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While wandering the cobblestone streets of various tiny hill towns, the unvarnished identity of Tuscany is vibrantly apparent and accessible. A traveler inevitably witnesses small moments of real life. Catching snippets of conversation between elderly matriarchs, passing families at the market, stumbling upon local celebrations, one feels like a welcomed observer in the home of a boisterous extended family.

True to a fault in tradition, festival, and stubborn custom, Tuscany’s charm comes from the way life unfolds around, and very nearly without regard to, the international observer. The same proud antiquity and rustic authenticity so apparent throughout Tuscan culture is equally evident in the various world-renowned wines of the region.

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Rent A Car

The general laissez-faire public transportation of Tuscany makes renting a car a necessity. Preserving the autonomy to venture down whichever back road seems most alluring will make all the difference.

Leave Some Things to Chance

Tuscany is replete with hidden gems—too many to be listed here. The following itineraries will work best if you combine them with the appropriate (for you) amount of spontaneity. Remember, whenever the urge strikes, wander, linger, explore, and engage!

At the Same Time, Call Ahead!

Be sure to call ahead and make an appointment, reservation, etc. for the various tastings you plan. This isn’t always a necessity, but plain courtesy makes it a must, and the hard-working winery owners will certainly thank you for the heads up with an extra pour or two. You can make these arrangements from your temporary Tuscan residence; your hotel or hostel can help!

Buon Giorno!

A little language skill goes a long way, so make some time for practice! I recommend DuoLingo or your local community college. It’s never too late. Italy isn’t France, and a poor attempt will go over better than no attempt.

Siena is at the heart of Tuscany, and the perfect place to return to at the end of each day. Here are some day trips from Siena, fanning out along the points of the compass:

Siena, Tuscany, Italy
Panoramic view of the historic city of Siena. Tuscany, Italy


South of Siena lie the Crete Senesi (Sienese Clay), a landscape so brilliantly sculpted that some deity or another must have been involved. The tight curves, crested knolls, and rolling hills of this farmland are a joy to see and to drive (or bike!). From Siena, follow road signs for Taverne d’Arbia—Asciano—Montalcino. Of course the ultimate destinations to the south are the wine powerhouses of Montalcino and Montepulciano, both gorgeous hill towns famous primarily for their sangiovese grape production and the associated wines: Brunello di Montalcino, Rosso di Montalcino, and Vino Nobile di Montepulciano. Among the more than 200 certified Brunello producers, you won’t be disappointed by a tasting at La Fonterenza, Podere Le Ripi, San Polino, La Rasina, or Piombaia, all small-scale Brunello producers whose passion and experience are expressed in their wine. From Montepulciano, I recommend Avignonesi, Croce di Febo, and Il Conventino. Be sure to visit the churches in each town, and make time for a cappuccino if its morning or a simple caffe in the afternoon.

Additional Recommendations

Towns: Castiglione d’Orcia; Roca d’Orcia; Bagno Vignone; Pienza
Restaurants: Il Moro; Cisterna Nel Borgo; Pasticceria Artigianale Scheggi; Locanda Paradiso (because this tiny hill town might fall off the cliff in a few years!)
Random: Il Bosco Della Ragnaia Woodland Sculpture Park


