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May in Tuscany: food, wine, crafts and flowers

April 6, 2020 UPDATE: Since Italy continues to be on FULL LOCKDOWN, all events are cancelled. A few have been delayed and planned for summer dates but whether those will take place will be seen further on. The information on the page below has not been updated. Stay safe!

Maggio, Maggio canto i colori,
riempio i giardini e i prati di fiori;
tutto è più bello e profumato
ed anche il bosco si è risvegliato.

The Tuscan tradition praises the colors and blossoms of May, and while the weather can still be temperamental, that doesn't stop all the fun and activities throughout the region of Tuscany: along the coast, in the hills, from small town to small town there is something for everyone.

If you happen to be in Tuscany during this period - which is one of the best times of the year for visiting Tuscany - you 'll find long daylight hours, warmer temps and lots of outdoor activities for everyone. You 'll be challenged to decide between all of the food and wine festivals, antiques and handicrafts exhibits, and adventures!

Many of the events taking place throughout the month celebrate the region's traditions and ancient customs, check out a complete calendar of Medieval Fairs and May Wine Events.

Are you ready to find out the most important among them?

Author's Note: This article was last updated on January 29, 2020, to make sure we're giving you up-to-date info, if the dates have not yet been announced then we indicate TBA (to be announced). If they have not yet been posted keep checking in with us...or better yet, write us on the Forum


Italy | FESTA DEL LAVORO | May 1st

Italian Labor Day

The first article of the Italian constitution states: "Italy is a democratic republic, founded on work". Therefore the Italians have declared it a national holiday and (at least in theory) should be able to celebrate by not working! Beware that public transport schedules will be “festivi” and not run as often as on a normal workday.

Italy | GIORNO DELLA MAMMA | 2° Sunday in May

Italian Mother 's Day

For all of those traveling with their Mom in Florence on May 13th, remember to give her an extra hug and wish her Happy Mother 's Day, Italian style of course...that means a double scoop of gelato!


Arezzo | FIERA ANTIQUARIA | 1° Sunday (and proceeding Saturday) of every month

The oldest and the biggest antique fair

Many years ago, Ivan Bruschi gave life to one of the oldest and biggest antique fairs in Tuscany...maybe even all of Italy. He transformed his love for the old, unique and precious into an event that fills the streets of Arezzo every first Sunday of the month and the Saturday that precedes it that month. So mark your calendars for May 5 & 6th - and be sure to leave some time to explore the museums and churches Arezzo.

Official Site

Greve in Chianti | IL PAGLIAIO | Every 4th Sunday of May

Organic and Artisan Market

Piazza Matteotti is the heart of Greve and it bubbles over with locals displaying goods from their gardens, their kitchens, and their workshops. Often you will find great bargains, music, and opportunities to do some taste testing.

Facebook Page

Panzano in Chianti | APRILANTE | 1st Sunday in May

Handcrafts & Vintage

We know they call the fair "April"-ante, but it really goes all year round! This monthly market in the streets of Panzano, a charming town in Chianti is where you will find handcrafts, vintage and delicious typical foods and all of it this is just outside in the countryside surrounding Florence.

Official link

Markets in and Around Florence May 2019



44 Years in Valtiberina

Being its 44th year, the exhibition in the Tuscan Valtiberina - will be held in Anghiari until May 1. A fair that brings together the old and the new, old skills and trades with new methods, artists and designs.

Official Web page

Events and activities in Tuscany this May

Querceta | PALIO DEI MICCI | 1° Sunday of May

Donkeys make up the fun along the coast

In this little fraction of Forte dei Marmi in Versilia, on the 6th of May, you will find a traditional donkey competition. The goal: the first donkey that surpasses the others will win the race (every donkey represents a contrada of Querceta). Every year, this hilarious show draws lots of people who eagerly await to see the stubborn and disobedient animals trying to win the race. A historical parade with more than 2000 people dressed up in costumes will wind its way through the town streets.

