TUSCANY · ITALY
Hill towns, vineyards, Renaissance afternoons.
Wine days, cooking afternoons, balloon flights and slow drives through cypress country. Florence, Siena, San Gimignano, Pisa, Lucca and the Chianti hills in between.
Only in Tuscany
A wine, a skyline and a sunrise the rest of Italy can’t match.
Plenty of Italian regions grow grapes, keep medieval towers and run balloon flights. None lay them on together like this. The Sangiovese is grown where the name is protected. The towers stand where they were built in the 1200s. The balloon basket lifts off over the same Val d’Orcia hills you’ll recognise from every postcard.
In the cellars
Chianti, Where Chianti Is Made
Sangiovese turns into Chianti Classico on a strip of hills the EU has fenced off with a legal boundary. Cross that boundary and the wine is something else. The black-rooster cellars between Greve, Radda and Castellina are the only place on earth where the wine, the soil and the name align.
- 1 Florence: Pisa, Siena, San Gimignano, and Chianti Experience
- 2 Florence: Chianti Wineries Tour with Wine Tasting
- 3 Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch
On the skyline
The Medieval Skyscrapers
San Gimignano kept fourteen of its medieval tower-houses standing — built tall in the 1200s as a status symbol and never demolished. Walk into the centre and the skyline reads more like a tiny Manhattan than a Tuscan hill town. The Vernaccia served in the piazzas grew on these slopes long before the towers.
- 1 Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- 2 From Florence: Siena, San Gimignano, Pisa & Lunch at Winery
- 3 From Florence: San Gimignano, Siena, and Chianti Wine Tour
From above
Sunrise Over Val d’Orcia
A few thousand feet above the cypress avenues, the geometry that fills every Tuscan postcard makes sense — the spiralled vineyard rows, the lone hilltop farmhouses, the river bends. The Val d’Orcia and Chianti basins are the only place flights take off into this exact landscape.
- 1 Florence: Balloon Flight Over Tuscany
- 2 Experience the Magic of Tuscany from a Hot Air Balloon
- 3 Hot Air Balloon ride in Tuscany countryside from Chianti
The first day in Tuscany
If you can only book one tour, book this one.
More travellers leave Florence on this single tour than any other we cover. A long day picking up the canon — vineyards, hill towns and a Tuscan lunch — without a rental car to deal with.
The classics
Tuscany’s Most Popular Tours
Chianti vineyards, Florence galleries, San Gimignano towers, Tuscan farmhouse lunches. The reason most travellers fly into Florence.
By town
Pick a town.
Each town is its own day. Florence for the galleries. Chianti for the vineyards. Siena for the medieval piazza. San Gimignano for the towers. Montepulciano for the Vino Nobile.
By experience
Or pick how you want to spend the day.
Wine tasting if you want a cellar. Cooking class if you want to take the food home. Vespa or vintage Fiat if you want the postcard ride. Hot air balloon if you want the postcard view. A long lunch if you just want to slow down.
The Tuscan wine triangle
Three DOCGs. One region.
Three of Italy’s most-protected wine names sit inside a triangle you can drive in a long afternoon — and they don’t coexist anywhere else. Same grape, three soils, three towns. Pick the cellar door that fits your day.
Inside the cellars
Where the host pours it themselves.
Family wineries with the cellar door open and the winemaker at the table. If you only have time for three tastings, start with these.
Out of the city
Day trips that leave Florence at sunrise.
Pisa, Siena, San Gimignano and a winery lunch — the days that pack a week of Tuscany into one. Our three favourites for the early starts.
At the table
Cook with a Tuscan family.
Pasta from scratch, gelato, a long lunch in a farmhouse kitchen. Three classes you can book without speaking a word of Italian, and the host pours the wine.
The Italian way to see the hills
By Vespa, vintage Fiat or pedal.
Italian engineering, Tuscan geography. Three options for the day you want the cypresses on either side and the road in front of you.
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