Tuscan Tuscan Classics
Chianti, San Gimignano, Montalcino, Montepulciano and truffle hunting: the postcard towns, without the tour-bus crowds.
Private journeys
Take the detour.
Take the detour.
Find the Tuscany behind the postcard.
Private journeys with local guides: ancient forests and hill towns, family tables and old cellars, hot springs and hidden chapels. The Tuscany the people who live here keep for themselves.
- Transport included
- Tastings included
- Lunch on most tours
- Private, 2 to 8 guests
Opening January 2027
Be first on the list.
Join the waitlist and we will write to you first, before 2027 dates open to everyone. No payment, no obligation.
L
Your Guides
A sommelier who knows the vineyard, and a host who knows its people.
Andrea trained as a sommelier with WSET and spent years working the land as an agricultural technician. In the cellar he explains the wine; out in the rows he shows you why it tastes that way.
Lorenzo brings years of experience in the tour business and a clear rule: only real experiences, never staged ones. Warm, easy-going and genuinely kind, he is the one who makes you feel like friends of the family by lunchtime.
🍷 WSET-trained sommelier🌱 Agricultural technician🧭 Years leading tours🤝 Real experiences only
Together, they guide every Tuscan Detour day in person. Meet the founders →
A sommelier as your guide
WSET training and years in the vineyards: wine explained from the soil up, in English.
Private, just your party
No strangers on board: the minivan, the guide and the day are yours alone.
Built around your itinerary
First visit to Chianti, or your fifth trip back, we plan accordingly.
Door-to-door from Florence
We collect you at your hotel or apartment and bring you back at the end of the day.
Where we go
Two ways into Tuscany
From the classic vineyard roads to the valleys locals keep to themselves, each collection is built for a different kind of day.
Featured itineraries
Start planning your day
Every tour is private, just for your party. "From" prices are per person for a group of 8; each card also shows the price per person for two, and every tour page lets you check the price for your exact group.
Half or Full Day
Chianti Hidden Gems
4–8 hours
2 wineries half day, 3 full day
Max 8 guests
The real Chianti: family-run, organic estates where you sit down with the winemaker and share the passion, and the hard work, behind every bottle, over a truly good glass of wine. All of it off the routes every tour bus takes. Two estates on the half day, three on the full day, and always lunch in the cellar: handmade pasta and local produce, often cooked by the winemaker himself.
Details & FAQ
How do we get there?
We collect you at your hotel or apartment in Florence.
Is lunch included?
Yes, on both the half and the full day: lunch is served in the cellar of one of the estates, with handmade pasta and local produce, often cooked by the winemaker himself.
Dietary requirements?
Vegetarian, vegan, gluten-free: just tell us when you book and the estates will adapt.
Can we buy wine?
Of course. Bottles bought at the wineries are extra, and most producers can ship abroad.
Full Day
San Gimignano & Siena
9 hours
Winery lunch included
Max 8 guests
The towers of San Gimignano in the morning, Siena's Piazza del Campo in the afternoon, with a Vernaccia tasting and lunch at a family estate in between.
Details & FAQ
How do we get there?
We collect you at your hotel or apartment in Florence.
Where do we eat?
Yes: lunch is served at the Vernaccia estate, paired with the wines you taste there.
How much walking is involved?
Both towns are explored on foot, with some cobblestones and gentle slopes: comfortable shoes are a must.
What is Vernaccia?
San Gimignano's historic white wine, the first wine in Italy to earn DOC status, in 1966. You will taste it at the estate, straight from the people who make it.
Full Day
Montalcino
8 hours
Lunch included
Max 8 guests
Brunello country. A day among the vineyards south of Siena, tasting Brunello and Rosso di Montalcino at two estates, with lunch at one of them.
Details & FAQ
How do we get there?
We collect you at your hotel or apartment in Florence.
Is lunch included?
Yes, lunch among the vines at one of the two estates, paired with their own wines.
Brunello or Rosso?
Both. Brunello is the long-aged icon; Rosso di Montalcino is its younger, more immediate sibling. Tasting them side by side is half the fun.
Dietary requirements?
Let us know when booking and we will arrange an alternative menu with the estate.
Full Day
Bolgheri
Full day
3 estates of your choice
2–8 guests
The Super Tuscan coast, south of Livorno. Choose three stops among Ornellaia, Guado al Tasso, Tenuta Fratini and Chiappini, with lunch at Enoteca San Guido as an option.
Details & FAQ
Where does the day start?
From your hotel or apartment in Florence: this tour is private, so the vehicle is yours for the whole day.
Can we visit Sassicaia's winery?
Tenuta San Guido, home of Sassicaia, is not normally open to visitors, but you will taste Bolgheri's great reds at the estates you choose.
Can we ship wine home?
Most estates ship abroad, including to the US. Purchases are paid directly to the producer.
Full Day
Nobile di Montepulciano
8 hours
Two Vino Nobile cellars
Max 8 guests
Vino Nobile at the source: two family-run cellars, then an afternoon in the hill village of Montepulciano.
Details & FAQ
How do we get there?
We collect you at your hotel or apartment in Florence.
Which wineries?
Small, family-run estates: we choose the two cellars for your date and tell you which ones when we confirm.
How much walking is involved?
Montepulciano is a hilltop town with steep, cobbled lanes: wear comfortable shoes.
Full Day
Truffle Hunting & Bubbles
8 hours
Lunch & bubbles
Max 8 guests
A real hunt with working Italian dogs in the woods above San Miniato, lunch built around the find, then a tasting at a winery devoted to sparkling wine.
Details & FAQ
How do we get there?
We collect you at your hotel or apartment in Florence.
When is the best season?
White truffle runs from October to December; the rest of the year we hunt black truffle. The experience is available all year round.
What should we wear?
The hunt is in the woods: sturdy shoes and clothes you do not mind getting a little muddy.
Can we take truffles home?
Yes, truffles can be purchased on site; they are not included in the price.
Tours by Theme
What kind of day are you after?
Wine Tours and More
Not into wine? Come anyway.
Almost every group has someone who doesn't drink, or would rather swap a tasting for something else. These days put food, nature and history first. And since we do the driving, nobody in your group has to stay sober behind the wheel.
Chianti Villages
Medieval Montefioralle, Greve's market square, and lunch at an iconic Chianti Classico winery, as much about the villages as the wine.
Saturnia Hot Springs
The Maremma coast and an afternoon in warm, natural thermal waterfalls.
Casentino
Ancient beech forests, medieval abbeys and mountain villages.
Modena: Ferrari & Balsamic
The Ferrari Museum, lunch at a family acetaia among balsamic barrels, then Modena.
From €280 pp, group of 8 · €400 pp for 2Ready to take the detour?
Tell us who is travelling and what you love. We will reply personally with the right day for you.