Vineyard Wedding Venues in Tuscany: 10 Wine Estates for 2026

1. Villa Medicea di Lilliano — eight generations of winemakers, eleven kilometres from Florence

Villa Medicea di Lilliano is an 11th-century estate hidden among the vineyards and olive groves of the Chianti hills, once owned by the Medici and held by the Malenchini family since 1830 — now in its eighth generation, with the family's organic wine and olive oil made on the property. It is also a licensed civil ceremony venue, one of very few in the area authorised to host official weddings on-site, with a private chapel, a Limonaia, a Granary, and terraced gardens for celebrations of 250 or more. For couples who want a true family wine estate with Florence eleven kilometres away.

2. Vignamaggio — Chianti Classico's storybook estate

Halfway between Florence and Siena, Il Borgo di Vignamaggio is a restored 15th-century hamlet at the heart of the historic Vignamaggio wine estate — frescoed chapel, 144-seat theatre, grand ballroom, and 17 suites sleeping 55 guests on-site with another 46 at the estate's nearby inn. The estate-grown Chianti Classico features at every celebration, and the vineyards form what the property rightly calls a natural amphitheatre. Up to 250 guests. For couples who want the complete wine-estate weekend, sleeping arrangements included.

3. Villa di Geggiano — the 1786 time capsule with its own label

Six kilometres from Siena among the vineyards of Chianti Classico, Villa di Geggiano has been home to the Bianchi Bandinelli family since 1527 — nearly five centuries of one family tending the same land and pressing the same grapes. The interiors survive exactly as designed in 1786, the private chapel was built in 1768, there is an historic open-air theatre in the garden, and the estate produces organic wines. Up to 180 guests, licensed for civil ceremonies. For couples who want their wine estate to double as a National Heritage site.

4. Castello Banfi — the castle above Montalcino's vines

In Montalcino, Castello Banfi is a beautifully restored medieval castle towering above mountainous forests and rolling vineyards — built in the Middle Ages as Siena's first line of defence against attacks from the south. Ceremonies for up to 100 guests outdoors, with the castle hall as the elegant indoor plan. For couples who want the drama of battlements over a sea of vines.

5. Villa Le Corti — 230 hectares of Chianti Classico

In San Casciano in Val di Pesa, Villa Le Corti is an estate with a history as rich as its wine — more than 500 years of it, worn in Renaissance architecture and a porticoed inner courtyard made for candlelit dinners under string lights. The villa sits amid 230 hectares of vineyards and olive groves in the heart of the Chianti Classico region. Up to 100 guests. For couples who want scale in the landscape and intimacy at the table.

6. Borgo Castelvecchi — a village asleep among its own vines

First recorded in 1043, Borgo Castelvecchi in Radda in Chianti is an entire medieval village hired outright — with a thousand-year-old wine cellar at its heart and the estate's own Chianti Classico poured at dinner. The 18th-century villa and stone houses sleep up to 100 guests, there is an 18th-century chapel for ceremonies, and the pool looks over the Chianti hills. Up to 100 guests. For multi-day celebrations where the whole guest list wakes up inside the wine estate.

7. Villa Grazianella — Montepulciano, by way of the Archbishop

Once the summer residence of the Archbishop of Montepulciano, Villa Grazianella at Fattoria del Cerro (from €21,400) hosts up to 60 guests with nine rooms and two junior suites at the villa, apartments at the Fontelellera vineyard five kilometres away, and — from May 2026 — eight newly renovated suites bringing on-estate sleeping to 64. Fireworks are permitted, and there is a helipad for the grand entrance. For intimate weddings that want a whole wine estate to themselves.

8. Castello La Leccia — the boutique wine resort

Castello La Leccia at Castellina in Chianti is exactly what it calls itself: a boutique wine resort on a vast organic estate of vineyards and olive groves in the heart of Chianti Classico. Ancient stone walls, panoramic terraces over the iconic countryside, and up to 100 guests for the ceremony. For couples who want the wine estate distilled to its essentials — stone, vines, and view.

9. Borgo Villa Certano — Siena's working farm

Minutes from the centre of Siena, Borgo Villa Certano is an active agricultural business producing Chianti wine and extra virgin olive oil — a neoclassical villa with frescoed halls, a winery, an ancient limestone wine cellar, seven country houses once inhabited by farmhands, and a 13th-century Romanesque church for ceremonies. Up to 100 guests, with indoor music running to the small hours. For couples who want a genuine working estate with Siena's treasures on the doorstep.

10. Villa La Palagina — the estate resort in the Chianti hills

On a hillside between vineyards, olive groves, and woodland 30 kilometres from Florence, Villa La Palagina is a 16th-century villa turned countryside resort on a 110-hectare estate that produces its own Chianti wine and olive oil, served in the restaurant. Around 70 guests sleep across the estate's rooms, apartments, and private dimora; celebrations run to 250 across the rustic limonaia barn, indoor halls, and terraces. For big guest lists that still want the wine made on-site.

How to choose between them

Decide what the wine is for. If the estate's own label on the table is the point, go where production is front and centre — Castelvecchi's thousand-year cellar, Vignamaggio's Chianti Classico at every celebration, Lilliano's and Geggiano's organic estate wines, Certano's working winery minutes from Siena. If the vines are the backdrop rather than the story, Banfi and La Leccia deliver the view with fewer moving parts.

Count beds among the vines. Wine estates reward the multi-day wedding, so match the property to the people staying over: Castelvecchi sleeps 100, Vignamaggio 55 on-site plus 46 nearby, La Palagina around 70, Grazianella up to 64 from May 2026. Lilliano sleeps 44 on the estate with partner properties taking the total to 92.

Book on Tuscany's timeline, not yours. The best estates fill 12 or more months out for May to October dates, and exclusive-use properties are the most exposed — one wedding takes the whole estate off the calendar. Our planning timeline shows what to lock when, our Tuscany cost guide covers what it all costs, and a good local planner can sometimes reach dates that never hit the open market.

Shortlisting wine estates? We confirm availability and pricing directly with venue events teams — within 48 hours, free — request a tailored quote.