If you are wondering about the best things to do in Tuscany and Umbria in May, you are choosing one of the most beautiful times of the year to visit Italy.

May is when the countryside comes alive: green hills, blooming flowers, longer days, and perfect temperatures. It is also the ideal moment for those looking for a slow travel experience in Italy, بعيد from crowds and closer to authentic local life.

In this guide, we share the best events, experiences, and hidden gems in Tuscany and Umbria in May 2026.

🗓️ Best Local Events in Tuscany & Umbria in May 2026

🍷 Cantine Aperte – The Best Wine Event in Tuscany and Umbria (May 30–31, 2026)

One of the top things to do in Tuscany and Umbria in May is without a doubt Cantine Aperte.

During the last weekend of May, wineries across Tuscany and Umbria open their doors to visitors.

You can enjoy:

• Wine tastings in historic cellars
• Vineyard walks in the spring countryside
• Food and wine pairings with local producers

This event is perfect if you want to experience Italian wine culture in an authentic and relaxed way.

Best Sunset Aperitivo at Madrevite Winery – May 1, 2 and 3+ May 17 and 17 + May 30 and 31.

https://www.madrevite.it/picnicco/

🌸 Early May Events

🛍️ Arezzo Antique Market (First Weekend of May 2026)

Arezzo hosts one of the most famous antique markets in Italy. If you love unique pieces, vintage objects, and local craftsmanship, this is one of the best things to do in Tuscany in May.

🌷 Festa del Tulipano – Castiglione del Lago (April 24 – May 2, 2026)

Overlooking Lake Trasimeno, the picturesque town of Castiglione del Lago bursts into color during the Festa del Tulipano, one of the most iconic spring events in Umbria.

It’s a beautiful and lively experience, perfect for a spring day by the lake. However, it’s worth noting that on Sundays — especially during parade days — it can be quite crowded, and parking may be difficult to find.

👉 https://festadeltulipano.com/

💜 Lavender Festival in Assisi  on May 1, 2 and 3 and 8, 9 and 10 

Every spring, just outside Assisi, the countryside transforms into a sea of purple during the Lavender Festival. 🌿 A truly sensory experience where you can: Walk through blooming lavender fields – Taste lavender-infused products – Discover local crafts and organic goods – Enjoy the peaceful atmosphere of the Umbrian countryside

👉 https://www.illavandetodiassisi.com/

🌸 Pienza and Flowers Festival (May 2–17, 2026)

In the heart of the Val d’Orcia, the enchanting village of Pienza transforms into a breathtaking open-air garden during the 39th edition of “Pienza e i Fiori.” The highlight is the stunning Renaissance garden set up in Piazza Pio II, where floral installations blend seamlessly with the town’s historic architecture.

Over two weeks, visitors can wander through blooming streets, enjoy the vibrant spring market on May 9–10, and experience “Flowers on the Plate” on May 16 — a unique culinary event where local chefs reinterpret traditional dishes with edible flowers and seasonal ingredients. It’s one of the most elegant and sensory ways to experience spring in Tuscany.

🌿 Montepulciano Agricultural Fair (May 2–10, 2026)

Set in the countryside just outside Montepulciano, the 42nd edition of the Fiera dell’Agricoltura brings together the authentic rural soul of Tuscany in the area of Tre Berte, in the heart of the Valdichiana.

Held on May 2–3 and again from May 7–10, this traditional fair is a lively mix of heritage and local life, where visitors can explore agricultural exhibitions, livestock shows, and displays of farming machinery and equipment. Alongside this, you’ll find equestrian performances, music, and plenty of opportunities to taste regional specialties.

🎈 Coloriamo i Cieli – International Kite Festival (May 1–3, 2026)

Set against the wide-open skies of Lake Trasimeno, Coloriamo i Cieli transforms the former Eleuteri airfield in Castiglione del Lago into a spectacular celebration of flight and color.

