Bespoke Tuscany · Florence or Chianti
A private driver-guide picks you up at your hotel and takes just your group to two small Chianti Classico estates, with a walk in Greve and a home-cooked lunch at the second. Pick it for the pace and the people you meet; book it only if your dates are fixed, because it's non-refundable.
Read this first: the booking is non-refundable. The listing says it can't be cancelled or changed for any reason, and you won't get the money back. Every other tour on this site has free cancellation up to 24 hours before. Buy travel insurance or wait until your dates are certain.
Now the good part. Your driver collects you at your hotel lobby and the day is yours. The listing's itinerary is an hour at Ottomani, a small organic winery at Strada in Chianti in the Greve commune, half an hour in Greve itself, then two hours at Fattoria di Luiano near Mercatale Val di Pesa for a tour, tasting and lunch. All three lie inside the Chianti Classico zone. Guides adapt the route: reviews mention Castellina, other family estates and a third winery on some days. One guest counted more than eight wines.
The price is from $487 per person and moves with group size, so a family of four pays a different rate per head than a couple. For two people that's close to $1,000, about four times the semi-private van day. You get a flexible guide, small producers and a lunch that one guest called "magical". A 2024 reviewer found the first owner more polite than passionate, which happens with family estates.
Your driver meets you in the hotel lobby.
A small organic winery: vineyard, cellar and a first tasting.
A walk around the arcaded square.
Cellar tour, tasting and a long lunch with the estate's wines.
About five hours after pickup, or a drop where you ask.
★★★★★We tasted over 8 different wines all from the region and sampled different olive oil / balsamic from the area. We learned a lot about the wine making process and what makes Chianti / Chianti Classico.
★★★★★He brought us to two adorable family owned wineries and one medium-sized winery in a quaint village. The lunch we had at the last winery was nothing short of magical- home-cooked, delicious food and the views were to die for.
★★★★★Our 2 stops, although very different, were both very enjoyable. We enjoyed our time at both vineyards. The wines were delicious and so was our lunch. The only complaint would be that it all went by too quickly - we would loved to stay even longer!
Read next:
No. The listing says the experience is non-refundable and can't be changed for any reason. If you cancel or ask to amend, you lose what you paid.
The listing names Azienda Agricola Ottomani at Strada in Chianti and Fattoria di Luiano near Mercatale Val di Pesa, with a stop in Greve. Guides sometimes swap in other family estates or Castellina.
From $487 per person in 2026, with the rate depending on how many are in your group. Lunch, tastings and private transport are included; tips aren't.
The listing says transport and surfaces are wheelchair accessible. Mention it when you book so the estates can prepare.
Ready to book
Your own driver and guide, two Chianti Classico estates and lunch, with hotel pickup. Non-refundable.
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