Day 1
All Roads Lead to Rome, Some are just better than others

Be ready Be ready to ride as a short transfer from the busy streets of Florence is the start of our first ride following the quiet country paths into the wondrous Chianti countryside. One moderate climb allows us to fully enjoy the wonderful views of this famed wine region as well as explore the nearby Abbey and enoteca. Our destination is a beautifully restored farmhouse winery located near an ancient market town in the heart of the Chianti Classico region. Here we get a chance to relax and explore the grounds with a welcome glass of Chianti/Rose or laze around the farms impressive vanishing edge pool before we sit down for a memorable Tuscan feast--Florentine T-bones anyone?

• Lodgings: family run farm/winery offering us the unique experience associated with the agriturismo.
• Dinner: Our farmstead has one of the finest kitchens in Tuscany--a favorite amongst locals

Day 2
Serious Wine Country

We begin to understand the storied attraction of this region as we bicycle along country roads and trails lined by oak groves, vineyards and farmlands. We pass through tiny villages of the region such as Radda in Chianti and may wish to sample the Chianti Classico along the way. We stop just outside the famed Castello d’Ama winery where we prepare a gourmet picnic for you that features specialties of the region such as finocchiona (fennel-salami), wild boar ham or pecorino sheep cheese.

Through the most picturesque and off the beaten track hamlets we pedal to the Castel di Brolio where the original Chianti blend was concocted. The Ricasoli family still makes use of the castle; however they have donated a portion of the grounds and outer buildings for the public to tour. We may opt to taste the Brolio wines before we make one last dash for incomparable Siena, home to the “Palio” horse race and what many think is the most beautiful square in the world. Once we enter the ancient gates of this town we discover a unique blend of Medieval and Renaissance treasures amongst colorful cafes and shops. Here we offer a guided tour of the city and Duomo.

• Lodging: An 18th century patrician villa converted into an upper 3-star hotel & set in a romantic garden.
• Dinner: Outdoor café on “Il Campo” Square

Day 3
Crete Landscapes, Abbeys & Pecorino Cheese

South of Siena we find ourselves back in the quiet countryside of vineyards, Abbeys, Roman baths and historic hill towns.  We travel through a strange landscape known as Crete, bare hills of deeply fissured ash gray clay soil.  Then before lunch, the secluded Benedictine Abbey of Monte Oliveto Maggiore appears suddenly on a hilltop within a grove of cypress trees. Founded in 1313 by Bernardo Tolomei, the Abbey’s cloisters are frescoed by Signorelli and Sodoma and the abbey is probably the most picturesquely situated in Tuscany.

We lunch while overlooking the ash gray, deep green or bright yellow hills. From here, small country roads take us to Pienza, a renaissance jewel that was not only named after Pope Pius II, but also built to his dreams of a perfect city. Depending on the time we can visit a village with a sulfurous hot spring in the piazza, a truly welcoming experience. It feels as wonderful today to soak in the soothing thermal baths as it probably was for the Etruscans & Romans in their time. For those that wish, we visit nearby location of where the “English Patient” was filmed.

• Lodging: 3*** at the historic town center.
• Dinner: free night out.

Day 4
Forgotten Tuscany

Today’s ride is dedicated to the lesser-known southern parts of Tuscany. Flocks of sheep dot the vast fields, ancient towers top almost every hill. A long stretch of flat terrain past a medieval castle is the perfect warm up for a gradual 3-mile climb through oak forrest and nature reserve. Once we reach the top the views expand over hilltop villages to the highest peak in Tuscany, Monte Amiata. After a well-deserved downhill we pedal along a rolling crest; this surrounding quiet beauty in this region is one of our favorite paths in Italy to ride. The houses clustered around the castle and the imposing quadrangular-shaped tower of the Bologna Palace soon appears within a foreground of oak forest and sheep herds within vast rolling pastures.

Our destination is an ancient medieval fortress town yet to be mentioned in guidebooks, however offers us the unique character Italy is renowned.  Relax in the early evening sun with a cool drink from the street café at the medieval gate. Then head for the luxurious spa whose restoration will just have been completed this spring. These springs are protected by the Church of the Madonna of the Baths, which dates back to the 11th century. Besides the healing qualities of these hot springs you can also enjoy massages, mud baths, facials J and more.

• Lodging:  In a beautiful 4 star Inn located just outside the medieval gates.
• Dinner: At Andiamo’s favorite trattoria

Day 5 & 6
“The Golden Lily"

After breakfast we get on our bikes and head to the southeast corner of Tuscany and into Umbria. Through tiny villages lost in the lovely countryside we come across hamlets and farmsteads that appear in the hills as they have for centuries. This ride displays the Tuscan and Umbrian countryside life that is far removed from all the tourism stops and fancy wineries. And here is the best part: after yesterdays rather challenging climb today it starts off DOWNHILL! Along the way we sample some of the fine Orvieto wines the region is known for producing. We are certain that the past 2 days of wild beauty in this corner of Italy will forever be etched in your memory as what rural life is all about here. Arrive in Orvieto in front of the golden entrance of the Duomo with plenty of options from which to choose to enjoy this magnificent city.

