Day One — 10-20 km (easy; 1.6 km = 1 mile)

We’ll meet you early afternoon at the train station in Chiusi and shuttle you to our first night’s lodging, San Gregorio Residence, the starting point of your unforgettable adventure. Once you’re settled in your rooms, you’ll have your bicycle adjusted and then you’re off for a short warm up ride. Pienza was believed to be the perfect Renaissance city when it was created in 1459 so we have decided to stay here for the first two nights of your tour.

Day Two — 70 km (easy to moderate)

You will start the day with a wonderful downhill ride through amazing countryside en route to Radicofani, which dates back 1,000 years. It houses one of the most impressive fortresses in all of Tuscany. After a stroll around this hilltop town, it is back on the bikes to cycle by cypress-lined roadways with a stop at a pecorino cheese factory for a tour and light lunch. After the tour, you will finish the day with a climb back up to Pienza.

Day Three — 46 km (moderate to sometimes challenging)

Today's bike ride takes us from Pienza to Monalcino, via Bagno Vignoni, Castiglion d'Orcia and Sant' Antimo, where mass is still said in Gregorian Chant. The abbey is one of the most precious remains of Romanesque architecture in Italy. According to legend Sant' Antimo was founded by Charlemagne at the end of the 8th century. After visiting the abbey, and afterwards enjoying a light lunch, it is off to Montalcino through a sea of vineyards where the Sangiovese grapes are grown for the famous Brunello di Montalcino red wine. We will have a chance to taste Brunellos at the vineyard Le Ragnsie before dinner.

Day Four — 60 km (moderate)

We leave Montalcino en route to Siena, via Buonconvento, Monte Oliveto abbey, Asciano and Le Crete area. The Monte Oliveto Maggiore is still a functioning monastery founded in 1313 by Bernardo Tolomei, a famous professor of law who later devoted his life to God at the age of 40. Afterwards, we continue to the town of Asciano down main street past a number of churches before finishing the day in the Gothic city of Siena.

Day Five — (Day off in Siena)

Today you are on your own to explore Siena, a charming city distinguished by it's medieval architecture. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall and Torre del Mangio — a slender 14th century tower with sweeping views from distinctive white crown. Today will be a day not soon forgotten.

Day Six — 50 km (moderate)

From Siena, your ride today will take you through the Chianti red wine countryside to Castellina via San Felice, Castello di Brolio and Radda following the Via Chiantigiana. To this day, Castellina is still a very active village with locals and tourists mingling in the small narrow streets. Before dinner you will enjoy another wine tasting at Casa Emma where varieties such as Merlot are grown but the fields are mostly covered with Sangiovese grape.

Day Seven — 58 km (moderate to sometimes challenging) 

Leaving Castellina you will cycle past Monteriggioni, literally a town in a castle, as you make your way to San Gimignano. The castle is barely 200 meters across and its 80 residents all reside within the picture-perfect round turreted walls. More vineyards await us today but you will be amazed at how different they look once you get in to the district of San Gimignano. Also known as the City of Towers, it was founded around the 8th century and at one time home to more than 15,000 people. After visiting the town, we will cycle the last few kms to our agritourismo.

Day Eight — Farewell

Today is our last chance to savour the scenery together before departing. We're always sad to part, but we know the friendships we make in Tuscany will continue to enrich our lives in the years ahead!

* Details subject to change.