“The routes were all excellent, and I particularly liked the day trip from Montepulciano and also the ride from Cortona to Sansepolcro with its beautiful views and incredible downhill section to the flat valley.” – Lisa M, 2024 Tuscany Biking Participant
Tuscany is the classic Italian bike tour location, known for its beautiful roads, open vistas, and charming hilltop towns. The delicious food and wine don’t hurt either!
The curvaceous roads that run from Siena to the Val d’Orcia (a World Heritage site) and from Montepulciano towards Cortona and the Val di Chiana are the main gateway into the heart of Central Italy. No other region of Italy conjures up such classic Italian images: the hamlets and hilltop towns, terracotta rooftops, swaying cypress, and golden valleys. The roads both paved and dirt are pretty much surrounded by silence. Yes …ok … there are hills to climb…but your efforts will be well rewarded by the simply perfect views and beautiful scenery in every season.
In each of the towns you will stay, the locals gather, just like in old times, in the piazza every afternoon for a walk in their “corso” (the old town’s main road) looking for a stroll with friends or a good espresso. This simple way of life is Italy’s best kept secret. Sport and culture can be found on the same roads, which are perfect for cyclists who love to ride in the shadow of ancient civilizations. Here travelling requires frequent stops to take it all in; there are towns and villages that will take your breath away, gelaterias to test, and scenic vistas that will make any photographer look professional.
After a ride through rolling green wheat fields and vineyards, zig-zagging through lines of cypress, you will taste the true flavors of this land – pecorino cheese, fruity olive oils, the famous Tuscan wines, and the warmth of the local’s hospitality each evening.
The cycling takes place on a combination of paved rural roads and dirt roads. Our Italian partner Giovanni’s hybrid bikes are perfect for this riding with easy enough gears to get you to the top of any hill and a strong enough frame to work both on and off the pavement. You can rent an e-bike if you prefer. What’s more, we offer GPS units mounted on our bicycles that will allow you to more easily enjoy the biking without having to read route directions
Note we have plenty of biking options in Italy: see our Puglia Biking and Italy Coast-to-Coast Biking tours for more Private and Self-Guided tour options.
Private Tours
Grab your friends and family and pick a date. A private tour can provide the best of both worlds—you get to go on vacation with your friends and family, you choose your dates, and we take care of the stress and worry of researching and planning all the details of your itinerary. You can book this as a private tour with a minimum of 8 participants (tours with less than 10 will have one Italian-based guide).
Start planning your private tourSelf-Guided Tours
Self-Guided Tour Price: $2,600 for seven days with a minimum of 2 people.
This is a classic Italian bike tour location, lovely for traveling on your own along the beautiful roads, between the charming hilltop towns, taking your time relishing the delicious food and wine. Some hills can be challenging unless you are on an e-bike.
Details
- Cost Per Person: $4,200
- Self-Guided Tour Cost Per Person: $2,600
- Single Supplement: $500
- Private Tour Minimum: 8
- Self Guided Tour Minimum: 2
- Activities: Biking
- Difficulty: Moderate
- Guides: Giovanni Ramaccioni
Other Info: > Bike rental E25 per day.
> E-bike rental E40 per day.
> Private tours with small numbers (less than ten) will have one Italian-based guide.
Trip Highlights
- Bike through iconically beautiful landscapes of rolling hills, olive groves, and waving wheat fields
- Indulge in divine local cuisine (each town has its own signature pasta!) and wines
- See this amazing country the way the locals do – by bike!
- Visit famous hilltop towns such as Siena, Montalcino, and Montepulciano
Day 1
We meet in the heart of Tuscany in the town of Siena. In the 12th century, it was one of Italy’s most powerful city-states, but now the city inspires awe with its medieval architecture, huge central square (el Campo), and protective walls. After introductions among the group and to our bicycles, we make use of our surroundings and do a walking tour of the city, saving the riding for tomorrow. Dinner tonight is in a nearby restaurant in the heart of Siena.
Day 2
After breakfast we begin our ride through rolling hills, forests, and farmlands – much of it along a ridgeline – on our way to the town of Buonconvento. Buonconvento is a valley town with a Roman and pre-Roman Etruscan past. Those interested can do a morning extension to the Abbey of Monte Oliveto Maggiore. After an optional stop for lunch in Buonconvento, we'll continue on the famous wine town of Montalcino where we'll check into our central hotel and have dinner in town.
Biking Distance: 50 KM with an optional extension
Day 3
Today we ride to Montepulciano, famed for its medieval walking streets. We cycle along back roads with views of quintessential Tuscan valleys and stop at an abbey, several small towns and a centuries-old monastery: the perfectly preserved red brick Sant’Anna in Camprena, where some of the beautiful scenes for the movie The English Patient were shot. In Montepulciano we'll do a tasting in an ancient subterranean wine cave of the famed Vino Nobile red wines. You'll also have time to walk the streets for shopping or sightseeing before we gather for dinner.
Biking Distance: 40 KM or optional 70 KM long route
Day 3
Today we have a loop ride so you don't need to pack up after breakfast. Instead, we'll do a loop cycling ride. Our route will take us to the cute village of Monticchiello, which has a gelato shop overlooking the valley below that offers the best view of any we’ve ever visited! From there you can choose a route through Bagno Vignoni, a natural hot springs/bath with ancient Roman ruins. We then reach Pienza, an amazing hilltop town with a view over the entire Val d’Orcia below, one of the most famed valleys of Tuscany. You can stroll on the fantastic rampart overlooking the valley and wander through the town’s historic streets. Our loop continues back to Montepulciano, where our Italian guide will offer his knowledge about the role Montepulciano played in Tuscan history on a walking tour of the city. This evening, we enjoy dinner at a local trattoria and an optional Limoncello (the classic Italian after-dinner drink) at a local taverna.
