Tuscany, a beautiful region situated in the central-western part of Italy and spanning inland, is renowned as the birthplace of the Renaissance. And while it’s a destination on many a travel bucket list, you may be wondering whether visiting Tuscany in May is the best idea.

Magnificent wineries, delicious cuisine, and stunning landscapes are some of the main reasons tourists choose to visit Tuscany in May. With a range of outdoor activities, cultural experiences, and museums, along with fewer crowds than in summer, there’s something for everyone in Tuscany during the end of the spring season.

If you’re considering a trip to the heart of Italy in May and need help planning your trip, fear not, as we’re here to help. Continue reading to find out all you need to know and more!

Weather in Tuscany in May

Tuscan landscape in a cool evening of May
Tuscany in May: the evenings can be quite cool

By May, spring is in full swing, and while the weather can be unpredictable, it tends to be more stable with fewer rain showers and longer periods of sunshine. 

Daily temperatures usually range from 54°F to 73°F, with occasional highs reaching 86°F. In coastal and lowland areas, temperatures typically average around 59-70°F, while in the mountainous regions and hills of Siena, the climate is cooler.

We highly recommend packing a combination of shorts and t-shirts alongside windbreakers and sweaters to prepare for the cooler evenings.

Explore more: Tuscany in Spring – A Comprehensive Guide for a Memorable Trip

Is Tuscany Crowded in May?

Visiting Tuscany in May is a great idea, as it’s just before the peak season starts.

During this time, the region hosts various festivals and events. However, even though it’s less busy than in summer, we highly advise booking everything in advance to avoid any inconvenience.

What are the Best 7 Things to Do In Tuscany in May?

1. Visit the City of Florence

Florence in a warm day of May
Florence in May can be very warm, but usually not crowded like in summer

The capital city of Tuscany, Florence, is famous for its Renaissance art and architecture. There are numerous activities to indulge in during this time, such as climbing to the top of the Duomo, admiring Botticelli’s masterpieces at the Uffizi Gallery, exploring the Galleria dell’Accademia, and taking a leisurely stroll through the Boboli Gardens to experience the ambiance of the 13th through 16th centuries.

Plus, when you visit Florence in May, you won’t have to deal with the hoards of summer crowds.

2. Visit the Wine Cellars of Montepulciano

Exploring an underground wine cellar is among the top things to do in Montepulciano. You can opt for a tour of some cellars, while others offer a tour coupled with a wine tasting. Alternatively, you can choose to savor some wine in the cellar itself.

De’Ricci Cantine Storiche is one of the most renowned wine cellars in Montepulciano. Step inside, and you’ll be greeted with vaulted ceilings and walls of enormous wine barrels. 

Just make sure to book a tour and wine tasting in advance if you want to make the most of your trip!

3. Pienza e i Fiori 

Pienza is a small town located in Val d’Orcia, known for its charming atmosphere and undulating landscapes. 

Though it’s a small town, it’s surprisingly accessible, perfect for those looking to check off every box on a fast-paced itinerary.

In May, you’ll get to experience the Pienza e i Fiori (Pienza and the Flowers) festival, which is a colorful celebration marking the arrival of summer. 

The origins of the festival go ways back, and many say it began as a ritual to honor the upcoming year’s harvest. Today, it’s a dazzling spectacle with bright flowers transforming the streets of the town throughout the month.

Explore more: Towns in Tuscany – Jewels of Italy’s Rich Culture

4. Notte dei Pirati in Porto Ercole

Porto Ercole in a summer May day
May is probably the best period to visit the seaside town of Porto Ercole – Photo by fabulousfabs CC BY-NC 2.0

One of the most highly anticipated and well-attended occasions in Argentario is “The Night of the Pirates.” This event occurs on a weekend in spring in Porto Ercole, a quaint village situated in the southern part of Monte Argentario.

This festive event combines local folklore with playful activities, though it also has deep roots in the history of the region. 

Over the years, it has become an extremely popular tourist attraction, providing visitors with a unique opportunity to explore the charming village of Porto Ercole and the surrounding Argentario area. 

During the event, the streets are adorned with pirate-themed decorations, and many participants dress up in pirate costumes, transforming the village into a pirate’s den.

5. Fish and Wild Boar Festivals in Certaldo

If good eats are in the cards, head to Certaldo for the fish and wild boar festivals.

For starters, we have the Wild Boar Festival in Certaldo, which has a rich history dating back four decades. The festival began as a way for hunters to share their bounty and gather together to enjoy a meal of wild boar, prepared by their wives, accompanied by new wine and a festive atmosphere.

There’s no better chance to try delicious wild boar!

The Fish Festival is another well-known local event that takes place in Certaldo, running from mid-May to mid-June each year. The festival is a food lover’s paradise, with many food stalls lining the streets, offering various traditional and local delicacies, including the renowned Tuscan fish soup known as “Cacciucco alla Livornese.”

