Across Italy E-Biking or Biking Adventure

May 13 - 21, 2023

“I chose each of the routes for their scenic beauty and lack of road traffic as well as for the incredible variety of food, wine, culture, and landscapes they offer.”
GIOVANNI RAMACCIONI, OUR TUSCANY-BASED GUIDE for the italy e-biking or biking adventure

A nine-day tour across Italy via e-bikes or bikes – there is a lot to talk about here and a lot to experience over there!

E-Biking or Biking Across Italy?

First off, let’s talk bikes and difficulty level. E-bikes have been around since the late 1800s but it is only in the past few decades that they have become widely available. Then, during the pandemic, bicycling boomed and e-biking boomed along with it.

They have also become increasingly popular on our biking tours, for multiple reasons:

  • They allow couples or friends who are not at the same fitness level to cycle together
  • They have multiple gear settings, so you can get a lot of boost or none at all, depending on how much you want to workout
  • They eliminate walking your bike up steep hills which, in all honesty, most of our travelers have had to do when cycling in Italy

On this tour, there are definitely hills and e-bikes are a great way to conquer them. Therefore, this tour is really for bikers of most ability levels. We expect most of our participants to be on an e-bike – and you can always turn off the electrical boost when you want. However, regular bikes are available for those of you into your riding!

The Route Across Italy

Not only is this nine-day tour (eight days of riding) take us across Italy, but it takes us across one of the most beautiful areas of Italy. Centered on the region of Tuscany, we actually start on the beautiful Adriatic coast, go through the heart of Tuscany, and end on a peninsula sticking out into the Tyrrhenian Sea, which connects to the Mediterranean.

We meet in the seaside resort town of Fano on the Adriatic coast, which still has ruins from its Roman origins. We visit amazing cities such as Urbino, Città di Castello (where our guide Giovanni lives), Cortona of Under the Tuscan Sun fame, and Montepulciano. We end in a small seaside town on the slopes of Monte Argentario on the opposite coast. We move each day except for two overnights in Montepulciano, one of the most amazing cities in Italy. Our routes throughout are designed to minimize traffic and maximize scenery.

The Food and Wine

The food and wine in all of Italy is superb but this area is known as both a major wine region and a bread basket. We’ll enjoy seafood at both the start and end of the tour. We’ll taste the local pecorino cheese in Pienza and the Tuscan-style pici pasta. We’ll taste the Montepulicano, Brunello di Montalcino, and other wines sourced from vineyards we pass en route.

Join Us On Our Across Italy E-Biking or Biking Adventure

We love this area of Italy and know you will too. It is a big commitment of nine days but well worth the investment! Join our May 13 – 21 pubic tour in 2023 to meet other cyclists and Italy fans or gather your own group of eight for a private tour on a date of your choosing.

Private Tour Info

You can book this as a private tour choosing your own dates with a minimum of 8 participants.

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Other Info: > E-bike rental €50 per day. Bike rental €30 per day.

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Trip Highlights

  • Bike across Italy from one coast to the other!
  • See the sights of two Regions (Marche and Tuscany) and four different Provinces (Pesaro and Urbino, Arezzo, Sienna, and Gresseto)
  • Enjoy the option of an e-bike with multiple gears, allowing you to choose your level of exercise each point along the way
  • Taste Montepulciano and Montalcino wines, try pecorino cheese, feast on pici pasta, and luxuriate in seafood from both coasts
  • Visit the superb towns of Urbino, Sansepolcro, Cortona, Montepulciano, Pienza, and more

You can arrive to the seaside resort town the day before to enjoy the area, explore the ancient Roman ruins, and prepare for our tour. Our Guides will meet you in the morning for introductions and to pair you with your rental e-bike or standard bike. Most of today's ride is relatively flat, taking place on the land that extends from the coastal beach as we move inward and across Italy. Near the end, there will be a steep rise to the city of Urbino, which will either be a serious workout on a standard bike or, if you have elected to rent an e-bike, a joy as you get that electric boost. Make sure to turn around and take in the expansive views of the coast behind you. Urbino is a magnificent medieval and renaissance town - a place of architectural and artistic masterpieces. After you shower you can choose to visit Mondavio, the Palace of the Duke of Urbino, or simply hang out in the historic center.

