A trip from Florence to Chianti is more than a geographical transfer—it’s a complete sensory experience. Along the way, you’ll encounter iconic landscapes of rolling hills, orderly vineyards, stone villages, and cypress-lined roads. This article presents a scenic itinerary of over 2500 words, ideal for anyone looking to explore the authentic essence of Tuscany, step by step and glass by glass.
Florence: The Starting Point of Art and History
Before heading into the countryside, Florence deserves a slow and thoughtful visit. Dedicate half a day to immerse yourself in the heart of the Renaissance.
Recommended stops:
- Cathedral of Santa Maria del Fiore and Brunelleschi’s Dome
- Piazza della Signoria and Palazzo Vecchio
- Uffizi Gallery
- Walk across Ponte Vecchio
- Traditional lunch in the Oltrarno district (La Casalinga, Trattoria Cammillo)
Tip: End the morning with a coffee and a view at the Oblate Library terrace.
Leaving Florence: The SR222, One of Italy’s Most Beautiful Roads
Heading south from Florence, you’ll enter the famous SR222 Chiantigiana Road, considered one of the most beautiful drives in Italy thanks to its breathtaking scenery.
Length: about 70 km from Florence to Siena, but even just to Greve or Castellina is stunning.
Ideal for: car, motorcycle, e-bike, or NCC (private driver) for a relaxed ride.
Panoramic spots:
- Piazzale Michelangelo (perfect farewell photo of Florence)
- Hills of Impruneta and San Casciano in Val di Pesa
- Endless views over the vineyards
First Stop: Greve in Chianti, the Wine Capital
What to see:
- Piazza Matteotti with its arcades and artisan shops
- Wine Museum
- Falorni Butcher shop: perfect for a tasting board and a glass of Chianti Classico
Nearby wineries:
- Castello di Verrazzano (guided tour + tasting)
- Montefioralle Winery (intimate, family-run)
- Il Palagio di Panzano (organic with incredible views)
Fun fact: Greve is the birthplace of explorer Giovanni da Verrazzano.
Montefioralle: A Gem Among the VinesJust minutes from Greve, this medieval village is a concentration of Tuscan charm.
What to do:
- Walk through stone streets
- Capture panoramic photos over the vineyards
- Visit small family-run wineries
Tip: Visit in late afternoon to enjoy golden sunset light.
Panzano in Chianti: Culinary Art and Nature
Famous for: Dario Cecchini, Italy’s most renowned butcher-poet.
Don’t miss:
- Lunch or dinner at Officina della Bistecca or Solociccia
- Walk in the Peace Park and the Conca d’Oro wine area
- Tastings at Fontodi or Le Cinciole
Bonus: Panoramic views of Chianti Classico vineyards.
Radda in Chianti: Medieval Walls and Elegant Wines
What to see:
- Historic center and medieval walls
- Palazzo del Podestà
- Wine tastings at the local Pro Loco
Suggested wineries:
- Castello di Albola
- Volpaia (with its own historic village)
- Istine (refined interpretation of the local terroir)
Did you know? Radda was once the historical capital of the Chianti League.
Castellina in Chianti: Etruscans, Towers, and Wine Shops
What to do:
- Stroll along the Via delle Volte
- Visit the Chianti Archaeological Museum
- Climb the medieval tower for 360° views
- Wine tastings at Rocca delle Macìe or Castello di Fonterutoli
Tip: Ideal spot for a light lunch and wine-related shopping.
Gaiole in Chianti and the Castle of Brolio
Must-visit: The Castle of Brolio, estate of the Ricasoli Barons, with historic gardens and jaw-dropping views.
In Gaiole:
- Walk the charming town center
- Visit boutique wineries like Capannelle or Badia a Coltibuono
For cyclists: Gaiole is the starting point of the famous L’Eroica vintage bike race.
Alternative and Romantic Itineraries
Photography Trail
- Sunrise over Florence from Piazzale Michelangelo
- Golden vineyards at sunset in Panzano
- Backlit cypress trees between Radda and Castellina
Romantic Trail
- Private picnic among the vines
- Dinner at a historic villa with hillside views
- Sunset tasting of selected Chianti labels
Slow Travel Trail
- Ride a Vespa or touring bike
- Long stops in villages to discover local crafts
- Slow tastings and long chats with winemakers
When to Go and What to Bring
Best time: April to October, with peak beauty in May–June and September–October.
Don’t forget:
- Comfortable walking shoes for cobbled streets
- Hat and sunscreen
- Camera or smartphone with good lens
- Layered clothing
Discover Chianti with Tuscany Private Tours
To enjoy this journey to the fullest, rely on someone who knows every turn of the Chiantigiana Road. With Tuscany Private Tours, the private driver and expert guide service led by Maurizio Bellini, you can:
- Enjoy the landscapes without the stress of driving
- Visit authentic, less-touristy wineries
- Build a personalized itinerary just for you
- Stop for the best panoramic views and wine tastings
Book now at tuscanyprivatetours.net and enjoy a panoramic journey from Florence to Chianti that you’ll never forget.
