Plan a trip
A route through the vines
Pick a country and a style, and we'll sketch a few days through it — real sub-regions in a sensible order, with what to expect at each stop and when to go, drawn from everything already on the site.
Where to
Style preference
Your route
A 5-stop route through Italy
The character of this trip
Follow the grape, and stay for lunch
Italy is a thousand local wines that barely leave their own valleys, so the trip that suits it is built around place rather than prestige: a grape you may never have met, a village that makes one thing extremely well, a table the wine was always meant to sit at. The hills set the pace and the roads are slower than the map promises, so plan fewer stops than you think you can manage.
Route length
Stops
5
Total driving
~184 km
Behind the wheel
3h 20min
Worth setting aside
4–5 days
What to expect
Notable producers
- Tenuta San Guido — The home of Sassicaia, the wine that started the Bolgheri story.
- Tenuta dell'Ornellaia — Ornellaia and the Merlot Masseto; now owned by the Frescobaldi family.
- Le Macchiole — Bolgheri; a small estate admired for Cabernet Franc, in Paleo, and Merlot.
Best time to visit
Come for harvest, in mid-autumn (October), when the cellars are busiest — or earlier, in early summer (June), for a quieter, greener look at the vines.
~57 km · 1h 2min to the next stop
From Bolgheri, the route turns toward San Gimignano. The climate here: mediterranean, tempered by altitude.
What to expect
Notable producers
- Montenidoli — A small, much-admired estate led by Elisabetta Fagiuoli, known for characterful Vernaccia.
- Panizzi — A leading producer, with a Riserva that ages well.
- Teruzzi & Puthod — The Terre di Tufi estate, one of the region's best-known names.
Best time to visit
Come for harvest, in mid-autumn (October), when the cellars are busiest — or earlier, in early summer (June), for a quieter, greener look at the vines.
~30 km · 32 min to the next stop
San Gimignano is Vernaccia di San Gimignano country; Chianti Classico is Sangiovese. The drive between them is a change of grape, and the glass changes with it.
What to expect
Notable producers
- Castello di Brolio (Ricasoli) — One of Italy's oldest estates, tied to Baron Ricasoli's 19th-century blend.
- Castello di Ama — Gaiole; known for single-vineyard wines and its contemporary art collection.
- Fontodi — Panzano; an organic estate with a leading Sangiovese.
Best time to visit
Come for harvest, in mid-autumn (October), when the cellars are busiest — or earlier, in early summer (June), for a quieter, greener look at the vines.
~66 km · 1h 12min to the next stop
The road from Chianti Classico to Brunello di Montalcino swaps galestro (schistous clay) and alberese (limestone) for clay, limestone and sandstone, in a warmer, drier climate, and the wines follow: fuller, denser and long-lived; at least five years' ageing before release
What to expect
Notable producers
- Biondi-Santi — The estate credited with creating Brunello, at Il Greppo.
- Soldera Case Basse — A small, traditional estate with legendary wines.
- Salvioni — A tiny family estate with a cult following.
Best time to visit
Come for harvest, in mid-autumn (October), when the cellars are busiest — or earlier, in early summer (June), for a quieter, greener look at the vines.
~31 km · 34 min to the next stop
Leaving Brunello di Montalcino behind, the road reaches Vino Nobile di Montepulciano — moderate continental, mediterranean-influenced.
What to expect
Notable producers
- Poliziano — A leading Vino Nobile estate, with the Asinone single vineyard.
- Avignonesi — A long-established estate, also known for its Vin Santo.
- Boscarelli — A small family estate with a reputation for structured, age-worthy Vino Nobile.
Best time to visit
Come for harvest, in mid-autumn (October), when the cellars are busiest — or earlier, in early summer (June), for a quieter, greener look at the vines.