Fiesole, Chianti & Siena

Fiesole is only 8 km northeast of Florence on a hill overlooking the city — yet it feels like a different world. The Etruscan foundation (7th century BC) is older than Florence itself and was once the more powerful city. Today, Fiesole is a retreat of tranquility: a village square with a Romanesque cathedral, a Roman amphitheater, and a panoramic view that stretches to the Apuan Alps on clear days.

Sights

• Teatro Romano: The Roman amphitheater (1st century BC) is remarkably well-preserved and used in summer for concerts and theater (Estate Fiesolana, June–August). The acoustics are fantastic. In the adjacent archaeological park: Etruscan temples, Roman baths, and a small museum. Admission: 7€.
• Cathedral of Fiesole: The Romanesque Cattedrale di San Romolo (1028) with its distinctive bell tower dominates the main square. Simple and atmospheric.
• Monastery of San Francesco: At the top of the hill, above the square — a Franciscan monastery from the 14th century with a tiny cloister and the best viewpoint over Florence. The ascent through the forest is meditative and wonderfully cool in summer.

Getting There & Tips

Bus 7 from Piazza San Marco in Florence — 20 minutes, every 15–20 minutes, 1.50€. The ride through the villa-lined hills is an experience in itself. Plan: Go in the morning, visit the amphitheater, have lunch on Piazza Mino (Trattoria la Reggia degli Etruschi has a balcony with panoramic views), stroll to the Monastery of San Francesco in the afternoon, return to Florence for an aperitivo.

The Chianti is what most people envision when they say "Tuscany": gentle hills with cypress-lined avenues, medieval villages on hilltops, wineries with views, and endless olive groves. The region between Florence and Siena is the heart of the Chianti Classico DOCG — one of the most famous wine-growing areas in the world.

Wine & Wineries

The Chianti Classico is mainly made from the Sangiovese grape — recognizable by the black rooster (Gallo Nero) on the bottle. The region's wine production ranges from rustic everyday wines to internationally award-winning Riservas. The best wineries offer tastings and tours — often with views of the most beautiful landscape in the world:

• Castello di Brolio: The oldest winery in Chianti (since 1141), birthplace of the modern Chianti Classico. Baron Bettino Ricasoli defined the formula here. Tour + tasting: from 25€.
• Antinori nel Chianti Classico: The futuristic winery of the legendary Antinori family (since 1385!) in an architectural masterpiece that blends into the hills. Restaurant, wine bar, tasting. From 25€.
• Castello di Ama: Wine and contemporary art — installations by international artists are scattered among the vines on the estate. Excellent wines and an unforgettable experience.

The Most Beautiful Villages

• Greve in Chianti: The "Gateway to Chianti" with a triangular marketplace (Piazza Matteotti), a famous butcher shop (Macelleria Falorni), and a wine museum. Saturdays: weekly market.
• Castellina in Chianti: Medieval fortress on a ridge, underground passages (Via delle Volte), and wine bars with panoramic views.
• Radda in Chianti: Perhaps the most beautiful Chianti village — a labyrinth of medieval alleys on a ridge, with excellent restaurants and wineries within walking distance.

Getting There & Organization

Chianti is difficult to explore without a car — public transport is sporadic. The best options: rental car (from 35€/day), organized wine tour from Florence (from 60€ per person, half-day; from 90€ full day with lunch) or bike tour (sporty but delightful — e-bikes recommended). Travel time from Florence: 30–60 minutes depending on the destination.

Siena

Siena is Florence's eternal rival — and in some ways even more beautiful. The Gothic old town (UNESCO World Heritage Site) has hardly changed since the 14th century: The shell-shaped Piazza del Campo is one of the most spectacular squares in the world, the cathedral (Duomo di Siena) a masterpiece of black and white marble, and the alleys exude a timelessness that Florence has lost.

• Piazza del Campo: The sloping, shell-shaped square is the heart of Siena — here, twice a year (July 2 and August 16), the Palio di Siena takes place, the wildest horse race in the world. The 17 Contrade (districts) compete against each other — a spectacle of passion, rivalry, and medieval pomp.
• Cathedral of Siena: The Romanesque-Gothic cathedral with its black and white striped facade and unique marble floor (56 scenes, fully revealed only in September/October) is breathtaking. Also: Piccolomini Library with frescoes by Pinturicchio, glowing in colors as if painted yesterday.
• Museo Civico in Palazzo Pubblico: Ambrogio Lorenzetti's "Allegory of Good and Bad Government" (1338–1339) — the most famous political painting of the Middle Ages.

Getting there: Bus (SITA/Tiemme) from Florence bus station (near Santa Maria Novella station), 75 minutes, from 8€. Or train: Florence–Siena, about 90 minutes, from 10€ (station is below the old town, 10 min. walk or escalator).

San Gimignano

San Gimignano — the "City of Towers" — is quintessential postcard Tuscany: 14 medieval family towers rise like skyscrapers from the 13th century into the Tuscan sky. In the Middle Ages, there were 72 towers — each noble family built higher than the other as a sign of power and wealth.

• Torre Grossa: The only climbable tower (54 meters, 200 steps). From the top: 360° panorama over the Tuscan hills. Admission: 9€.
• Piazza della Cisterna: The triangular main square with the medieval well — also home to Gelateria Dondoli, multiple Gelato World Champion. The flavor "Crema di Santa Fina" (saffron and pine nuts) is legendary.
• Vernaccia di San Gimignano: The local white wine is one of Italy's oldest DOC wines — dry, mineral, and perfect with Tuscan food.

Getting there: Bus from Florence with a transfer in Poggibonsi, about 90 minutes total. Or rental car (50 min. direct). Day tip: San Gimignano + Siena in one day (by car or tour) — morning in San Gimignano, afternoon in Siena.