This historic international kite festival fills the Umbrian sky with hundreds of kites from around the world — from traditional handcrafted designs to breathtaking acrobatic displays. Alongside them, hot air balloons and aerial performances create a truly magical atmosphere.

👉 https://www.umbriatourism.it/en/-/colourful-skies

🎭 Calendimaggio Festival – Assisi (May 6–9, 2026)

One of the most beautiful historical festivals in Italy, Calendimaggio turns Assisi into a medieval stage. Locals dress in period costumes, and the town comes alive with music, performances, and competitions between districts.

👉 https://www.calendimaggiodiassisi.com/

🚗 Coppa della Perugina (May 7–10, 2026)

From May 7 to 10, the elegant city of Perugia hosts one of Italy’s most fascinating historic events: the Coppa della Perugina. Originally created in the 1920s by the founder of the famous chocolate brand, this iconic race is now a refined re-enactment featuring up to 100 vintage cars produced before 1965.

It’s one of the most unique ways to experience Umbria in spring — where vintage cars, slow travel, and Italian lifestyle come together beautifully.

👉 https://www.coppadellaperugina.com/programma/

Paciano Open Museum Week

🌿 Mid May Events

🔥 Corsa dei Ceri – Gubbio (May 15, 2026)

A powerful and emotional tradition dating back to the 12th century, the Corsa dei Ceri is one of Italy’s most authentic festivals. Three teams carry massive wooden structures through the streets of Gubbio in a breathtaking race up to the Basilica of Saint Ubaldo.

👉 https://www.umbriatourism.it/en/-/festa-dei-ceri-event

🎆 San Crispolto Festival – Bettona (May 11–12, 2026)

A small, authentic local celebration dedicated to the patron saint of Bettona. Expect processions, local food, and a festive village atmosphere—perfect if you want to experience real Umbrian life away from the crowds.

👉 https://www.umbriatourism.it/en/-/bettona

🍷 Late May Events

🏰🍷 Medieval Banquet – Castiglion Fiorentino (May 23, 2026)

Set in the enchanting Cloister of San Francesco, this unique evening brings the magic of the Middle Ages back to life in the heart of Castiglion Fiorentino. Organized by the Terziere di Porta Fiorentina, the event offers an immersive experience where history, food, and entertainment come together. Guests are invited to enjoy a traditional medieval-style dinner, surrounded by candlelight and historic architecture, while jesters, musicians, and performers recreate the lively atmosphere of a bygone era. ✨

🍷 Radda nel Bicchiere (May 23–24, 2026)

In the heart of Chianti, the charming village of Radda in Chianti hosts the 29th edition of Radda nel Bicchiere, one of the most authentic wine events in the region.

Over two days, Viale Matteotti transforms into an open-air tasting route, where more than 30 local producers present over 100 labels of Chianti Classico. It’s a rare opportunity to meet winemakers, discover small productions, and truly understand the character of this iconic wine territory. The program also includes guided tastings, masterclasses, and the special “Radda Vintage” experience, dedicated to older vintages and deeper insights into the evolution of Chianti wines.

👉https://www.raddanelbicchiere.net/

🌸 Perugia Flower Show (May 23–24, 2026)

Set in the elegant surroundings of Villa del Colle del Cardinale near Perugia, the Perugia Flower Show is one of the most charming spring events in Umbria. Beyond the market, the experience includes gardening courses, creative workshops, and demonstrations for both adults and children — all set within one of the region’s most beautiful historic residences.

👉 https://www.perugiaflowershow.com/

🍝 Sagra dei Pici – Celle sul Rigo (May 29–31, 2026)

In the tiny hilltop village of Celle sul Rigo, one of Tuscany’s most authentic food festivals celebrates its long-standing tradition: the Sagra dei Pici.

Held over the last weekend of May, this beloved event is entirely community-driven. In the weeks leading up to it, locals gather to hand-roll pici — the thick, rustic pasta made with just flour and water — keeping alive a culinary ritual passed down through generations.

