Things to Do in Tuscany and Umbria: May 2026
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.
💜 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
🎈 Kite Festival – Lake Trasimeno
One of the most joyful and visual events of spring, the International Kite Festival fills the skies above Lake Trasimeno with colorful kites and hot air balloons. It’s a relaxed, family-friendly event with a magical atmosphere, perfect for a slow afternoon by the lake.
👉 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/
Paciano Open Musiem 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
🍇 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.
🏹 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
🌿 Outdoor Experiences in Tuscany and Umbria in May
May is perfect for outdoor activities.
Some of the best experiences include:
- Cycling through vineyards and olive groves
- Horseback riding in the countryside
- Walking along Lake Trasimeno at sunset
- 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
