Day 1: Chianti loop

Our first Villa Hotel is just outside Florence in the Chianti region of Tuscany. Chianti is nestled in the center of a valley surrounded by hills decked with woodland and vineyards, it is here that one of the most famous products of the area is produced: the world-famous Chianti Classico DOCG wine. 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 your tour clothing, 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 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. This town is filled with fine examples of 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 each year the neighborhoods of Siena compete with one another in the world famous “il Palio” a 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 (Grandma's 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 or stop for fresh fruit at a roadside stand. 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 your own favorite the local restaurant.

Day 5: Montepulciano

Val d’Orcia, dotted with cypress trees and traversed by the ancient Roman road 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. Important films like the Oscar winners The English Patient, La Vita è Bella and Gladiator were shot here, as well as Zeffirelli’s Romeo and Juliet, and most recently Under the Tuscan Sun, extending Val D’Orcia’s beauty and influence into cinematic history.

Day 6: Cortona

Cortona, Italy is one of the oldest hill towns in Tuscany and is featured in Francis Mayes book "Under the Tuscan Sun". Cortona’s medieval streets are pleasant to wander and you’ll be rewarded with fabulous views of the countryside along the medieval town walls. Cortona has remnants of its pre-Roman Etruscan past, Renaissance artists Luca Signorelli, Fra Angelico, and Baroque artist Pietro di Cortona.

Day 7: Departure

Loop ride around Cortona and transfer back to Florence to conclude our tour.