Tuecany/Umbria Self-Guided Tour

Springtime in Tuscany

Everything about Tuscany envelops the senses. The countryside is blanketed by bountiful vineyards, olive groves, sunflowers, and dense chestnut groves, providing a checkerboard of visual contrast. Groves of cypress trees pierce the sky, separating green and golden plots of land. Etruscan civilization and ancient Roman roads greet you along every route. Dreamy ancient medieval villages perch on hilltops, periodically punctuating the landscape.

A description of Tuscany would be incomplete without mentioning the rich palette of flavorful dishes, which marry perfectly with the local wines. Savory bruschetta, tortellini ai funghi, ribollita, crostini, tiramisu – almost as enchanting to say as they are to eat! Cooking is an art in Tuscany, and you even have an option to attend cooking classes. Tuscany is a wine lover’s paradise as well, with some of the world’s most famous wines produced in this region, including Chianti, Brunello and Orvieto Classico.

In just about every village you will have the opportunity to engage in one of the world’s greatest pleasures - people watching while enjoying cappuccino and pastries in an outdoor café nestled in a medieval piazza. Tuscany is truly La Dolce Vita!

Your Tuscany adventure can also be combined with Umbria, so close but so different in characteristic. Possible additional activities include cooking classes, horseback riding, hiking, as well as guided visits to ancient villages and cathedrals and special tastings at wineries and olive oil producers.

Hub A - Florence to Siena

Principle Villages: Castellina in Chianti, Radda in Chianti, Gaiole, Greve, Siena, Asciano, Colle Val d'Elsa, San Gimigniano, Volterra.

San Gimigniano - one of Tuscany's
most beautiful villages.

Cycling: moderate to challenging. Very little in this fascinating region is flat! Nevertheless, most Spokes have options to shorten the route, so even though there may be hills, the total mileage can be quite low if desired.

Hub B - Quintessential Tuscany: Cortona to Val d'Orcia

Principle villages: Montepulciano, Pienza, Montalcino, San Quirico d'Orcia, Castiglione d'Orcia, Chiusi, Cetona, Sarteano, Cortona and the Lago di Trasimeno.

I call this road on the Crete Senese the "Zen of Cycling".

Highlights: The Crete Senese, the barren chalk cliffs south of Siena. Italy's center of gastronomic products. Black cypress trees reaching towards the heavens, Brunello, Italy's most famous wine, medieval piazzas for the best people watching.

Cycling: three of the Spokes in this region are moderate to more challenging, with little opportunity to shorten them as they wind through the hills of the Val d'Orcia. But on the eastern edge of this region, there are several easier Spokes (though one includes a generous climb up to Cortona). In fact, one Spoke, around Lago di Trasimeno, is one of the flattest segments in this part of Italy - less than one mile of climbing in 34 miles!