Day 1: Chianti loop

Arrive in Florence for the start of the tour. Our first Villa Hotel is just outside Florence in the Chianti region of Tuscany. After building the bikes take an easy spin or relax by the pool. Tonight we will have an orientation dinner prepared by the hotel chef, pass out tour clothing, and discuss our routes and planned adventures.

Day 2: San Gimignano out-and-back / Chianti wine tasting

Today, we ride through the vineyards to the medieval hilltop town of San Gimignano, where you can visit the famous Belle Torriâ city well-known for its history, arts and culture and situated on the Tuscan Hills. San Gimignano is one of our favorite hill top towns and a great spot to eat Gelato (Italian ice cream). Later we will visit local vineyards, sample some local wines and have dinner out at a fantastic Tuscan Trattoria.

Day 3: Siena

Ride through Chianti to Siena, one of Tuscany’s most famous and romantic Renaissance towns. Surrounded by olive groves and vineyards, Siena is one of the most amazing and beautiful cities of Tuscany. The town is built on three hills and surrounded by well preserved walls, it is filled with ornate Gothic architecture and has one of the world’s most unique piazzas – il Campo. This piazza is the spiritual and visual heart of the city where for centuries the neighborhoods of Siena have competed with one another in the world famous “il Palio” an all out bareback horse race around the square. Enjoy an evening coffee in the piazza and watch the world go by. Tonight we will have dinner at Il Nonno (Grandmas Restaurant) a long time tour favorite.

Day 4: Pienza

The ride from Siena to Pienza immerses you in the true beauty of the Tuscan landscape. You will ride though the very well preserved renaissance town of Asciano. Here you can stop by a local café for an espresso, then we will be on to Pienza. Often described as the “ideal city” or the “utopian city”, it represents one of the best planned of Renaissance towns. It was built on request by Enea Silvio Piccolomini, who was Pope Pio II in 1458. Pienza is located in the centre of the Val d’Orcia, a wonderful and untouched valley. The main piazza is the foundation for the town. (Its success as a “center stage” can be seen in Romeo and Juliet directed by Franco Zeffirelli) Strolling through the charming neighborhood, you will find street names such as Via dell’Amore, Via delBacio, Via della Fortuna” or “Love Street”, “Street of Kisses”, “Lucky Street”. The streets are also filled with craft shops, restaurants serving typical Tuscan fare, and shops selling cheese and wine. For tonight’s dinner you are free to discover a the local restaurant on your own. A favorite pleasure of the day is to enjoy wine and cheese on the outer wall of the city over looking the Tuscan valley at sunset.

Day 5: Orvieto & Val D’Orcia

Val d’Orcia, dotted with cypress trees and traversed by the ancient Roman road called the Francigena, is one of Tuscany’s best-preserved natural wonders. It has become known all over the world as the classic Tuscan landscape. The UNESCO World Heritage List recognizes Val d’Orcia’s extraordinary beauty and its inspiration and prominence in landscape painting. Films like the Oscar winners The English Patient, La Vita è Bella and Gladiator were shot here, as well as Romeo and Juliet, and Under the Tuscan Sun.

Our destination for today is Orvieto, a very unique and interesting city. As you approach Orvieto and see the town from a distance, it rises on a plateau of volcanic tuff, surrounded by a landscape of fields and vineyards. The natural yet unbreachable walls appear to encircle the city rather than elevate it as though it were a fortress rising above the flat valley floor. Our hotel is located in the center of town. You will want to take a stroll through the narrow streets, visit the famous Duomo, and enjoy local wines and some of the many wine bars.

Day 6: Viterbo / Visit the Civita di Bagnoregio

From Orvieto we will ride to the hidden treasure of Civita di Bagnoregio.This tiny city was recently featured in Conde Nash Traveler Magazine. The town hovers 1,440 feet above sea level on bare rock that has eroded so much the only way in or out is by way of a steep footbridge traversing an abyss. This little town is truly a site to see. The van will be waiting here for you with your walking shoes so you can explore this little gem. After our visit we continue the ride through quiet forested roads to our four star hotel in the little town of San Martino, just outside of Viterbo.

Day 7: Viterbo to Ladispoli

Ride through the country side of the Lazio region amongst the ancient Etruscan ruins. We end today’s ride on the southern coast of Italy in the sea side resort town of Ladispoli. After your ride have a refreshing dip in the pool or in the waters of the Mediterranean Sea. Tonight we will have a farewell dinner celebrating our journey though Italy and new friendships

Day 8: Departure

After breakfast it will be time to say good bye. From here you can take a shuttle to the Rome Fumacino (FCO) airport or the train station in Ladispoli. You may want to extend your vacation with a visit to Rome or go back to Florence. We can assist you in making reservations for hotels and walking tours to complete your stay.