Official Web page

Events & Activities in Tuscany this May

Bagnone | SAGRA DELLA CIPOLLA | May 1, 4 & 5, 11 & 12

In the shadow of the Castello

Enjoy a delicious food festival based on local recipes for the Treschietto onion; a culinary festival dedicated to a particular variety of onions which have been cultivated in this territory for many years. The Treschetto onion, distinguished for its flattened shape, the ruby red color on the outside and white with red streaks on the inside, it is the main Ingredient both cooked and raw in many dishes. Come out and try a few. (The fair opens on Saturdays open from 5 pm and on Sundays from 12 noon).

Official Web page

Events and Activities in Tuscany May 2019

Montalcino | TRENO NATURA | May 1

Slow Travel in Southern Tuscany

A trip exploring the Montalcino area and welcoming the beauty of spring in this UNESCO heritage site. Departing from Siena and passing through Buonconvento to visit the scenery and markets of Southern Tuscany. Meet your train in Siena and visit the incredible landscape in slow motion aboard a vintage steam engine for the ancient flavors during the market day in the famous Crete Senesi.

Check out our blog post with more details on the Treno Natura program in English.

Events and activities in Tuscany this May

Porto Ercole | NOTTE DEI PIRATI | May 3 - 5

Avast Ye! The Pirates Have Landed in Tuscany

The first weekend of May, the countryside changes and becomes even more picturesque and mysterious. A transformation involving the promenade and its beaches, and especially bars, restaurants, locals and ... people. Costumes and choreographed scenes provide every edition new fun and entertainment motifs for "pirates" and spectators.

Official Web page

Events & Activities in Tuscany this May

Pisa | FOOD ART ITALY | May 3 - 5, 2020

Looks good? Then it has to taste good!

Just in time for Spring! For those who love good food, understand the importance of the art of “presentation”. This fair in Pisa will highlight 4 sections - each connected to the beauty of the presentation: Food, Wine & Beer, Restaurants, Professional Equipment, Cake Design.

Official Site

Pieve Santo Stefano | SAGRA DEL PRUGNOLO | May 4

Special Editions

Located in the province of Arezzo and one of the most eastern towns of Tuscany, this small town features a festival for the foodies; an event you won't easily forget. This magical mushroom is said to grow on the night that the witches dance, and its flavor is reminiscent of fresh flour and truffles. Not only will you find a yummy menu but also an event that celebrates the shepherds and the “transumanza”, when they would herd their sheep towards the green grass of the Maremma

More Info

Events & Activities in Tuscany this May

Borgo San Lorenzo | Mugello Wild | TBA

Exotic Animals & Plants

This special little town in Mugello opens its doors to the special and exotic with a market, falcon shows and information on the wide range of wildlife. Mixed in with the medieval setting, you will find an exciting atmosphere.

Official Site

Terricciola | FESTIVAL DELLA FRAGOLA | May 4 - 5 & 11 - 12

36 years celebrating Tuscany 's Favorite Springtime Fruit

Two full weekends of strawberries! And not just this delicious sweet red fruit but also music, fun and hopefully some warm sunshine. Be sure to stop in get a cup of sweet goodness and join 1,000's of locals who come to celebrate the beginning of spring.

Official Webpage

Montieri | SAGRA DEL PRUGNOLO | 2° Sunday of May

Mushrooms are spring up everywhere

From east to west in the region of Tuscany everything's coming up mushrooms, last weekend you might have seen the festival in Pieve Santo Stefano, and this week in the countryside between Siena and the coast. During the 12th & 13th of May in Montieri, you can taste the exquisite springtime mushroom Prugnolo. From cheeses to liquor, plates of pasta and delicious meat dishes, everything is based on the Prugnolo mushroom! In addition to the food, the fest offers markets, local products, music, and hikes.

