Florence to Siena via Chianti Walk

Make your own way to the first hotel in Florence where you can stow your bags before heading out to explore (check in is usually from 3.00pm but earlier may be possible - check with the hotel reception on arrival). We suggest arriving early so you have time to explore this magnificent city. There is much to see and do including the Duomo, the Uffizi Gallery, the statue of David, the San Lorenzo Market and Piazzale Michelangelo for a panoramic view at sunset! A recommended walking route taking in the magnificent squares and illustrious Arno River starts and ends in the Piazza della Signoria and takes about 3.5 hours. If you'd like to spend some time in Florence before your walk (highly recommended) we can assist with pre-tour accommodation - please ask for our rates.

Begin your day with a scenic 25-minute ride on a local city bus, travelling uphill to the hillside village of Settignano, where your walk begins. From the trail, take in sweeping views of Florence spread out below, framed by cypress-lined ridges, olive groves, and elegant Renaissance villas. The path winds through classic Tuscan landscapes as you make your way to the charming hilltop town of Fiesole, a favourite escape since Roman times. Here, you can explore its well-preserved Etruscan walls, Roman amphitheatre, and peaceful Franciscan monastery, all while enjoying a quieter vantage point above the bustle of Florence. Walking: 8 or 16km/5 or 10mi, +347 or 567m/1138 or 1860ft, -224 or 566m/735 or 1860ft Surf/Unsurf 14/86%

After breakfast, a private transfer takes you into the heart of Tuscany’s wine country, arriving in Greve in Chianti—a charming market town known as the capital of the Chianti Classico region. Once checked in to your hotel, stroll over to Le Cantine di Greve, where you’ll have the chance to sample from a selection of more than 50 regional wines, showcasing the rich variety of local vintages. Later, make the most of the afternoon light with a walk through the rolling vineyards and hilltop views that surround the town. Choose from two scenic routes, both offering a peaceful introduction to the landscapes that make this region so iconic. Option A - a scenic circular walk starting from Greve’s charming main square, heading north into the heart of Chianti Classico country. The route winds past Villa Calcinaia, through a landscape dotted with vineyards, stone farmhouses, and historic “aziende agricole” (working farms) where some of the region’s most respected Chianti wines are produced. It’s a peaceful, picturesque walk offering a taste of rural Tuscany just beyond the town’s edge. Walking: 9km/5.6mi, +225m/738ft, -225m/738ft, Surf/Unsurf 41/59% Option B - This beautiful loop walk takes you through a more rugged side of the Chianti landscape. You’ll wind your way through forests, olive groves, and quiet vineyards, passing secluded villas, crumbling farmsteads, and old stone ruins that hint at centuries past. The highlight is reaching the hilltop hamlet of Montefioralle, one of the most scenic villages in Tuscany, where panoramic views stretch across the surrounding countryside. Walking: 10km/6mi, +358/1400, - 355m/1475ft, Surf/Unsurf 45/55%

This circular walk begins and ends in Panzano, taking you through the gently rolling hills that surround the village. As you follow quiet country roads and trails, you'll enjoy the classic Chianti landscape. Along the way, there are opportunities to spot ancient Roman farmsteads and traditional Tuscan stone houses, offering a deeper glimpse into the region’s agricultural and cultural heritage. It’s a peaceful and scenic route that captures the essence of rural Tuscany. Walking: 11.7km/7.3mi, +385m/1270ft, -385m/1270ft, Surf/Unsurf 25/75%

After breakfast, a short transfer brings you to Monte San Michele, the highest point in the Chianti hills. From the small village of Badiaccia, begin your descent through a forested valley shaded by centuries-old chestnut trees. As the landscape opens up, you’ll arrive in Volpaia, a well preserved medieval hamlet nestled among vineyards and stone castles — the perfect place to pause for a glass of local Chianti at a traditional enoteca (wine shop). From here, the walk continues through classic Tuscan countryside to Radda in Chianti, a lively hill town known for its wine heritage and timeless charm. This is a day filled with natural beauty, rich history, and the unmistakable flavors of Tuscany. Walking: 12-14km/7.5-8.75mi, +506m/1670ft , -668m/2200ft, Surf/Unsurf 17/83%

Today is a scenic loop walk through the countryside surrounding Radda in Chianti. Begin your day exploring the cobbled streets and historic walls of Radda’s old town before heading out on quiet country trails that wind through vineyards, olive groves, and forested ridges. Midway through the walk, stop for lunch in the charming hamlet of Vertine, a tiny medieval village that feels untouched by time. In the afternoon, reward your efforts with a tasting at Colle Bereto, a renowned local winery with stunning views and bold Chianti wines. The walk finishes back in Radda — just in time for a relaxed evening. Walking: 17km/10.5mi, +586m/1934ft, -586m/1934ft, Surf/Unsurf 38/62%

After breakfast, a private transfer brings you to the remarkable city of Siena, one of Italy’s best-preserved medieval treasures. Famous for its thrilling Palio horse race, held twice a year in the dramatic Piazza del Campo, Siena is a city where history and architecture come vividly to life. Spend the day exploring its winding cobbled streets, visiting grand medieval palaces, and taking in the stunning Duomo, a Gothic masterpiece filled with intricate marble detail and artwork. Whether you’re enjoying a coffee in a quiet piazza or admiring the city from its historic walls, Siena offers an unforgettable glimpse into Tuscany’s rich cultural past.

The trip concludes after breakfast. We can also assist with booking an extra night in Siena (highly recommended) on request.