6. Visit San Gimignano

The central square of San Gimignano, in Tuscany
Don’t miss San Gimignano if you visit Tuscany in May

San Gimignano is a must-visit Tuscan town with dramatic landscapes and a unique hilltop location. It is famously known as Italy’s Medieval Manhattan, thanks to the skyline of 14 stone towers that rise dramatically from the Tuscan countryside. 

From climbing the Torre Grossa to sipping on Vernaccia di San Gimignano, there’s plenty to enjoy!

Explore more: Tuscany In April – Things To Do, Events To Attend, and More

7. Cantine Aperte

Cantine Aperte is one of the most talked-about Tuscan spring festivals, attracting tourists and locals alike.

This festival of wine got its start back in 1993, showcasing wine producers and teaching visitors about the winemaking process. It’s a great event for anyone who wants to learn more about the passion and intricacy that goes into making a bottle of wine!

Best Hotels in Tuscany in May

Let’s explore some of the best hotels for a trip to Tuscany in May.

Luxurious Hotel In a Castle

Elegant room and relaxing atmosphere in Castello di Casole, A Belmond Hotel, Tuscany
Photo Credit: Booking.com – Castello di Casole, A Belmond Hotel, Tuscany

The Belmond Castello di Casole is a beautifully restored castle, featuring several elegant rooms, unparalleled gourmet dining, a spa, and stunning views of the Tuscan countryside.

Location: Localita Querceto, 53031 Casole dʼElsa, Italy

Stars: 5

Features: Outdoor swimming pool, Garden, Balcony

Reviews: 9.5/10

Ornate Villa Overlooking the Countryside

View of the Villa Cora during nighttime
Photo Credit: Booking.com – Villa Cora

Villa Cora is a grand villa hotel located in a park in Florence, delivering on all ends, from the luxurious pool to the relaxing spa to the restaurant with panoramic views.

Location: Viale Machiavelli 18, 50125 Florence, Italy

Stars: 5

Features: Outdoor swimming pool, Spa, Fitness center

Reviews: 9.2/10

Boutique Stays in the Heart of Pienza

Clean room in La Bandita Townhouse
Photo Credit: Booking.com – La Bandita Townhouse

The La Bandita Townhouse is a smaller hotel in the heart of Pienza. You’ll find a one-of-a-kind farm-to-table restaurant, a rooftop terrace with panoramic views, and a number of stylish rooms.

Location: Corso Il Rossellino 111, 53026 Pienza, Italy

Stars: /

Features: Very Good Breakfast, Spa, Restaurant

Reviews: 9.2/10

What to Wear and Pack in Tuscany in May

A young woman wearing outfit suitable for traveling to Tuscany in May
Outfit suitable for women to wear while traveling to Tuscany in May

For men visiting Florence in spring, we highly recommend packing a blazer as a stylish piece that can be worn to restaurants and on cooler days. As for bottoms, lightweight jeans and chinos are also recommended. 

Beyond that, short-sleeved t-shirts are great for daytime wear, while long-sleeved button-down shirts or polo shirts are great for evenings out. Make sure to pack a waterproof jacket to prep for rain as well!

Women can also follow the same basic idea. For bottoms, pack jeans, chinos, and lightweight trousers, and. opt for mid-length skirts and dresses for nicer outings. 

Both men and women should also make sure to pack comfortable shoes for walking around all day!

Of course, to fully enjoy your trip to Tuscany in May, it’s crucial to pack the right gear and essentials along with your clothing:

  • Sunglasses – Make sure to pack a pair of sunglasses when visiting Florence in May, as the weather can be quite sunny.
  • Sun Hat – Protect that beautiful face of yours on daily outings with a protective sun hat
  • Backpack – When traveling during the day, having a lightweight backpack to hold your belongings is key.
  • Camera – Want a way to remember your vacation in HD? Bring a quality camera!
  • Charging Cable Adapter – The last thing you want is to be stranded out at a rural winery because your phone is dead. Make sure you pack a charging cable adapter
  • Mosquito Repellent – Mosquito season generally starts in the warmer days of spring, so have some mosquito repellent handy.
  • Small Umbrella – As we said before, rain can be intermittent. It’s always a good idea to have a travel umbrella on hand!

Read more: Books on Tuscany – The Top 8 to Inspire Your Italian Adventure

Frequently Asked Questions about Tuscany in May

Is May a Good Time to Visit Tuscany?

May is a great time to visit Tuscany, as you’ll get to experience the vibrancy of the countryside without all of the hustle and bustle of summer tourism.

Is Tuscany Warm in May?

The weather is pretty comfortable in Tuscany during May. Daily temperatures usually range from 54°F to 73°F, with occasional highs reaching 86°F

Is Tuscany Busy in May?

While there are certainly many people that visit Tuscany from May through October, May is not the busiest month of the year.