More Info

Events, sagras and activities in Tuscany this May

Calci | GIOCO DEL MULINO | 2° Sunday of May

Donkeys and Laughter along the coast

In the province of Pisa, the little town of Calcio will divide amongst itself in fun and games on May 13th. The rioni (quarters) of the town will compete against each other pushing a mill 's wheel towards the river. The wheel, once established at the arrival point, will decide the winner (and loser), who will be thrown some wheat as a compensation prize.


Events and activities this May in Florence

Asciano | TRENO NATURA | May 13

Slow Travel in Southern Tuscany

A trip to Asciano departing from Siena to visit the landscapes and markets of Southern Tuscany. Meet your train in Siena and visit the incredible landscape in slow motion aboard a vintage steam engine for the ancient flavors during the market day in the famous Crete Senesi.

Check out our blog post with more details on the Treno Natura program in English.

Events and activities in Tuscany this May

Gaiole in Chianti | POLVERE & GLORIA | May 17 - 19

Motorbike Rally along the Eroica Route

Dust&Glory is a motorbike rally along the route of the Eroica, 200 kilometers of half paved and half dirt roads, through the most beautiful spring Tuscany landscapes. Welcome to "Dust&Glory – on the streets of the heroic© in motion ", the only official: a path of 208 km asphalt roads half half immersed in the most beautiful part of Tuscany; the atmosphere of a real “Rally” and the friendship that only among bikers can enjoy, benchmark for enduro and tourist must in particular for lovers of “vintage”, not to mention the kitchen! This edition introduces the “Zero +” category, dedicated to electric motorbikes. It will go alongside the two traditional categories “Vecchie Glorie”, (bikes registered and validated before December 31st, 1999), and “Saranno Famose”, (registered from January 1st, 2000).

Official Webpage

Montecarlo | VIAVINARIA | May 18 & 19

Catch the Wine Bus

A totally unique event that has you touring the countryside around this stupendous little town and tasting the DOC wines. Let Montecarlo take the wheel as they drive you from Cantina to Cantina, showing off their particular recipe for great wine. t will also be possible to visit the village for free with its medieval architecture such as the Fortress of Cerruglio, the splendid Teatro dei Rassicurati, the Collegiate Church of S.Andrea Apostolo, true treasures of the artistic and cultural heritage of Montecarlo.

Other Fun Wine Events in May

Torrenieri | TRENO NATURA | May 20

Steam Engine in Southern Tuscany

A totally romantic and epic what to visit the scenery and wines of Southern Tuscany. Meet your train in Siena and visit the incredible landscape in slow motion aboard a vintage steam engine.

Check out our blog post with more details on the Treno Natura program in English.

Events & Activities in Tuscany this May

Cascina | PALIO DI SANTO STEFANO | 2° Sunday of May

Steam Engine in Southern Tuscany

Every second to last Sunday of May (May 21 this year) Cascina is home to the Palio di Santo Stefano, commonly known as the Palio of the Bridge, even if this is not as famous as the one which takes place in Pisa in June. Eight groups - with 8 members each - push a large cart set up on the bridge on rails. The aim of the game is to conquer the enemy 's side and win the competition. And don't forget to stop and taste the local specialty at the Sagra of the Eel, held at the same time.

Castelfranco di Sotto | PALIO DEI BARCHINI | 3° Sunday of May

Rowboats with no water in sight

Silly yet fun! In honor of the traditional "renaioli" who would drag the bottom of the Arno river, pulling sand and stone to keep the river clean and passable as well as providing important material for the construction of buildings in the area. Just watch out for the boats with wheels as the race around this little town located along the Arno River between Florence and Pisa.

Pieve a Nievole | ON THE ROAD | May 25 - 27

The Best of the Best prepare the Menu

The trend is street food, and this festival brings you the best from all over Italy combined with music and festivities. Fifteen chefs have been selected to travel with the Food Art Italy. In addition to great food, there will be space dedicated to live music, DJ sets, and entertainment. It starts Friday, May 25 at 9 pm with the rock music of "On Air". Saturday, May 26, the evening will be dedicated to the legendary Rolling Stones, thanks to the sounds of the tribute band "Wild Rose" and Sunday, May 27th, great performances and dancing with DJ sets.

