From Florence to Chianti: A Scenic Journey through Hills and Vineyards

High-resolution photo of a panoramic road winding through the Chianti hills, surrounded by well-aligned vineyards and rows of cypress trees.

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: 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: First Stop: Greve in Chianti, the Wine Capital What to see: Nearby wineries: 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: 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: Bonus: Panoramic views of Chianti Classico vineyards. Radda in Chianti: Medieval Walls and Elegant Wines What to see: Suggested wineries: Did you know? Radda was once the historical capital of the Chianti League. Castellina in Chianti: Etruscans, Towers, and Wine Shops What to do: 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: For cyclists: Gaiole is the starting point of the famous L’Eroica vintage bike race. Alternative and Romantic Itineraries Photography Trail Romantic Trail Slow Travel Trail When to Go and What to Bring Best time: April to October, with peak beauty in May–June and September–October. Don’t forget: 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: Book now at tuscanyprivatetours.net and enjoy a panoramic journey from Florence to Chianti that you’ll never forget.