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If Italy is thought to be the center of the universe for cyclists, then Tuscany must surely be its glowing sun. Much of what has made Italy famous has come from these rolling, vineyard covered hills. Art, architecture, music, science, food, and wine; Tuscany has given us some of the best. A history of war and strife has shaped the buildings and the cities, the Renaissance has shaped the art and architecture, and a love of life has colored the food, the wine, the cafés and restaurants.

Volterra, San Gimignano, Siena, Arrezzo; as we cycle from city to city, we celebrate the journey as much as we do the destinations. Cyclists are held in the highest esteem in Italy, and these are the routes of the celebrated ones; small winding roads, rolling hills, farmland and forests, hamlets and villages, vineyards and churches. Each pedal stroke is a destination in itself. When the ride is done, the journey is still in progress with every city begging exploration, every plaza teeming with life, every café demanding your presence, and every alley leading you to more surprises. Our hotels, whether in the heart of the city or deep in the countryside, are some of the best that Tuscany has to offer.

Ride, feast, relax, rest, and wake up for the next day’s adventure.



We’ll meet you at the Pisa or Firenze airport (your choice) and transport you to our hotel in nearby You’ll have the rest of the day to assemble bikes and tandems (plenty of help provided), explore the village, or take a nap. Tonight we’ll enjoy a get-acquainted dinner followed by an overview of the tour.

Sept 2- VOLTERRA 35mi, 3000ft

Like all of Tuscany, the route is mostly rolling hills, and today, the biggest hill is saved for the end. The walled city of Volterra is built on top of the grandest hill in the vicinity, some 1500 ft above sea level. To get here, we will be riding on small farming roads past forests and recently harvested fields of hay, where we may see the occasional red poppy which escaped the blades of the combine. As we approach from a distance, Volterra is most impressive, commanding a position which was easily defended during times of strife. But inside its walls, it is full of life and most inviting; a visit to one of the sidewalk cafés for a cool drink is a must - as it will be every day at ride’s end. Dinner will be Albergo Villa Nencini in Volterra.

Sept 3 – SASSETTA 34mi, 1300ft

Swooping down from the walls of Volterra to the valleys below is just one of the delightful treats in store today. As we ride toward the sea through farmlands we’ll see the landscape change from wheat fields and sunflowers to vineyards and olive groves. Here, we enter a region renown for its fine wines and delicious olive oils. Meandering through cork tree forests and olive groves towards our country villa, we stop at Restaurant Zi Martino for a simple but tasty lunch. This is the winter eatery of many a pro cycling team and the local hangout for Andy Hampsten and his tours. After lunch, we slowly pedal up the hill through Castagneto Carducci toward Sassetta; although a stop in town for gelato always seems like a fitting treat for such a fine day. Continuing above town we begin riding along one of the most beautiful roads for bicycles in all of Tuscany. A gentle climb brings us to the best part, the winding, cork tree shaded road to our hotel. Our villa, situated amidst a splendid 150 acres of meadows, orchards, olive groves, and forest, has an incredible location, where we’ll be treated to superb hospitality and delicious meals.

Sept 4 - SASSETTA Loop ride, 26mi, 1650ft, or 40mi, 3000ft, or 41mi, 1600ft

When Andy Hampsten rode as a professional cyclist, he lived and trained in the coastal hills around Castagneto. When he retired from racing he bought a farm in this region and continued to ride all the roads in this area. Today’s morning ride is along his favorite training route. We head to Monteverdi then down the Cornia Valley to Suvereto and back to Sassetta. Bolgheri is very famous for its wonderful olive oil, but it is also highly respected as a grape growing region. Not as well known as Chianti or Brunello, the Bolgeri D.O.C. produces some of the very best red wines in all of Tuscany as well as great rose and white wines. To fully appreciate the tasty treasures of this region, we’ve arranged a visit to a specialty olive oil producer, where we’ll lunch on a medley of local produce and breads flavored with delicate olive oils from the presses of our hosts. After our feast, we’ll have the opportunity to purchase bottles or huge tins of olive oil. Don’t worry; the van will be along, so you don’t have to lug your purchases up the hill to Sassetta.

