The Heart of Tuscany 10 Night

This tour is much like our 8 night Tuscany tour, but even better.  Visit all of our 8 night tour locations plus Cortona.  Sip cappuccino in the morning, then sample the finest Chianti in the afternoon, plus savor fine Italian food all day long.  Oh, and pedal along some of the most beautiful and scenic roads in the world.  What better combination for a romantic getaway or family vacation?  This tour offers the best that Tuscany has to offer, and them some. We offer the best Tuscany bike tours.

The photos you see on this page and our other Tuscany itineraries are not random images that we found online. Nearly all of them are taken by our local guides, Bruno Baldini and Suzanna Bottai, while on their own adventures across the region they call home. The widely said natural beauty and romantic scenes of Tuscany are not over-stated. It is all true. Come and discover for yourself!

Day 1:  Florence to Panzano
Our guide, Bruno, will meet you at in the morning at our the bike rental shop in the heart of Florence*.  After he ensures your rental bike is fit properly you will hit the road! You will ride with Bruno, navigating through the busy Florence streets, on the first leg of your tour – a lovely 49km to ride Panzano. Once at the hotel you will have time to explore the town.  Your luggage will be there when you arrive, so enjoy the pool and try the local Chianti before dinner.  Dinner is included tonight.

Day 2: Panzano to San Gimignano
Your day will include a 50km ride to San Gimignano, the city of towers, along small rolling back-roads.  There is a 20km+ add on possible as well.  Settle in for 2 nights at our historic hotel right in the middle of the old town.  Dinner is included tonight.

Day 3:  San Gimignano Rest Day or Volterra Loop
You can take a day off the bike and rest, shop, or take the beautiful 60km loop to Volterra. Volterra is one of the many famous hilltop towns of Tuscany, full of fine shops and a museum. Dinner is on your own tonight.

Day 4:  San Gimignano to Siena
You have 70km of traffic free back-country roads to Siena today.  Siena is the heart of the region and a beautiful small city.  Settle in for 2 nights.  You eat out both nights so enjoy exploring the old city and all the culinary delights Siena can offer.  Our hotel is inside the town gates and perfectly located for easy exploration of Siena and the surrounding areas.

Day 5:  Siena Exploration
This is a day off the bike to fully explore the historic sites and do some gift shopping.  Dinner is again on your own tonight so keep your eyes peeled for the best option.

Day 6:  Siena to Montalcino
We exit Siena the way we came in on small back roads with grand views of the city.  You head South toward another beautiful small historic hilltop town, Montalcino, the home of the famous Brunello wines. It is 60km of rolling roads to Montalcino. You are on your own for dinner, and there are many fine options to select from.

Day 7:  Montalcino to Montalpulciano
You depart Montalcino to start an eventful day.  The direct route is only 40km but you have several options to add hills and mileage. Included in the journey is the town of Pienza, which will be a great stop for lunch and exploration.  Your hotel is a country house about 1 mile out of Montalpulciano and is surrounded by tidy vineyards of the famous Vino Nobile Di Montalpulciano. This beautiful farmhouse has been wonderfully restored by the owners, who are wine exporters and experts.  They are always willing to provide you with special tours and tasting if you desire.  They can also teach you how to cook an authentic Tuscan meal!  Mara is an outstanding chef who will teach you to cook the meal that will end up being your dinner!  We recommend dinner here both nights.  The cooking school is not included in the price – so let us know in advance if you want the option to ensure that it is arranged.

Day 8:  Montalpulciano Exploration
You can walk to Montalpulciano or cycle there and spend the day exploring this gem.  It is your day to discover and enjoy. Dinner is on your own, including the possibility of taking the class at your hotel!

Day 9:  Montalpulciano to Cortona via Castiglione del Lago
Today you head into Umbria to Lake Trasimeno, and visit the lovely village of Castiglione del Lago.  It is perched perched on a promontory, overlooking the lake, and an excellent lunch stop.  Cortona is another gem.  Your hotel is in the heart of the town to allow easy exploration on your last day.
Hotel Villa Marsili  has no restaurant so you get to explore this wonderful village looking for the an ideal dinner spot.  Ask about Il Falconiere – it has a Michelin Star but is in the hills above town.

Day 10:  Cortona Exploration and Monte Petrano
You can either hit the road on your bike or explore the town.  There are some beautiful rides in the area.  The 2009 Giro had a mountain top finish at Monte Petrano, which is not too far from Cortona.

Day 11:  Cortona to Firenze
You depart for Florence by cycling to the Cortona train depot and catching a morning train**.  The Florence train station is within a few blocks of our bike rental shop where the tour ends. Earlier trains are available and it would be possible to catch an evening flight.  Also, we have several recommendations for hotels near the bike shop and at the airport.

To find out more about how our Self Guided Tours operate, what is included, and what is not, click HERE.

* – We have suggestions for hotels near the bike shop for nights prior to and after the tour.  You will need to spend the night before day 1 in Florence to be at the bike shop early enough to complete the Day 1 itinerary.
** – Not included in the tour price.  Please purchase on your own at the station.