During the festival, the main square fills with long communal tables, live music, and the irresistible aroma of pici served with aglione or rich meat ragù. It’s not just about food — it’s a true celebration of Tuscan village life, where simplicity, tradition, and community come together in the most genuine way.

👉 http://www.sagradeipici.it/

🍇 Cantine Aperte – Wine Experience Weekend (May 30–31, 2026)

One of the most anticipated events of the year, Cantine Aperte invites you to explore wineries across Tuscany and Umbria. Enjoy tastings, vineyard tours, and unforgettable moments with local producers in the heart of the countryside.

👉 https://www.movimentoturismovino.it/en/cantine-aperte/

🐎 Palio dell’Oca – Orvieto (May 30, 2026)

A fascinating medieval reenactment in the stunning setting of Piazza del Popolo. Knights in costume compete in a historical joust, creating a unique and cinematic atmosphere in one of Umbria’s most beautiful towns.

👉 https://www.orvietoviva.com

🏹 Palio della Balestra – Gubbio (Last Sunday of May 2026)

A historic crossbow competition between Gubbio and Sansepolcro, held in a spectacular medieval setting. This centuries-old tradition is one of the most authentic historical events in the region.

👉 https://www.balestrierigubbio.it

🔥 🍇 The Pastrignocchi Festival  – Cetona (May 30 to June 2 2026)

Set in the charming main square of Cetona, this traditional food festival celebrates the authentic flavors of Tuscan rural cuisine. At its heart are pastrignocchi, a handmade pasta made with simple ingredients, and cuculi, a rustic local specialty—both prepared following recipes passed down through generations.

Over four convivial days, the village comes alive with long communal dinners, live music, and a warm, festive atmosphere where locals and visitors gather to experience true Italian hospitality.

🍇 🍇 🍷🌿 Mostra del Chianti  at Montespertoli – (May 30 to June 7 2026)

This historic 68th edition, festival recreates the atmosphere of old farmyard gatherings, where locals once came together after long days in the fields to share food, wine, music, and stories under the stars. Today, that same spirit lives on through traditional dinners, folk music, dancing, and community celebrations that welcome visitors into the heart of local culture. 🍇✨

🌿 More  Experiences in Tuscany and Umbria in May

May is perfect for outdoor activities.

Some of the best experiences include:

• visit Palazzo delle Papesse in Siena – one of the most impressive in humanistic Siena, is a symbol of the dynastic policy of Enea Silvio Piccolomini, Pope Pius II, who ascended to the papal throne in 1458.
• Horseback riding in the countryside
• Visit Rothko exhibition in Florence at Palazzo Strozzi
• Visiting hilltop villages like Città della Pieve and Montepulciano

This is when Tuscany and Umbria show their most beautiful side.

🍝 Authentic Food Experiences (Our Favorite)

No trip is complete without experiencing local cuisine.

One of the most memorable things to do in Tuscany and Umbria in May is joining a cooking class.

👉 At our farmhouse, you can experience a hands-on class:
https://www.slowcookingschool.com/

You will learn how to make fresh pasta, enjoy a full meal, and connect with real Italian traditions.

🏡 A Perfect Day in Tuscany and Umbria in May

To truly enjoy the region, we always suggest a slow rhythm:

• Morning: cooking class or local market
• Afternoon: relax by the pool or explore the countryside
• Evening: aperitivo in a small village + dinner

This is the essence of Italian slow living.

✨ Why Visit Tuscany and Umbria in May

• Perfect weather (not too hot)
• Fewer crowds than summer
• Nature in full bloom
• Authentic festivals and events

🌿 Plan Your Stay

If you are looking for a place to experience all of this, discover our villas and experiences at Il Fontanaro:

👉 https://www.countryslowliving.com/

We offer:

• Private villas in the countryside
• Cooking classes and experiences
• Tailored recommendations to explore Tuscany and Umbria