A drive through any one of Tuscany’s five major wine regions is about a romantic a day’s outing as you can find. The shapes and colors of the vineyards are spectacular, and views the hills offer are wide and bucolic, the wineries and cellars as varied as can be. The wine regions have been agricultural in one way or another for many centuries so all are filled with old farmhouses, ruins, villas, or country churches. Then there are the castles of the great estates. Almost every noble family’s castle has vineyards attached to it, making for the most wistful images. Most of them have wine tastings, so don’t be put off that it is not loudly advertised—this is Tuscany, all you might see is a small hand-painted sign saying ‘Cantina’ which means cellar. A word about visitor courtesy. A vast number of the wineries are small and family-run, meaning their time is precious and they have little wine. They make their daily bread from selling wine, so if you intend to buy, great, by all means stop and visit. If not, drive on. The drives themselves vary greatly from the gentle hills around Montalcino, to the twists and turns of Chianti, to the plains of the Marrema. What is consistent in all five itineraries I laid out, is the beauty of villages and hamlets along the way so do take time to stop and visit even just for a short walk and an espresso or a gelato. And, of course, a glass of local wine.
This is the land of one-hill views, meaning the hilly terrain lets you see only the hill before you. Wonderful for gazing close up at vineyards, ruins, and castles. The best base is Greve, close to Florence. Wind south to Panzano, then through Castellina towards Poggibonsi. Go slow, this is beautiful especially in the autumn light. Do have lunch at Alcide, a non-descript hotel and restaurant that makes a wonderful Livornese fish soup called cacciuco. From Poggibonsi take a back road south to Colle di Val d’Elsa then on to Monteriggioni. Pass Siena (save it for another day because there is way too much to see) then take a back road to Castelnuovo Berardenga, north to Gaiole, then Radda, then back to Greve.
This is a country of wide, low hills and long, beautiful views. From our house, we see eleven layers of hills misting toward the sea. The region alternates wonderfully between woods, vineyards, wheat fields, and olive groves. Jewel-like hamlets and villages dot the landscape. From Montalcino descend to Buonconvento, a charming, friendly walled town rare in that it’s in a valley. Drive through Torrenieri, loop back up through Montalcino to Castelnuovo dell’Abate. Here, the magnificent travertine church Abbazia di Sant’Antimo is a must. Take a slow, dirt road to Sant’Angelo in Colle (stunning views and have lunch at Il Leccio. Or Il Pozzo). Descend through Sant’Angelo Scalo (don’t even slow down) then up to Castello Banfi. Take a dirt road through Tavernelle to tiny hamlet of Camigliano. Backtrack to Montalcino. A long day but you’ll see much on the way.
Montepulciano / Vino Orcia
Vino Nobile di Montepulciano is one of Tuscany’s oldest wines dating back centuries. Vino Orcia is a fledgling appellation with interesting blends but mostly breathtaking scenery. They are adjoining zones with many small and medium-sized wineries so be prepared to sip a lot. From Montepulciano head west (slowly) to Pienza. This spectacular town is a must stop, as is San Quirico. Have lunch at Osena with homemade pastas by my dearest friend Rosanna. From there, head south to Bagno Vignoni, another must, then up to Rocca D’Orcia. Make sure you’re dead sober before you climb to the top of the watchtower. From here east to Montechiello. The view from here in the late afternoon is the stuff of dreams. Back to Montepulciano, up a serpentine road that seems right out of a James Bond movie. This will be a day you won’t forget.
Scansano / Argentario
A long but unforgettable day involving wild, empty mountain roads where Morellino di Scansano is made, then coastal cliff hangers where you can taste the yellow, fruity Ansonica. The trip can be halved by staying overnight in Argentario, the dramatic promontory jutting into the sea. Start from Cinigiano to Talamone on the sea. This little-known fishing port has dramatic views and good seafood at Il Buco. Head down to the fishing town of Porto Santo Steffano then west out to a private cape, Capo D’Uomo. It has amazing cliff-hanging vineyards worked by hand and the most beautiful small winery. Return through Orbetello, through Magliano, Scansano, to Cinigiano.
Bolgheri/ San Gimignano
This is as different from the rest of Tuscany as can be. Start from the many-towered town of San Gimignano (it had fifty-two towers in its twelfth-century heyday, riches mostly gained from cultivating saffron). To me, what is more impressive are its many small piazzas, and its pale Vernaccia wine. Head to Volterra, one of the most important sites of the Etruscans, then southwest down to the Bolgheri region. This is the home of remarkable blends like Sassicaia and Ornellaia. Lunch on the seashore at La Pineta, (hidden in the pines at Marina Di Bibbona). Such a lunch merits a restful afternoon; best to stay in the area overnight. Head back east through Massa Marittima on the road of your choice. All roads here are wonderful for wandering.