Total Distance: 67 KM


Today in the morning it is mostly small rolling hills as we make our way to the medieval town of Sant'Angelo in Vado, , before we descend down to the Val Tiberina. We will pass beautiful countryside and small towns, including the medieval S. Angelo in Vado, a great place to park your bike to wander the streets and perhaps grab an early lunch. It is then a long uphill climb up the Appenines to the Bocca Trabaria pass (again, that electric boost!) before we head down to the Val Tiberina, with an optional stop at the Hermitage in Lamoli on the way. We reach our valley town of Sansepolcro, a fantastic small city with one of the most beautiful Corsos (main street laid out by the Romans) in the region. Our guide, Giovanni, has his base here. Note: It is possible we will stay in the nearby Citta di Castello (City of the Castle), where Giovanni lives, depending on hotel availability.

Total Distance: 68 KM


Today we cycle over another small range of the Appenine Mountains, the long set of mountains running along the eastern side of Italy from north to south. We have a long gradual rise at first to top the mountains and then an equally long descent, with views of Lake Trasimeno and the Val di Chiana as you go. Finally, we face a sharp uphill climb to the hillside city of Cortona. Cortona, of course, is famous as the site of the book and move Under the Tuscan Sun. It is a lovely city with a fantastic central historic area and a perfect place to enjoy a coffee or glass of wine after the ride. Cortona is our base for the night and is the start of our time in what we consider the heart of Italy.

Total Distance: 72 KM


Today is a day dominated by hill towns. We start with a ride down from the hilltop city of Cortona. We then have a relatively flat to rolling section across beautiful plans and utilizing a paved bicycle path. It is then up, up again to the small city of Torrita, once a fortified city that protected Siena, with remains of its walls still visible. The small historical center is well worth walking around and is a good place for lunch. We then continue on to the town of Pienza, the town planned by Pope Pius II with its balcony looking over the valley below and home to pici pasta and pecorino cheese. Our hotel for the night has an excellent garden overlooking the valley below and is a superb spot for enjoying a glass of wine as the sun sets.

Distance: 60 KM


If you choose, you can opt to rest your legs, sleep in late, and wander the small streets of Pienza. Or you can hop back on your bike / e-bike to do a loop ride through what is the most beautiful region of Tuscany, one of the most beautiful regions of Italy. Our ride today is a loop taking us from Pienza to Montepulciano to the small village of Monticchiello and back to Pienza. And we will tempt you at every step of the way. Outside Pienza we'll do a tasting of Pecorino cheese. Montepulciano is one of the most well-known villages of Italy and is famous for its Vino Nobile di Montepulciano wine; we'll have a formal wine tasting in an ancient wine cellar beneath the city. In Monticchiello you can stop for lunch at one of several restaurants with verandas overlooking the valley below. All this takes place in and above the Val d'Orcia, which is classic Tuscany postcard perfect. And as an option, you can continue to the town of Bagno Vignoni, famous for its Roman-era baths heated by local hot springs. Dinner tonight is on your own in Pienza.

Total Distance: 56 KM


Today we engage in a shorter but epic ride on the slopes of the ex-volcano Mt Amiata, passing through olive groves and durum wheat fields to the chestnut woods of Amiata. Monte Amiata is an important part of Tuscany but less well known. It is a dormant volcanic mountain that separates the Val d'Orcia where we were this morning from the Maremma area where we are headed tomorrow. The Amiata area is rural and less touristed than other, more famous regions in Tuscany. There is a good deal of up and down today and, by this point, you will likely be loving your e-bike's electric charge assist. We stop early in part because our destination is the Relais San Lorenzo, a beautiful hotel located in the country with an incredible outdoor swimming pool. This is a great day to have a short ride to luxuriate in the hotel. However, you can always opt to continue on to nearby Santa Fiora, a small village of only 2,500 people. It is perched on the slopes of Monte Amiata, has a walkable city center, and you can enjoy the sounds of the Fiora River running through. Arriving in town, you'll want to spend an hour or so just wandering and enjoying real Italy. One stop to make is the gardens around the local peschiera, a reservoir for trout breeding generally created in Roman times.

