Tuscany Wine + Bike Tour Itinerary


7 Days  |  6 Nights

Start: Fiesole|  Finish: Florence - Santa Maria Novella Train Station


Pre-Departure | Sunday

We invite you to an intimate dinner and wine tasting with our friends and owners of a small winery in Fiesole, the lovely hill town just 15 minutes drive from Florence. Spend the evening getting to know your fellow Tuscan travelers, while eating a delicious homemade meal and drinking exceptional organic wines.

Day One | Monday – Ready, Set, TUSCANY!

We meet at a historic villa in Fiesole. While sipping on a cappuccino and enjoying the breathtaking views of Florence below, your bags will be loaded into our comfortable shuttle bus. From there, we head straight to Panzano in the Chianti Classico region of Tuscany and our home for the next three nights. We will have our bike fitting and meet our local bike guides. A lovely 15km ride passing vineyards and cypress lined roads will bring us to the charming hamlet of Volpaia where we will have an al fresco lunch. We’ll then hop on our bikes again and take off for Radda-in-Chianti, where we will have a wine tasting at a special Chianti Classico winery. Our shuttle will take us back to our Tuscan farmhouse for a sumptuous dinner paired with the estate’s line of incredible wines.

Total Miles: 15 | Elevation: 1000 feet

Day Two | Tuesday – Castles + Chianti

After a leisurely breakfast, we’ll shuttle over to Gaiole and bike from there to Brolio Castle—the birthplace of Chianti wine. We’ll take a private tour of the stunning estate, concluding with a wine tasting, then bike to an idyllic spot for a picnic lunch. After having our fill of food and photographic moments, we’ll get back our bikes to Castelnuovo to explore another stunning Tuscan castle. Our bus will bring us back to our farmhouse for a little needed R&R. Dinner tonight will be down the road at a famous butcher’s restaurant. Prepare yourselves!

Total Miles: 20 Miles | Elevation: 530 feet

Day Three | Wednesday - Panormas + Pasta

Today, we’ll take off directly from Panzano, biking up and down the rolling hills toward Monte San Micheli. After taking in the panorma of panoramas, we’ll descend down toward Lamole, passing vineyards and oak forests until we reach our traditional trattoria for lunch.  Those who want to continue biking will be taken on a nice long ride back to Panzano. Otherwise, our bus will bring us back to the farmhouse where we can relax and then get our hands dirty with a cooking lesson from a local culinary star. Dinner will be the pasta of our labor.

Total Miles: 20 | Elevation: 1120 feet

Day Four | Thursday -  Fountains + Thermal Springs

Today is all about taking it easy. Mid-morning, our bus will pick us up and bring us to the medieval city of Siena. We’ll have a private city tour, touching upon several important historic buildings as well as their fountain system, which was incredibly advanced for the time. Your local guides will provide you with suggestions for lunch and shopping on your own. In the afternoon, we’ll depart for our next home base: a charming , boutique hotel in the idyllic hamlet of Bagno Vignoni (Population 50!). You will have time to take a dip in the thermal springs before a delicious dinner in town.

Day Five | Friday – Vast Val d’Orcia

Today we get to stretch out across the vast Valley of Orcia, a UNESCO World Cultural Landscape and the setting for various bucolic scenes from the film The Gladiator. Our loop will take us to lunch in Pienza, created in the 15th Century as an ideal expression of Renaissance urbanism, then back to Bagno Vignoni. Enjoy the thermal springs or explore the various walking paths that lead from the city. Dinner will be at another one of the town’s fantastic osterie.

Total Miles: 18 miles | Elevation: 510 feet

Day Six | Saturday – Monks + Montalcino

This morning, we’ll ride to Sant’Antimo, a stunning monastery dating back to the early 12th Century. We’ll have some time to explore the interior and environs and then bike over to a winery with a special relationship to cyclists (you’ll see why!).  Afterward, we’ll bike over to a small, family-run winery that makes incredible wines, including Brunello, one of Italy’s most important red wines. We’ll shuttle back to our boutique hotel to rest and change. Our last supper will be at a gourmet restaurant in Montalcino, where we will toast our wonderful week together!

Total Miles: 24 miles | Elevation: 530 feet

Day Seven | Sunday – A Fond Farewell

Sleep in, take a final dip in the thermal baths, write postcards over the delectable breakfast spread, or stroll around the town this leisurely morning. Our bus will pick us up at noon to bring us back to Florence., dropping us off at the Santa Maria Novella Train Station.