Luxury Villas Tuscany and Mansions for Rent

Florence & big‑ticket culture

• Maggio Musicale Fiorentino – 19 Apr – 1 Jul 2026. Florence’s renowned opera and symphonic festival celebrates its 88th edition with a springtime programme spanning April to July. May highlights include Dvořák’s “New World” symphony on 3 May and Verdi’s opera Un Ballo in Maschera staged 12–24 May other concerts feature works by Mahler, Rimsky‑Korsakov and Beethoven. Performances take place at Teatro del Maggio near the Cascine park.

• International Handicraft Exhibition (MIDA) – 25 Apr – 3 May 2026. Now in its 90th edition, this historic fair at Florence’s Fortezza da Basso showcases Italian and international craftsmanship, with workshops, live demonstrations, cooking shows and tastings. It’s a great way to see artisans at work and buy unique souvenirs.

Renaissance fairs, music & boutique events

• Pontassieve Renaissance Fair (Festa Rinascimentale) – 7–10 May 2026. The town of Pontassieve, east of Florence, transforms into a Renaissance village with a historical parade, “vintage” markets, birds‑of‑prey shows, archery demonstrations and reenacted games. Opening hours are 19:00–23:00 on 7–8 May and 09:00–23:00 on 9–10 May; admission is free.

• Flash Festival – 13–16 May 2026. A four‑day boutique festival in Castiglion Fiorentino combining live music, communal dining, yoga and wine tastings (official site headline: “Flash Festival – 13–16 May 2026”). Expect an intimate gathering of international acts and Tuscan culinary experiences amid olive groves and vineyards.

• Maggio Castiglionese – throughout May. Castiglion Fiorentino’s month‑long festival features art exhibitions, trade and agri‑food fairs, and celebrations for the town’s patron saint, San Michele, on 8 May. A new “Primi di Maggio” food festival and the Valdichiana Wine Festival (2–3 May 2026) are part of the programme

Wine & food festivals

• Valdichiana Wine Festival – 2–3 May 2026. Held in Castiglion Fiorentino, this festival offers tastings of wines from across the Valdichiana valley. Combine it with the Maggio Castiglionese events.

• Cantine Aperte (Open Cellars) – 30–31 May 2026. Italy’s biggest wine‑tourism event sees wineries across Tuscany open their doors for guided tours and tastings. The movement’s website notes that about 1,000 wineries nationwide participate, offering springtime visits and food pairings.

• Lari Cherry Festival – late May–early June. The hill town of Lari celebrates its Protected Geographical Indication (PGI) cherries with an exhibition‑market, food stands, music and the coveted “Golden Cherry” prize for the best grower. Plan to taste cherry‑based desserts and liqueurs.

• Terricciola Strawberry Festival (Festival della Fragola) – two weekends in May. This festival transforms Terricciola into a strawberry lovers’ paradise with food stalls, concerts, tastings and exhibitions. It’s a family‑friendly event in the Pisan hills.

Floral & folk traditions

• Maggiolata Lucignanese – last two Sundays of May (24 & 31 May 2026). Lucignano’s four districts create elaborate floats covered in fresh flowers and parade through town accompanied by marching bands; the best float wins the Golden Gryphon. Expect a riot of colour and a charming competition atmosphere.

• Barberino in Fiore – first weekend of May (dates tbc). Barberino Val d’Elsa hosts a flower market with rose and plant displays, local wine and food tastings, concerts and craft stalls. An earlier edition (2022) offered jazz concerts, guided tours and visits to historic cellars; similar programming is expected in 2026.

Special fairs & medieval reenactments

• Renaissance fair at Pontassieve (see above). Along with the May fair, many Tuscan towns hold Medieval and Renaissance festivals in spring. Check local calendars for smaller events such as Ferrara’s Palio (in Emilia‑Romagna) or the “Cavalieri di Santa Toscana” tournaments.

May is one of Tuscany’s most festive months—blend these events with vineyard visits and spring blooms for a memorable trip.