Facebook Event

Montalcino | L 'EROICA PRIMAVERA | May 27

Biking 117km of Brunello

Cyclists on the white roads of Tuscany; there are four trails departing from Montalcino and stretching to the Val d'Orcia, passing through Bagno Vignoni, San Quirico d'Orcia, Pienza and the heart of the Crete Senesi with Montisi and Trequanda. During the day you can enjoy the magnificent views, small towns, and some serious exercise and at night the streets of the borgo (town) will be lit up for a festival immersed in the charm of the medieval streets.

Official Webpage

Lucignano | MAGGIOLATA | Last two Sundays in May

Over 80 years of the Maggiolata

The Maggiolata Lucignanese traditionally takes place the last two Sundays in May and has been doing so for more than the last 80 years. This year Lucignano you will find a parade of flowered wagons animated by groups in peasant costumes on, with special activities on other evenings in May. Each float represents a different “rion” or district of the town, performing in choreographic movements and songs of folk tradition or composed specifically for the festival by local poets and musicians.

Official Website

Events in Tuscany this May

San Casciano Val di Pesa | TERRE di MAGGIO | May 26 & 27

Flowers are Blooming again in Chianti

The historic center of this charming little town in Chianti will be filled with roses, aromatic plants & herbs, and many other colorful blossoms. Stores and the main squares of San Casciano V.P. will be open even on Sunday with artistic displays, local products, animal shows, and delicious treats. Sunday you can participate in the fun and exciting lawn mower race - choose your town and cheer them on!

Facebook Page


The Cherry Capital in Tuscany

Lari is commonly referred to as the town of cherries: it is the most renowned and important place in Tuscany for cherry production. It will be hosting the Cherry Festival, a delicious event dedicated to this tasteful fruit, abundantly cultivated amidst the rolling hills that surround the town of Lari.

Tuscany Wine Cellars | CANTINA APERTA | May 26 - 27

Bring your tastebuds & wine glasses

This special event includes the opening of many famous and not so famous vineyards throughout Tuscany. Surprises everywhere with wine tasting, food, and tours of these interesting areas. Read here for more information on this event.

Click here to find who is open

Events & Activities in Tuscany this May

Chiusi | TRENO NATURA | May 12, 19 & 26

Slow Travel in Southern Tuscany

A trip to Chiusi starting in Siena to visit the landscapes and markets of Southern Tuscany. Meet your train in Siena and visit the incredible landscape in slow motion aboard a vintage steam engine.

Check out our blog post with more details on the Treno Natura program in English.

Events and activities in Tuscany this May

Peccioli | TUSCANIA FESTIVAL | May 18 - 19

The medieval streets of Peccioli will be filled with artists, musicians, performs and their ideas. This is the Tuscania Festival, a super festival celebrating “creativity”, a special event in Tuscany where everyone is invited to add to the fun.

Web Page

June Events and Activity calendar in Tuscany

Buggiano | SGRANAR PER COLLI | May 29

It is a 10km walk through some of the most hidden trails of the Buggiano territory, with stops in the three main hills of the municipality: Colle - Buggiano - Stignano. Along the route and at the same time the participants will be able to taste and taste local produce: wine, oil, jams, honey, cheeses and other delicacies of our culinary tradition. Official Website

Events & Activities in Tuscany this May

Author: Donna Scharnagl

It has been more than 25 years since I took my first steps in Italy and I still haven’t found a good reason to leave.  Between the food, the culture, the history, the art, the landscapes … did I mention the food? I have become a lifelong student. It didn't take long to learn that Italians all have stories that long to be told; stories that paint a picture of how hard work produces character, how life is made of ups and downs and how good it feels to laugh.


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