Total Distance: 43 KM


There are a few uphills today but in total the downhills are twice the elevation loss as the uphill gains. We are heading back down and towards the western coast of Italy. By the time we reach the area of Maremma, the riding is flat. Maremma is the most southwestern portion of Tuscany and was previously marshlands until it was ordered drained by Ferdinando I de' Medici. The area is known today for its cattle and horse raising but it was in ancient times home to the Etruscans, a national of city-states that dominated what is now Italy in the 8th to 5th centuries BCE. (The Romans called them the Tyrrhenians, hence the name of the sea to which we are heading.) On our route we'll have the opportunity to soak in the hot springs of Saturnia, try a glass of the local Morellino di Scansano red wine or the Bianco di Pitigliano white wine, and walk the remains of city walls laid out by the Etruscians in Pitigliano. Our destination is the town of Sovana, listed as "one of the most beautiful villages of Italy."

Total Distance: 53 KM


The first part of our ride day has a few distinct but moderate ups and downs, follwed by a long downhill to the coast. On our route we'll pass through towns such as Manciano and Capalbio where you can stop for a coffee or gelato. As we reach the coast, the riding flattens out and we head out on a flat isthmus that eventually reaches the peninsula on which stands Monte Argenario, surrounded by the Terrenian Sea. Upon arrival, you can check in, shower, and go for a nice exploratory walk in the old town of our home for the night, Porto Ercole, and along the harbor. Tonight is our final dinner together and we will celebrate our accomplishment of riding across Italy from coast to coast!

Total Distance: 77 KM


We will have breakfast together and say our goodbyes. With a short shuttle to the local train station, you are free to continue your journey or start on your road home, with incredible memories stored away.

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Trip Accommodations

The hotels on this tour will depend on the number of people participating in the public or private tour. For small tours of eight or so people, we have the ability to choose smaller accommodations. For larger tours, we focus on amazing hotels both in cities and in the countryside.

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Arrival & Departure

We will meet at a designated hotel in Fano on the eastern coast of Italy at 9:30 AM on the first day. The easiest way to reach Fano is to fly to the major airport of Bologna (two to 2.5 hours by train to Fano), Florence (three to four hours), or Rome (4.5 to five hours) and take a train from there to Fano, where the station is conveniently in the center of town. Our suggestion is to fly into one of these cities and spend a night or two before the tour and then to arrive in Fano the day before we meet.

We depart after breakfast from Porto Ercole with a 15-minute shuttle to the nearby train station. From there you can reach Florence (3.5 hours) or Rome (two to 2.5 hours), the two preferred departure airports.

  • Two Zephyr guides (one local) accompany each trip, with a third added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, you may ask us to find a traveler to share a room with you but will need to pay a single supplement to have your own room if we cannot match you.
  • Six dinners (one dinner on your own in the town of Pienza) and all breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches 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, bike rentals, and travel to and from the destination.
Best time to visit

We like the shoulder seasons of spring (April through June) and fall (September and October) because there are fewer tourists and more pleasant temperatures than in the months of July and August. You will have greener fields and more daylight in the May through June time frame but ripe vineyards and golden wheat fields in the fall.

Extending your vacation

We definitely recommend arriving to Fano one day early for the 9:30 AM start on our first tour day. It can be really nice to spend a night or two in your airport arrival city of Bologna, Florence, or Rome. If you have more time than that . .. well, Italy has so much to offer. A major decision is whether to travel in Italy by train (best for the larger cities) or car (better for rural areas). We love the nearby city of Siena and the fun hilltop towns of Umbria.

Ability Level

This Adventure is rated Moderate due primarily to the planned use of e-bikes. E-bikes are great and have some awesome advantages. They turn the hills of this route into very manageable aspects of the ride. If you wish to test yourself, however, you are more than welcome to ride a standard hybrid or road bike!

Type of people who will enjoy this tour

This adventure is ideal for those who like to exercise on vacation but are not up for climbing big hills on a bicycle. We expect some of our travelers to have been to Italy before and possibly even to a few of the towns on this tour - but this is a great tour to get you Italy fans into areas you would never otherwise visit.

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience.

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