Wine route
Strada Chiantigiana SR 222
1 day · 72 km · 5 stops
Florence to Siena
Your cellar, your trips, and the wines you've been tracking are right where you left them.
New here?
Free, always. Education first, we'll never sell you anything you didn't ask to see.
Already have an account?
Enter the email you signed up with and we'll send a link to choose a new password.
Tuscany · Wine routes
4 drives, each one a different Tuscany. Pick by the wine you want at the end of the day.
Every road here has a drivable guide behind it: real stops, the time between each one, the estates you can taste at, and a sheet you can print.
The linkable asset
Hover a road on the map, or pick a row beside it, to see what it is. Tap a road on the map to see what it is.
Wine route
1 day · 72 km · 5 stops
Florence to Siena
Wine route
2 days · 73 km · 7 stops
Sinalunga to San Casciano dei Bagni
Wine route
1 day · 63 km · 4 stops
Bolgheri to Populonia
Wine route
1 day · 30 km · 4 stops
Montalcino to Sant'Angelo in Colle
The decision table
One row per road. If you only read one cell, read the driving character.
Swipe the table sideways for what you taste, the driving character and tasting prices.
| Route | Days | Km | Stops | What you taste | Driving character | Guided | Tastings |
|---|---|---|---|---|---|---|---|
| Strada Chiantigiana SR 222 Florence to Siena | 1 | 72 | 5 | A proper ridge road: second and third gear through the hairpins above Greve, open sweepers on the Castellina stretch, slow coach traffic in July and August. | 12 | from €20 | |
| Strada del Vino Nobile Sinalunga to San Casciano dei Bagni | 2 | 73 | 7 | Open ridge running above the Valdichiana: long sightlines, gentle gradients, and the only slow kilometres are the cypress switchbacks up to each town gate. | 8 | by request | |
| Strada del Vino Costa degli Etruschi Bolgheri to Populonia | 1 | 63 | 4 | Mostly flat and fast between the cypress rows, with quick dual-carriageway hops on the SS1; the only real climbing is the last kilometre up to each hilltop village. | 2 | from €60 | |
| Brunello and Rosso loop Montalcino to Sant'Angelo in Colle | 1 | 30 | 4 | Short, steep and slow: single-lane hill roads in second gear, a white-gravel shortcut if you dare, and more tractors than coaches once you leave the fortress car parks. | 6 | from €25 |
Tastings show the lowest listed estate price on each road. Guided tours match to routes automatically as partners list them.
Route by route
Visit prices are set by the winery and availability should be checked before travelling. Bookings open on the estate page or the provider's site.
Full day, longer with tastings
The 69 km hillside road from Florence to Siena that threads through the heart of Chianti Classico.
Estates on this route
2 days
The signposted Valdichiana Senese trail, from the valley floor at Sinalunga over the Vino Nobile hill at Montepulciano and down to the hot springs at San Casciano dei Bagni.
1-2 days
The Tyrrhenian coast itinerary linking Bolgheri, Castagneto Carducci, Suvereto and Val di Cornia.
Estates on this route
Half a day to a full day
A compact loop around the Montalcino hill, taking in Sant'Antimo, the Val d'Orcia and the producer cellars below the village.
Estates on this route
Beyond the roads
From galestro hills in Chianti Classico to the single Brunello rise of Montalcino and the sea-facing Cabernets of Bolgheri, Tuscany is Italian wine's stage in full Renaissance light.