Across Italy E-Biking or Biking Adventure

Day 1: FANO to URBINO

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

Day 2: URBINO to SANSEPOLCRO

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

Day 3: SANSEPOLCRO to CORTONA

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

Day 4: CORTONA to PIENZA

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

Day 5: LOOP RIDE OR REST DAY

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

Day 6: PIENZA to RELAIS SAN LORENZO (OPTION SANTA FIORA)

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

Day 7: RELAIS SAN LORENZO to SOVANA

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

Day 8: SOVANA to PORTO ERCOLE

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

Day 9: CIAO CIAO!

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.