San Gimignano wine in the heart of Tuscany 1
San Gimignano

In the westerly direction we find the Super Tuscan reds and the many-towered hill town of San Gimignano. Outstanding wine tasting can be had at San Quirico, Poggio Alloro, Massa-Vecchia, and La Canneta. While famous for their white varietal, vernaccia, each of these farms offers a powerhouse of Super Tuscan reds; and be sure to taste their vin santo as well. A dessert wine, vin santo is made by hanging white grapes until they lose enough water to sufficiently raise their sugar content. The wine is higher in alcohol yet with residual sugar to compensate. In addition to world-class wine, Tuscany produces some of the best pork in the world. The prosciutto of the medieval Cinta Senesi pig rivals the best Jamón Iberico (and certainly Prosciutto di Parma). These pigs are still raised on vast tracts of predominantly oak and chestnut forest. A visitor would be remiss to not include a salumi tasting and farm tour at Tenuta di Spannocchia, a leading producer of Cinta salumi with their own on-farm butchery. Those willing to do a bit of sweet talking (and perhaps willing to join the nonprofit Spannocchia Foundation as members) may also be able to line up a wine and/or olive oil tasting as well. Don’t shrug your shoulders at the olive oil tasting; I often plan my trips to Tuscany for November despite the suboptimal weather simply to coincide with the season of olio nuovo, the freshly pressed, greenest, spiciest olive oil, and one of the great culinary wonders of the world.

Additional Recommendations

Towns: Volterra; Radicondoli; Belforte; Monteriggioni
Restaurants: Ristorante Sbarbacipolla; Trattoria-Pizzeria La Pergola; Ristorante La Compagnia; Ristorante La Bottega di Stigliano; Ristorante Da Beppino; Enoteca Da Gustavo Di Becucci Maristella
Random: Abbazia di San Galgano (roofless, deconsecrated Abbey of Sir Galahad complete with sword in stone); The Castle that God Only Knows (purchase some cheese, salumi, and wine from Tenuta di Spannocchia for a picnic hike)


I vigneti del Chianti - Toscana wine in the heart of Tuscany 1
I vigneti del Chianti – Toscana

To our North we find the famous region of Chianti, where, again, a world-renowned, sangiovese-based red wine is born. Like Brunello and many other wine classifications, Chianti is strictly controlled for consistency and quality. The region, like the others, is dotted with stone hill towns, luscious valleys, and fertile farmland. Top wineries on my list are Poggerino, Vignavecchia, and Vallone di Cecione. While in the region, you won’t want to miss the amazing heritage beef served up by ACDC-loving butcher Dario Cecini in Panzano, an excellent stop for lunch and a brief stroll to the simple yet stunning church in between wine tastings.

Additional Recommendations

Towns: Radda in Chianti; Greve in Chianti; Castellina in Chianti; Gaiole in Chianti; Barbischio
Restaurants: Antica Macelleria Cecchini; Castello di Verrazzano (call ahead for tasting, tour and lunch); Ristoro di Lamole (for a sunset dinner)
Random: The Ruins of Montegrossi Castle; Pastificio Artigiano Fabbri (for a artisanal pasta factory tour)

And if you’re looking for places to enjoy from your Siena homebase, keep food and wine at the top of your activities list:

Wine party wine in the heart of Tuscany 1
Red wine with charcuterie assortment

Bar Pasticceria Nannini for cappuccino and a brioche (you have to pay first, then present your receipt) to really feel local, order “un capuccio (ha-POO-cho), é un bell brioche.” You’ll probably get an eye roll, but good effort! Or skip breakfast; most Italians seem to.


Consorzio Agrario, grab a number and get some freshly baked pizza and flatbread. Also your source for picnic fixings: cured meat, cheese, bread, cookies, fruit, etc.

Da Trombiche, authentically rustic, typical Tuscan cuisine in an unassuming atmosphere.


Taverna San Giuseppe, did someone say Michelin Star? Be sure to make a reservation well in advance!

Highlights:  Grab that snack basket and a bottle of wine (don’t forget a corkscrew) and head to the campo for some great people watching (free water from the public fountain). At various times throughout the year, the campo hosts the Christmas Market (usually the second weekend in December); the famous horse race, and among the most fascinating of sporting events, il Palio, which happens twice during the summer. Don’t forget to look out for the 17 contrade (neighborhood) churches and, of course, the Duomo and Siena town hall.

For tips on wine tasting, click here
For more travel guides, check out our guide to cruising, Cambodia, and Japan

Tuscany, Crete Senesi rural landscape on sunset, Italy. Lake and
Tuscany, Crete Senesi near Siena, Italy
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