Italy: Tuscany & Umbria Biking & E-Biking

“One of those flash epiphanies of travel, the realization that worlds you’d love vibrantly exist outside your ignorance of them.” 

Frances Mayes

This bike adventure takes place in the heart of Italy in two fantastic provinces: Tuscany and Umbria. As we pedal, we also eat and drink our way across these most delicious areas of this most delectable country! Incredible pastas, pizza, and bruschetta; spectacular scenery with rolling hills, waving wheat fields, and Cypress trees that line the roads like sentinels; medieval hilltop towns with winding cobblestoned streets and inviting shops; country lanes you share only with your fellow cyclists; and – oh – the vino!

We start our tour by riding through one of Italy’s most renowned regions, Tuscany! The wines are some of Italy’s best – and any Italian will tell you Italian wine is the best. Period. The scenery is spectacular and the historic towns provide the perfect excuse to get off our bikes and do a little shopping or sample the local delicacies. Perhaps most importantly to us, Tuscany’s rural roads make the bicycle the perfect vehicle for exploration.

However, Tuscany is also hilly and will be a challenge for some people to negotiate by bike. We do our best to include flat routes where possible but there is no getting around the hills. That is one reason we combine Tuscany with Umbria. You also have the option of renting an e-bike – which you pedal normally but get a battery assist for extra power up hills!

Umbria is just as beautiful as Tuscany, although less well known. In addition, it boasts the Valle di Umbria, a flat valley that makes for a perfect complement to rolling Tuscany. The short bike routes during our final four days are generally flat with an occasional climb up to a worthy hilltop town. The long routes head off to the valley’s sides for more strenuous cycling.

Including both Tuscany and Umbria provides us with the best of the area and suitable bicycling for all ability levels. 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. 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.Italy is truly an amazing country with much to offer and this seven-day bicycling tour through Tuscany and Umbria offers some of the highlights of the area.

Trip Favorite Moments & Reviews

“Had I taken a trip of this area without this tour group, I’d have never gotten a real feel for the country and it’s people. This trip offered a hassle free complete experience. Meeting others from the group made it super enjoyable too. All the companies that provided tours of their facilities seemed genuinely happy to talk about what they do and share a bit of their world with us. We saw more and experienced more in a week than I could ever have imagined.”

Mark L.

“It was a stupendous experience – a perfect blend of new friends, conscientious and knowledgeable guides, and a collection of incredible insights into Italian culture and landscape.”

Jim W.


  • Cost Per Person: $4,050
  • Single Supplement: $750
  • Private Tour Minimum: 6
  • 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.

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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!
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 begin our ride through rolling hills, forests, and farmlands – much of it along a ridgeline – on our way to the town of Buonconvento. Just outside the town you will face your toughest hill of the day but the reward is worth it: our amazing agriturismo, a real working farm and vineyard where we stay for the night. We arrive at our inn in time to relax in the pool or take pleasure in our 360-degree view of the surrounding hillsides before walking across the fields to the dining room, where they serve us a delightful meal made with ingredients grown and raised on the property.
Biking Distance: 26 or 41 KM

Day 2

Today we ride to Pienza, an amazing hilltop town with a view over the entire Val d’Orcia below, one of the most famed valleys of Tuscany. 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. Once settled in at our hotel, we enjoy a tasting of Tuscan wines and cheeses (although it is in the center of wine country, Pienza is more well-known for its fine Pecorino cheeses!) on the hotel patio before sitting down to an al fresco dinner looking out over the valley floor. Afterwards, you might choose to take an evening stroll on the fantastic rampart overlooking the valley.
Biking Distance: 27, 43, or 67 KM

Day 3

Our ride today will bring us to Montepulciano, a wine town famous for its Vino Nobile, a luscious red wine that you will try during this afternoon’s included wine tasting! As we wander through the town’s historic streets, our Italian guide will offer his knowledge about the role Montepulciano played in Tuscan history. Those wishing to cycle in the afternoon can choose one of two loops back through the countryside to Pienza. One option includes a stop at Bagno Vignoni, a natural hot springs/bath, before returning to our hotel. Both routes allow you to stop for a gelato at a shop in Monticchiello that offers the best view of any we’ve ever visited! This evening, we enjoy a guided nighttime walking tour of town before our dinner at a local trattoria and an optional Limoncello (the classic Italian after-dinner drink) at a local taverna.
Biking Distance: 27, 41, or 55 KM

