our stunning collection of Tuscany villas >>>

Tuscany in May

2. Spring Flowers and Vibrant Vistas

Spring brings sunshine in Italy. Typically, in May, Tuscany sees daytime temperature rise to just above 20 degrees and there are 15 glorious hours of daylight to enjoy. With this renewed warmth comes the arrival of an abundance of glorious spring flowers and colour is once again restored to the region’s iconic vineyards. In fact, in Tuscany in May, the hills are alight with almost every shade of green and it’s the perfect time to enjoy a tour or tasting.

Tuscany in May

Tuscany is the true definition of natural beauty. And while there are some stunning shows of manicured gardens and flowers to admire in Tuscany’s towns and cities, it’s wild flowers that take centre stage in Tuscany in May. Poppies create red carpets fit for the finest film stars and every hedgerow is filled with natural fiery blooms. Purple irises spring up, creating a stunning contrast with the vibrant green environment. In Florence, the annual Giardino dell’Iris opens to the public. Here there are thousands of varieties of Tuscany’s most symbolic flower to admire. Meanwhile in the Val D’orcia hills, landscapes are painted yellow with the arrival of the rapeseed crop, interrupted with cotton-like white-spring blossom – a dreamy destination for photographers.

If you’re keen on keeping active, May is an excellent time to enjoy the marvellous hiking and adventure sports that Tuscany has to offer. Most people don’t realise that Tuscany is home to some magnificent mountains. And while this region is most famous for the rolling hills of Val d’Orcia, Tuscany also has some impressive peaks, marble quarries and even a few volcanos!

Tuscany in May

3. Festivals and Events in Tuscany in May

It’s certainly no secret that Italians love a festival. Throughout the year every region in Italy hosts a festival for almost everything you can think of. We can assure you that in Tuscany in May you will be spoiled for choice when it comes to events and festivals to keep you entertained. Here are a few of the highlights.

Cantine Aperte

Wine lovers will find a trip to Tuscany in May a real treat. This is when Cantine Aperte (open cellars) begins. This is a region-wide event which sees wineries across Tuscany open their doors for visitors to enjoy tours, tastings and to also meet the winemakers themselves. Most tastings also include a spread of traditional Tuscan antipasti. It’s not unusual to have meats and cheeses all sourced from the same farm. A truly field to fork (and glass!) experience. What’s more this is also the perfect opportunity to pick up a few treats to take home.

Tuscany in May

Maggio Musicale Fiorentino

In Florence, the whole month of May is dominated by the city’s iconic Maggio Musicale Fiorentino. This is a celebration of the arts with opera, concerts and all kinds of theatre performances taking place. While the event is attended by music lovers from all over the world, it has still managed to retain an intimate and truly authentic Italian feel. What we love most about this event is the way the whole of Florence immerses itself in the festival. Spend a day wondering the city’s ancient streets and finish with and evening performance in the Teatro del Maggio.

Tuscany Medieval Festival

If you fancy stepping back in time then there is also no shortage of events to whisk you away to medieval Italy. One of our favourites is the Tuscany Medieval Festival in Livorno. Join more than 150 re-enactors who who take part in shows, battles and duels. Knights on horseback gallop through the ancient streets with music from drums and historical instruments providing the soundtrack for this fabulous show of events. There are also banquets and feasts (this is Italy after all!) so you can even get a taste of the middle ages.

Tuscany in May

Infiorata di Scarperia

May also marks the start of flower festival season in Tuscany. One of the most impressive shows is the Infiorta di Scarperia. This charming village transforms itself into a majestic carpet of flower-art made with the petals of hundreds of thousands of flowers. It’s a magical sight and a wonderful excuse to explore Tuscany’s smaller, less visited villages.

Chianti Hills Marathon

Finally something for the active travellers, May sees the Chianti hills host its annual marathon. While many of us may not immediately think of  running a marathon when we think of a holiday in Tuscany, this event is becoming more and more popular. The organisers now offer a classic route, an ultra 53KM option for the super-fit and also a 10KM walking route. This is a very original way to see some of the most sunning Tuscan landscapes and there is arguably no better view for a run. However, what we love most about this event is the celebratory lunch held after competitors have finished the race – very Italian!

Tuscany in May

4. Perfect Weather in Tuscany in May

Weather-wise, May is possibly the best month in which to visit Tuscany. The sky is postcard blue, the sun is high and the days are long. But, the sometimes oppressive heat of the summer months is yet to arrive. And while the weather in Tuscany in May is warm, the humidity remains relatively low. Daytime temperatures usually range between 20 and 25 degrees which makes it perfect for al fresco dining. And even the evenings can be warm enough to star gaze above the rolling Chianti hills.

Tuscany in May

What’s more these mild but kind temperatures, make exploring Tuscany much more pleasant. Florence’s iconic landmarks are much better visited at this time of year. The same is true for the tower of Pisa and Tuscany’s magical hilltop towns and villages. Equally the endless hiking and cycling opportunities are far more enjoyable in the spring sunshine. And with an average of 10 hours of sun and 15 hours of daylight, Tuscany in May is just perfect for relaxing too.

5. Affordable Luxury in Tuscany in May

We often choose to visit Tuscany in May for all the above reasons. However, one of the real bonuses of taking a trip at this time of year is that is also a great time to snap up some serious luxury at a much more affordable cost. Here at Bookings For You, we have been preaching for years about the value in opting for a villa in Tuscany as opposed to a hotel package. Not only do you get a more authentic experience but also the freedom and space we think every visit to Tuscany deserves. And by choosing a villa holiday in Tuscany in May you can stay in a wonderfully luxurious place, for a fraction of the coast of the summer months.

Tuscany in May

Our top choice for great value luxury in a villa in Tuscany in May is Villa Rossa. Sleeping up to 16 guests, Villa Rossa has its own private pool and extensive gardens to enjoy outside. But, even if the weather is unfavourable, you can still relax indoors in the villa’s private wellness and relaxation area – complete with sauna and plunge pool. Not only that though, Villa Rossa is situated in the Upper Valdarno, one of the most beautiful areas of Tuscany. You may recognise it as being captured in paintings by Leonardo da Vinci amongst others. And all of this could be yours for just £40 per person per night in May.

Tuscany in May

Looking for help with accommodation in Tuscany? Contact our Italy experts at Bookings For You for help finding your perfect place in Tuscany in May or at any time of year. Or discover our full collection of stunning Tuscany villas here.

Tuscany in May