Orvieto, perched on a tufa plateau, is known for its beauty; fine wines, ceramics and Duomo, one of the most revered gothic cathedrals in the world. The wine produced from the fertile volcanic soils around town was once so highly regarded that the architects working on the Duomo were happy to be paid with it. We make sure to visit the outstanding Duomo that also hosts Signorelli’s “Last Judgment”, another great fresco period of his (you’ll have seen the one in the Abbey of Monte Oliveto Maggiore in Tuscany), as well as the 16th century well cut into the tufa on which Orvieto stands. By the way, it was Pope Leo XIII who described the Duomo as the “Golden Lily of Italian Cathedrals.”

On your free day we felt a day off the bike was well deserved however, we do offer a great ride that explores Cívita di Bangoreggio, a city perched on an isolated, rocky outcrop that's home to fewer than 20 people or at least was 2 years ago. This might be why: Civitia is also known as “la Città che muore” (“the city that is dying”) due to the erosion of the rock beneath. People have been emigration from here since the sixteenth century, leaving behind a dwindling population in a strange, eerily deserted village that is also inhabited by a number of artists from all over the world.

Our ride can be to your preferred distance as you can pedal as far as the shores of Lago di Bolsena or cut it short and take in these views from afar. We also offer a tour of the town’s underground Etruscan caves before your free night out.

• Lodging: 4**** converted palace in the medieval center
• Dinner: one free night in medieval center

Day 7
Old World Hospitality

After an afternoon off the bike we are perfectly ready for today’s ups and downs in terrain… Most of the day you find yourself riding in a countryside of olive groves, forest and green pastures, which has earned the title “Il cuore verde di”Italia” (the green heart of Italy).

From the Umbria region we pedal into the Lazio region and stop on the way to explore the Etruscan past and forgotten villages. These charming and friendly towns beckon you to sample the locale specialties on display before attacking the beech wood and chestnut-lined road leading up to Soriano. The exquisite hospitality, the fresh, clean air and the harmonious appearance of this town within an unspoiled natural environment made us immediately fall in love with Soriano. This is another one of those towns that only the Italians seem to know about.  As you wander the streets you are treated with a friendliness and curiosity that beckons for a return visit one day.  If you are lucky enough to be on our fall tours you will enjoy witnessing the annual chestnut festival. Our hotel faces the medieval town front that features a massive Orsini castle towering above the ancient rows of tall homes.

Lodging: small hotel facing the stunning rows of medieval houses; there is a 19th C. garden to relax.

Dinner: highly regarded, family run restaurant in the medieval town.

Day 8
All Roads Lead to Rome

Have you ever wondered where all the hazelnuts come from? Well, I always have J. In our morning ride lays the answer. You probably get to see more hazelnuts then you have ever imagined…

Through these orchards the small country and farm roads lead to ancient Sutri. Once the Etruscans lived here but then the Romans came along and kicked them out. They built an impressive amphitheater that we visit before lunch, at a trattoria we always go way out of our way to visit. From under the clock tower taste Italy’s best porcini mushroom soup. After one final great meal together we cross the ancient Roman road Via Cassia and climb the ridge from where views expand over Lago Bracciano and the lakeside villages, villas and gardens that surround it (location of the recent Cruise wedding). Shoot down to the chestnut lined waterfront and feel good about all the miles and terrain you have covered this week.

It is true that every road leads to Rome, but unless you‘re comfortable riding with the many trucks, mopeds and endless rows of fiats trying to get in you’ll more likely enjoy our shuttle into town from this lakeside. We get you to the nearest station boarding for the short transfer into the Roma Termini Station or other destination you chose. In your final tour packet we offer a self-guided itinerary and tips for best visiting Rome as well as a list of hotel suggestions. We are also glad to help with any onward tips for other parts of Italy for those traveling elsewhere.

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Transportation Logistics

The following is a list of train schedules for transportation to and from the tour start and end locations. Train departure times and tracks are subject to change, so verify before boarding.

*Meeting your tour by train if not staying in Florence:
Trains from Rome to Firenze/Florence (tour start): ~1.5 hours
#9310 Roma Termini -9:00am--arrival Firenze S. M. Novella ---10:37am

From Pisa: ~1 hour
#3110 Pisa Centrale -10:27 am--arrival Firenze S. M. Novella ---12:45 pm

From Milan: ~3.5 hours
#9433 Milano Centrale -10:00am-- arrival Firenze S. M. Novella ---12:45 pm

*Departure times and track are known to change on a moments notice, thus verify before boarding