• Dates: May 4 - 10 2018
  • Trip Length: 7 Days & 6 Nights
  • Activities: Biking
  • Guides: TBD
  • Cost: $2,950 per person
  • Optional Single Supplement: $750
  • Difficulty: Moderate

Other Info: Bike rental E25 per day.
E-bike rental E40 per day.

“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 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 (see below).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.


Those of you who have already taken a biking (or skating) tour with us know that following written route directions is necessary for the freedom of enjoying the trip at your own pace – you certainly don’t want to have to keep pace with the fastest person in the group, nor do you want to wait all the time for the slowest person! Because you’re armed with directions that tell you exactly where you need to go, you can stop to take photos or eat lunch whenever you want – this is your vacation, after all!

Some people are just not that great at reading maps or directions – which is okay! We are taking the guesswork out of route directions by adding a GPS unit to our bicycles, with the routes pre-loaded, so all you have to do is watch or listen for your next turn. This will eliminate the need to track exactly where you are on a page and read as you ride — you’ll simply need to follow a line on a map, and not worry about getting lost or going off course! This has revolutionized our biking tours and we are thrilled to be able to offer this new technology to you.

Daily Itinerary

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 on our way to the town of Buonconvento. Just outside the town you will face your toughest hill…SEE FULL ITINERARY

For More Information

  • See Frequently Asked Questions for this specific trip.
  • See our General FAQs page for general tour questions.
  • INTERESTED IN JOINING US? Call us at 888.758.8687 or email us to check availability, or to ask any questions you may have regarding this trip or any other travel ideas you may be considering.
  • TO BOOK YOUR ADVENTURE: You can book online or by calling us at 888.758.8687. Zephyr Adventures requires a 500 deposit (payable by check or credit card) at the time of booking. The remaining balance is payable by check or credit card no later than 60 days prior to the start of the trip.

  • WHAT HAPPENS NEXT? We will send you a confirmation email after we receive your booking, as well as a link to detailed printer-friendly pre-departure documents: arrival and departure information, suggestions for making travel arrangements, a packing list, an invoice, information about your trip location and guides. It will also include a link to an information form and liability waiver. We will also provide you with a link to information about travel insurance. We highly recommend you purchase travel insurance because it protects you if you have an unexpected change in travel plans.  Please do not purchase airfare until you have received your pre-departure documents.

“Favorite Moment: The wonder of experiencing my first hilltop Tuscany village in Montepulciano; the visit to the olive farm-production facility; the wine tasting in Spello; the pink and white limestone and basilica in Assisi; the food; the kitchens; managing to keep up with Giovanni on a bike ride, the escalators and aqueduct in Spoleto; how the guides became a part of the group. My favorite moment lasted for seven days.” – Dan M.


View all Tuscany & Umbria photos

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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!

Trip Accommodations

Night 1 >> Pieve a Salti / Siena

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

Nights 2 & 3 >> Piccolo Hotel la Valle / Pienza

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.

Nights 4 & 5 >> Hotel Palazzo Bocci / Spello

​ 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.

Night 6 >> Hotel San Luca / Spoleto

​ 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.

Travel Details

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.