Beyond Florence lies the Tuscan countryside — arguably the most beautiful landscape in Europe. Rolling hills covered in cypress trees, medieval hilltop towns, vineyards stretching to the horizon, and a quality of life that has attracted visitors since the time of the Etruscans. Siena, San Gimignano, the Chianti wine region, and the Val d'Orcia valley offer the essence of the Italian dream.
Siena — The Perfect Medieval City
Siena is Florence's great rival — frozen in its medieval Gothic splendour. The shell-shaped Piazza del Campo is perhaps Italy's most beautiful square, where the famous Palio horse race thunders twice a year (July 2 and August 16). The magnificent black-and-white Duomo is filled with works by Donatello, Michelangelo, and Bernini. And the city's 17 contrade (districts) still maintain fierce neighbourhood rivalries dating back centuries.
Getting there: Bus from Florence (1.5 hours, €8) — the bus drops you right at the centre. Driving through Chianti is the scenic alternative.
San Gimignano — Manhattan of the Middle Ages
This tiny hilltop town is famous for its 14 medieval towers (originally 72!) that give it an astonishing skyline visible from kilometres away. Walking through the town walls, you enter a perfectly preserved 13th-century world. Don't miss the Vernaccia di San Gimignano white wine and the world-champion gelato at Gelateria Dondoli on the main square.
Chianti Wine Country
The rolling hills between Florence and Siena produce Italy's most famous red wine — Chianti Classico, marked by the black rooster (Gallo Nero) label. Drive (or cycle!) through villages like Greve in Chianti, Castellina, and Radda, stopping at estates for tastings. The landscape of vines, olive groves, and stone farmhouses is the Tuscany of postcards and dreams.
Val d'Orcia — UNESCO Landscape
The Val d'Orcia valley south of Siena is a UNESCO World Heritage cultural landscape — and the most photographed countryside in Italy. The lone cypress on a hilltop, the clay hills of the Crete Senesi, the Renaissance perfection of Pienza (the "ideal city" built by a Pope), and the thermal baths of Bagno Vignoni where steaming water fills the central piazza.
Practical Tips
- Best way to explore: Rent a car — Tuscan roads are beautiful and distances are short
- Wine tours: From €80-150 per person including tastings, lunch, and transport from Florence
- Food: Pici pasta with wild boar ragù, ribollita (bread soup), pecorino cheese from Pienza, cantuccini biscuits with Vin Santo
- Best time: May-June (wildflowers) or September-October (harvest, warm light)
Bring Tuscany Home
The medieval towers, the cypress-lined roads, the rolling vineyards — Tuscany is the landscape of the Italian soul. Our MemBoards souvenir cutting boards capture the golden beauty of Italy's heartland.