Sept 5 - MONTIERI 44mi, 3900ft

Heading out this morning, we retrace yesterday’s route along the winding cork road to Suvereto. Leaving the coastal area, we cycle through vineyards and olive tree groves on a small country road on our journey to Massa Marittima. Climbing up to Massa we’re able to view this jewel from many sides, finally arriving in the star-shaped Garibaldi square, dominated by the recently restored 13th century Duomo. Numerous sidewalk cafes and gelaterias will tempt us to consider a light lunch before leaving town for the final climb to our rifugio in Montieri. Situated high above the Tuscan valleys surrounding the Poggio di Montieri (1037m), we’ll settle in to enjoy dinner and a crackling fire in the great room of the rifugio.

Sept 6- MONTALCINO 51mi, 3200ft -or- 59mi, 4500ft

The first half of today’s route is through rugged, forested hills, while the second half is along vineyard-covered valleys. The wineries in this area produce some of Italy’s best tasting wines, but they are not as well- known as some of the more famous wines. The long route takes us along more winding, peaceful farming roads, to Porrona, a small walled city and monastery, which has been recently restored to its original beauty. Our hotel is on the northern edge of town, hanging precariously over the valley far below; the view from the pool is spectacular. As one of the best hilltop villages in Tuscany, it will be a delight to wander the small streets and investigate the many small shops with friendly proprietors and great values on wine olive oil, and other locally made items. Since the hotel is without restaurant, dinner will be on your own tonight.

Sept 7– MONTALCINO Loop rides up to 66mi, 6700ft

Montalcino is a wonderful medieval city made famous by the Brunello wine grown on the hillsides surrounding the town. This would be a great day to wander the cobbled street sand alleys, stopping occasionally to taste wine in one of the many ‘enoteca’ (wine shops). There are many good restaurants for lunch, and of course gelaterias to tide you over till dinner. For those who want some good cycling, there are amazing bike routes. A long descent from Montalcino brings us to the base of Italy’s second tallest volcano, Monte Amiata. Here the roads wind and climb through forests and farm lands from village to village; the higher you get, the bigger the views. For those wanting an easy bike ride, there is a wonderful destination. The Monastery of Sant’Antimo is 6 miles from Montalcino. The church is quite beautiful. If you time your visit, you can hear catch the morning light coming through the tall windows and then hear the famous Gregorian chanting of the monks at 12:45pm. It is about 1hr 45min walk from the hotel, with plenty of opportunities for photos.

Sept 8 - CORTONA 55mi, 3900ft

We’ll cycle through some of Tuscany’s most famous towns; San Quirico d’Orcia, Pienza, and Montpulciano. Pienza is truly worth a long visit; built by Pope Pius II in his own honor, this walled town is a model Renaissance town. The Etruscan town of Montepulciano with its 8th C fortress is the perfect location for lunch, where you can enjoy a little shopping or people watching before continuing your ride.. The route is quite scenic with plenty of beautiful views along the way, including the cypress-lined twisting road to Monticchiello. The most impressive view is saved for last. Cortona is one of the outstanding jewels among Tuscan towns; it sits high above the valley floating in the clouds, when they are present. Cobblestone streets climb to the Medici fortress, where the views are enormous in all directions. We’ll dine on our own both nights at any of the fine little restaurants in town.

Sept 9—CORTONA rest day or 31mi, 3200ft, or 54mi, 4900ft

Cortona is a bustling Tuscan village, recently made famous by Frances Mayes. But there is a good reason this has happened. Not only are the city and the surrounding hills very beautiful, but the people, the shops, the street markets, everything is so full of life. This is best experienced in the evenings when it seems every one in town is strolling along the main pedestrian walkway, greeting the shopkeepers and their friends, having a drink at one of the many bars, before having dinner at one of the restaurants. After dinner, the younger folks come out and start their socializing, keeping the center of town busy until late in the evening.
The Umbria loop ride takes us over a series of forested hills then above the shores of Lago di Trasimeno, Italy’s largest lake. The quiet roads and peaceful vistas are rewarded with a sense of going back in time to a simpler way of life. We pass beneath an ancient castle while in the distance we hear the hunters and their hounds scouring the forests for cingiali (wild boar). Dinner tonight is on your own, so while walking about town, be sure to make reservations for dinner at any of several charming restaurants, as the best places fill up early. But first we’ll enjoy an informative wine tasting at our favorite shop next to our hotel.