DAY 4: This morning we’ll transfer by private bus from Tuscany to another part of Italy – Umbria. In the quaint town of Torgiano, one of the centers of the Umbrian wine industry, we’ll reconvene with our bicycles and pedal our way blissfully to our next destination. En route, we’ll find a few small towns to visit and in which to enjoy lunch. Wandering through the flat Umbrian Valley will feel like a cakewalk after riding the Tuscan hills. The biggest challenge of the day will come on our short uphill ride to the town of Spello, a typical Umbrian town located on the edge of Mount Subasio and looking over the Umbria Valley. This will try your legs but please your soul when you see the fantastic views you have earned. Our four-star hotel is “home” for two nights and a multi-course dinner is just a short walk down the beautiful cobblestoned streets of town. We recommend a bedtime gelato on the return stroll to the hotel.
Biking Distance: 29, 45, or 51 KM

Day 5

Today you’ll find out why we love to bike in Umbria! From our front steps, we’ll have an incredible, mostly-flat ride across a hillside through olive groves, to a family run olive oil mill where we’ll have a tasting and learn how different grades of olive oil are made. Bruschetta with fresh olive oil is amazing! From there, we cycle to the famous town of Assisi, known mostly for its famous son, Saint Francis of Assisi. Even with its masses of tourists, Assisi boasts much more than its storied history and is a perfect stop for lunch and a little exploring through its winding streets. After lunch, our route takes us to the charming walled town of Bevagna and then on to the Arnoldo Caprai Winery, where we have a chance to savor the Umbrian wines and compare them to their Tuscan counterparts. We shuttle (or ride) back to our hotel, where you can choose to relax or explore town.  Tonight’s dinner is on your own in the lovely town of Spello.
Biking Distance: 22, 34, or 56 KM


We depart Spello this morning and all ride, on one route or another, to our final destination of Spoleto, perhaps the most “real” town of any we visit on this trip. Those looking for a challenge can choose to take side trips to Montefalco (center of the famous Sagrantino wine) or Trevi. Whether you choose to take part in the optional afternoon hike to the colossal and original Roman aqueduct, unwind at the hotel, or shop for souvenirs, you will find Spoleto alive with energy! Tonight we celebrate our last night together by taking part in a private Italian cooking class in our hotel and then feasting on what we have prepared together. Nobody will go hungry tonight!
Biking Distance: 38, 47, or 64 KM

Day 7

After breakfast, several possible loop rides will take you out of town and into the rolling rural countryside. These are actually some of our favorite rides for the empty roads and beautiful scenery. Upon your return, there will be time for a shower and then a walk to the train station, where your luggage will be transferred and we will bid one another farewell.
Biking Distance: 17, 32, or 38 KM

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Trip Accommodations


Set in the magnificent pristine countryside of the Siena hills, this century-old property is comprised of beautifully refurbished farmhouses.


This new brick and stone building overlooks the marvelous countryside of the Orcia Valley, yet is in the midst of the historic center of Pienza. The rooms and veranda are lovely but it is really Marco and his family that make us feel like we are home.


Dating from the 17th century, the four-star Palazzo Bocci sits right on the main plaza in the town of Spello, one of the most charming medieval towns in Umbria. From the fountain in the entrance to the detailed frescos on the ceilings, to the hanging garden, you’ll appreciate these small details of this beautifully restored property.


This small, charming hotel is family run and features a central courtyard, an 18th-century fireplace, antique furniture and Carrara marble in each bathroom. The fact that it is right inside the city gate makes it easy for us to get to and from on our bicycles.

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Arrival & 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 Spoleto train station after 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 recommended you travel by train or bus to Siena from either the Rome (airport code FCO) or Florence (FLR) airport. 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.

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. We like these should seasons because they tend to have the best weather and fewer crowds.

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.


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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