Maybe it’s the wine, maybe the food, the atmosphere, the people, the scenery, the medieval towns and villas, or maybe it’s a combination of all of them. But whatever it is, we love Tuscany.

Any trip to Tuscan must include at least some of its larger cities. Florence is truly one of the world’s “must-see” cities. Its history, its art, its architecture and its atmosphere absolutely must be experienced. We begin and/or end every Tuscan trip in Florence and will continue to do so. Siena, Florence’s millennia-old regional rival, is almost as beautiful and someday, we will return specifically for the Palio de Siena horse race and celebration. Pisa, meanwhile, should be seen at least for its iconic tower and its cathedral.

Tuscany, however, is far more than its major cities. UNESCO, for example, has designated six Tuscan towns and areas (spread all across the state), as World Heritage Sites (the historical centers of Florence, Siena, Pisa, San Gimignano and Pienza, and the Val d’Orcia countryside). And this does not even include such other must-visit places as Lucca, Greve, Montepulciano and Montalcino. Much of the real Tuscan charm lies in these and many other small towns—especially in a number of its walled, medieval hilltop towns—and in its rural countryside. And this is not to speak of the joys of experiencing its broad array of foods, wines and the hospitality of its people.

So, when we go to Tuscany, we spend most of our time in these towns and in the countryside.

Navigating a Tuscan Adventure

But which town and which countryside, and how do you organize and navigate a trip that will allow you to see and do as much as possible, with as little stress as possible. After all, Tuscany covers 9,000 square miles, separated by mountains and endless hills and connected primarily by small, winding, local roads that are rarely identified by names or route numbers.

Driving speeds, except on the limited number of expressways, can be slow and many of the most interesting towns always seem to require long drives—typically 60-90 minutes each way. And then there was our Android phone’s GPS, which seemed to lose satellite coverage every time we most needed it. The result, every drive required close tracking on maps and both of us watching for and trying to interpret every road sign. This, combined with the frustratingly inconsistent signage required us to add about 30 minutes include “getting lost” time into every trip calculation. Worse still, since we were unable to count on our GPS, we had to map out and plan every trip in advance and follow each turn on our map. And this was in addition to both of us having to watch for, read and determine how to interpret every direction sign—at least when we could find them. Given all of this, driving can become a chore.

But, for all our driving challenges, it is more than worth it. Many of the roads are beautiful: Hills looking down into valleys and over the next ridge lines. Towns and villas with red tile roofs and the occasional hill town on the horizon—and vineyards everywhere. And it is all even more lovely in the morning fog.

Then there are the stops and the experiences. Exploring the wonderful towns, exploring the shops, tasting the wines, cheeses and salumis, eating at as many restaurants as possible and then working the calories off by walking the hill towns, hiking the forests and biking the scenic back roads. Then there are the culinary and wine adventures such as foraging local produce markets, attending cooking schools, hunting truffles, tasting wines and cooking your own meals. (More on these experiences in following blogs.) And then there are the people: wonderfully friendly and amazingly patient with visitors who do not speak the language.

So, unless you plan to spend your trip in one location, and miss most of these experiences, you may want to resist the urge to find one perfect villa or hotel room and organize all side trips from there. In the end, you will be able to reduce the chore of driving and experience much more of Tuscany by dividing your trip into segments. So, after leaving Florence, you can stay in:

• Greve, to explore for northern Chianti;
• Siena, to experience that city, to explore wonderful neighboring towns as Monteriggioni, Volterra, San Gimignano, Certaldo and surrounding areas;
• Montepulciano for the town itself, its Vino Nobile de Montepulciano wineries, and for neighboring towns including Montalcino (and its Barolo wineries), Cortona, San Giovanni d’Asso (for truffle foraging) and for brief explorations of Western Umbria (Lago Trasimeno and Perugia;
• Lucca for that town, for the primary sights of Pisa and as a launching pad for a side trip into southwestern Liguria and the lovely towns of Cinque Terra (see our following blog).

We discuss these and other of our favorite Tuscan towns in our following blog.