Sept 10 - ANGHIARI 43mi, 1500ft, or 49mi, 4100ft

As we leave Cortona we pass the pink villa and gardens of Francis Mayes, author of Under the Tuscan Sun and other books on life in the region. After a gentle climb we will enjoy one of the longer winding descents of the tour. Here we are venturing into Umbria, and will be enjoying the same scenery and sights as in Tuscany; majestic medieval towns, beautiful hills and valleys, and of course just wonderful cycling. Three cities of note are Monte S. Maria, Monterchi, plus our destination town of Anghiari.

Sept 11 - REGGELLO 48mi, 3000ft, or 62mi, 6600ft

Two completely different rides are available today; one easy, one hard. The first takes us west over a small pass and descends to Arrezzo; this is a great shopping town, especially for jewelry and antiques. With so much to see and do here, you can easily stay well past lunch. The remainder of the ride is down the Arno river valley, except for the last 5 miles up to Reggello. The long route is for those who enjoy a little climbing. First is the scenic ride up the slopes of Monte Penna to Caprese Michelangelo, where we can view Renaissance furniture, books and reproductions of the great artist’s works. Continuing on we arrive in Bibbiena just in time for lunch; then afterward we’ll climb the Passo di Consuma. From here it is all downhill to Reggello on lovely winding roads through wooded hills.

Sept 12 - SAN LEONINO (SIENA) 42mi, 2500ft or 50mi, 4900ft

Chianti is a geographical, as well as oenological name - both describing something splendid! The wine produced in this region is certainly the most notable in Italy, and the hills and vineyards are feasts for the eyes; it is best to savor these pleasures slowly, enjoying every last taste. Our first sip of Chianti will be in the town of Greve, considered to be the capital of this area. The specialty wine shops are very much worth a visit, and we’ll plan to have the van nearby to carry any purchases that don’t fit in your water bottle holders! The next stop is Badia a Coltibuono, an 8th century abbey, which is currently occupied by a winery and restaurant; lunch here is strongly recommended. Save coffee and dessert for Radda, whose location among the steep hillside vineyards is quite spectacular. The last village before descending to our hotel is Castellina, officially designated as yet another of Tuscany’s most beautiful villages. The very best gelato in all of Tuscany is found here in Castellina. After dinner, we might sneak back to Castellina for another mouthwatering taste.

Sept 13 - SAN LEONINO (SIENA) 0 - 16mi, bike, bus, taxi, or van to Siena

There is no riding planned for today, other than the 8 miles to and from Siena. Next to Florence, Siena is the most famous city in Tuscany, but is considered the most beautiful of all in Tuscany. The architecture demands scrutiny, with palaces, churches and towers dominating the skyline, and the cathedral is certainly one of the most delightful, decorative ornaments in Christendom. History oozes from every nook and cranny; life here is special, and always has been. The narrow streets are filled with people strolling from shop to shop, stopping for a quick cappuccino, and talking animatedly with friends along the way. There is so much to see and do here that one day is not enough. If you do nothing else, you will find the Campo, the central plaza, perhaps the most impressive plaza in the world. This is truly the heart of the city, the center of life in Siena. Enjoy!

Sept 14 – MONTOPOLI in VAL d’ARNO 54mi, 3400ft

We’ll start the day with one of the best descents of the tour, 19k of high speed, gradual, winding downhill from Castellina to Poggibonsi. Next on the agenda is the well preserved medieval city of San Gimignano, one of Tuscany’s most striking tourist attractions, with its 16 remaining towers and its wonderful open walkways and plazas. There are interesting shops and plenty of excellent restaurants for lunch. A few miles past San Gimignano is the pizza restaurant where some of us enjoyed pizza on the first day. From here we are faced with a long downhill and the final climb to the hotel, where we will have plenty of time to pack bikes and share stories of today’s ride. Farewell dinner tonight is at our hotel.

Sept 15

Van transport is provided to Pisa or Firenze airport.