Biking Distance: 40 or 60 KM
Day 5
Today we leave the Val di Chiana area first east and then north to the small city of Cortona. Our initial ride is downhill from the heights of Montepulciano and then it is relatively flat (or perhaps undulating) across the valley floor. We cycle on the shores of big Lake Trasimeno and then turn north towards Cortona. Also perched on a hill, Cortona has a beautiful location but this means it will be uphill for our final kilometers. Known as the setting for the book and movie Under the Tuscan Sun, Cortona is an amazing city to talk around. We'll have time for an afternoon tasting of locally-made chocolates at a small private chocolatier before eating another delicious Italian meal.
Biking Distance: 40 KM
DAY 6
Today we head further north to the very edge of Tuscany. Our route takes us even higher from Cortona, up and over a pass at Portole with amazing views of what seems like all of Tuscany below. Then it is down, down, down as a reward for your efforts before we come to the flat Tiber Valley below. Our riding stays flat but we'll be hemmed in by the nearby Apennine mountain chain. Our destination is the town of Sansepolcro, which is less touristed but just as amazing as the famous towns we have visited so far - which makes it perhaps our favorite. In town you'll want to wander the main corso as the day ends; it seems like everyone who lives here is out strolling, drinking, talking, and laughing. Dinner tonight is in town.
Biking Distance: 70 KM
Day 7
After breakfast, you can take a final loop ride on the flat plain north of the city. Then it is time to shower and check out. You can take a train from Sansepolcro to the main cities of Milan, Florence, or Rome to continue your onward travels.
Biking Distance: 20 KM
Trip Accommodations
NIGHT 1 >> HOTEL CHIUSARELLI / SIENA
Located in an 1870 neo-classical villa, this three-star hotel is perfectly located in the heart of Siena, ideal for walking around this lovely city.
NIGHT 2 >> ALBERGO IL GIGLIO / MONTALCINO
This hotel has been open since the late 1800s when it was used as a coachhouse. The three-star, family-run hotel is located right on the main walking street in town.
NIGHTS 3 & 4 >> B&B L’AGNOLO / MONTEPULCIANO
This three-star property is located on the ground floor of an ancient palace located in the heart of Montepulciano.
NIGHT 5 >> HOTEL SAN MICHELE / CORTONA
The San Michele is not only in the heart of the city but it is the closest hotel to Cortona's main sites, including the lovely piazza. You will love the four-star luxury, including an option to enjoy the spa.
NIGHT 6 >> LOCANDA IL GIGLIO / SANSEPOLCRO
The second il Giglio of our trip is a small, unassuming hotel in the center of Sansepolcro. Run by our friend Alessia who we have known for decades, since her father Alessio was the proprietor.
Book this TourArrival & Departure
Zephyr guides meet you in the town of Siena in central Tuscany the morning of the first day of the tour. On the last day of the tour, we will transport you to the Sansepolcro train station before noon, where you can return to Rome or Florence. We highly recommend arriving at least a day early and also extending your vacation in Italy if possible! We will provide more specific travel information upon your booking.
What's Included
- Two Zephyr guides accompany each trip, with a third added as necessary.
- Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
- All of your dinners except one, and all breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches and one dinner open so that you have time to explore and enjoy the local flavors en route.
- All your transportation is included once you meet your guides on the first day.
- All group activities are included.
- NOT INCLUDED Beverages, desserts, lunches, one dinner, gratuities to your guides, personal expenses and travel to and from the destination.
Weather
We like visiting Tuscany and Umbria during the shoulder season months. The average high temperature in Tuscany and Umbria in May is a moderate 69 degrees Fahrenheit while in September it is about five degrees warmer. Evenings are nice, with low temperatures of an average 53 and 60 degrees for the two months. It averages only 7 days of rain in either month, so while we might get a few showers our chances are excellent for good weather. However, Tuscany can be beautiful any time between April and October, although you might need to deal with hot days in the summer months.
Extending Your Vacation
Wow. Italy has so many things to do it is hard to choose. If you are interested in ancient monuments, visit Rome for sure. If you are interested in art, stay after the tour in Florence and see Michelangelo’s David sculpture. If you want to do a little more hiking, head north to the Dolomites.
Wine & Food
As everyone knows, Italy has outstanding wine and food. Just being there, taking in the incredible meals accompanied by delicious local wines, is fantastic. We augment this by providing specific food and wine experiences, including a visit to a sheep cheese farm, a tour of a traditional olive oil mill, a cooking class, and several wine tastings. You definitely don’t need to be a wine or food expert to enjoy this tour. In fact, you don’t even need any specific knowledge at all. All you need is an open mind, an ability to discern what you like and don’t like, and an adventurous spirit.
Bicycling
Each biking day we have two or three different route options with an average of about 35, 50, and 70 kilometers (or 22, 31, or 44 miles). Our goal is to have short options every biker can complete and long options that will tire out even avid cyclists. We have found in the past that non-cyclists who join us in Italy will do just fine and avid cyclists will find our longer hill routes absolutely amazing.
Pedals & Seats
You can bring your own pedals, shoes, and bike seat if you wish to “personalize” your bike with what you are used to at home. You also have the option to rent an e-bike where you pedal normally but use a battery engine for extra power up hills.
Type of Person Who Would Enjoy This Trip
Wine lovers! Pasta lovers! Actually, we can recommend this trip for almost everyone. If you are a serious adventurer, we have plenty of distance for you. If you prefer hanging out in towns and sampling the wines, we have more than enough of that to satisfy. If you are into food and wine, we think our active Food & Wine tours are the best.
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