Tuscany is such an extraordinary part of Italy.  I love visiting Florence and Siena and soaking in the history, art and architecture that escape from every brick and cobblestone.  But my favorite way to explore the Tuscan region is to spend several days in its beautiful, iconic countryside.  At a gentle pace, it is possible to stroll through hill towns and taste the beautiful wines that are some of the best in the world.  A 3-day itinerary in Tuscany for those who love wine is pure joy.

After the hustle and bustle of the beautiful Italian cities, you may wonder what to do with 3 days in the countryside. Let us plan it all for you!  Contact us to put together your own custom itinerary.  We would love to create a unique vacation plan just for you, or book the one described below for your small group.

Beautiful Toscana Wine

Certainly, Chianti is a famous and important Tuscan red wine, but I want to concentrate on the part of Tuscany’s wine region that produces Brunello and Vino Nobile di Montepulciano.  This slice of Tuscany is enchanting and in order to really get into the rhythm of the place and enjoy its unique food and wine, you need several days.  You also will likely need to have a car, especially if you want to visit some of the wineries.  Or you can book a driver or a driver/guide to take you from place to place. There is a lot to see – and taste!  You can read about the specific characteristics of these two wines in our blog Comparing Brunello and Vino Nobile Wines.  If you would like to experience the differences for yourself, spend several days in the area, and then plan to return.

Where to Stay to Taste Famous Tuscan Wine

I like to stay in one place for several nights so that I only have to unpack once.  If you look at a Tuscany Wine Map you’ll see that the lovely village of Pienza, famous for its pecorino cheese, is in between Montalcino to the west and Montepulciano to the east.  Pienza and its surrounding area is a lovely place to settle in for a few days.  If you remember the movie, The English Patient, or even’t the 1960’s version of Romeo & Juliet, you may already know Pienza, as this is where parts of these movies were filmed.

Choose a farmhouse or agriturismo or even stay at a winery to really get the flavor of the place.  Palazzo Massaini is an example.  This winery has several farmhouses where you can stay and enjoy an extraordinary view.  Then, take day trips, being careful to have a designated driver or a slow enough pace to allow you to negotiate the winding roads and rolling hills on the way home.  You could locate in Montalcino or in Montepulciano but I like Pienza because it’s in the middle.  Oh, and it’s also beautiful, with spectacular views of the Val d’Orcia. 

On your first night, ask your hosts for dinner recommendations for the last night of your stay.  Let them know if you would like an upscale restaurant or a spot where the locals dine regularly.  Share how far you are willing to drive and ask them to call and make a reservation for you. They will most likely be happy to suggest their very favorite places and help you decide where to dine on your last evening in Tuscany.

Day 1 - Explore Montepulciano and Montichiello

The town of Montepulciano is incredible for those who enjoy exploring all that Tuscan hill towns have to offer.  If you enter the town from the main gate at the bottom of the village, know that you will have a steep climb to get to the top.  Along the way, you will pass cellars and wine bars where you can taste this famous wine.  Montepulciano is littered with spots to try Vino Nobile di Montepulciano, which is made from the same grape as Brunello, but is somewhat less complex, with a little more finesse.

We really enjoy La Vineria di Montepulciano for a great selection from different makers, accompanied by beautiful charcuterie boards with local cheeses and dried meats.  One winery you can visit within Montepulciano’s historic walls is Talosa, whose historic cellar dates from 1500.  It is located under Piazza Grande and if you don’t want to be on any sort of schedule, you can simply visit their wine shop.  If, however, you’d like to have a tour and tasting, it is easily arranged, by appointment.  Be sure to call ahead and ask for a time when an English-speaking guide will be available.

On the way back to your home base of Pienza, stop by Montichiello and wander through the narrow alleys of this tiny hill town.  If your timing is right, you can enjoy a glass of wine al fresco while enjoying the sunset.  Then, enjoy dinner at Ristorante Daria and enjoy a selection personally selected for you from her cellar.

Day 2 -Tour of Tuscany in and around Pienza

On this day, there will be plenty to do in and around your home base. If you happen to be staying at a winery, ask to have a tour in the morning before you embark on the rest of your day.  Be sure to ask them questions about the area, and discover their personal story.  Learning about the winemakers themselves makes what you taste in the bottle all that more memorable.  Take the time to connect with some of the people who make Tuscany so special.

Spend part of your day strolling through the beautiful town of Pienza and be sure to stop inside some of the cheese shops and taste the local pecorino (sheep’s milk) cheese that is so important in this area.  Taste the different kinds – pecorino fresca, aged pecorino, pecorino with grape must, pecorino with red peppers, pecorino with truffles…. you get the idea.  Each one is delicious and unique.

Book a tasting at Enoteca di Ghino in Pienza and you will not be disappointed.  Here you will find wine from some of the best producers from some of the best vintages.  This enoteca also has wine from other parts of the world, but you are in Tuscany, Italy, so I recommend concentrating on the wines from this region.  But here you will find wine from some producers that make beautiful Italian wine from Tuscany, outside of Montalcino and Montepulciano.  For example, try Sassicaia from Bolgheri.  This region is still in Tuscany, but farther west. This Super Tuscan is a Bordeaux-style blend so it will be different than the 100% Sangiovese wines of Brunello and Vino Nobile.  Enjoy the many nuances of these different and spectacular wines.

After your tasting, why not pop in to several of the small shops and pick up some of the lovely cheese you tasted earlier, along with some spectacular charcuterie?  Select some homemade bread as well, remembering that Tuscan bread is unsalted. Historically, salt was expensive and Tuscany was a poor part of the world.  Those living there couldn’t afford salt for their bread.

Choose a nice wine to accompany your picnic and ask the vendor to uncork the bottle for you.  Request some plastic cups or maybe you can borrow some nicer ones – just be sure to return them when you’re done.  Take your fabulous meal to the edge of the city and find a bench or a low wall where you can relax and soak in the incredible views of the Val D’Orcia while you enjoy your picnic.

After lunch, visit a sheep farm where they make pecorino cheese. Podere il Casale offers a remarkable visit. It is not easy to find, but it provides a spectacular setting once you get there.  You could enjoy a tour (by appointment) or even take a cooking class with Sandra.  She and her husband are Swiss but they moved to Tuscany before there were very many visitors and they have made this beautiful land their home.

Alternatively, drive south to Bagno Vignoni and visit this ancient town that was likely known even in Etruscan times.  See the steam from the thermal waters drifting up toward the sky before their crescendo down the cliff.  Peek into the ruins of Roman baths and see where pilgrims stopped for rest while traveling along the Via Francigena, the ancient road that led from France to Rome.  You may want to spend some time soaking in the hot spring fed pools and relaxing in a Roman Sauna at the Albergo Le Terme Spa.

You may enjoy dinner in Bagno Vignoni at Osteria del Leone or head back to Pienza and duck into Latte di Luna, a traditional trattoria with local dishes such as handmade pici pasta, roast suckling pig, and duck with black olives.  This can be accompanied by a lovely bottle of wine from the Val d’Orcia.  You just drove through the vineyards that produce the grapes for what’s in your glass.  Be sure to leave room for some simifreddo alla nocciola (hazelnut ice-cream) for dessert.  In the summertime, you can dine al fresco in the piazza in front of the restaurant, shaded by large umbrellas.  You will want to book ahead, even if it’s not the high season, and note that Latte di Luna is closed on Tuesdays.

Day 3 - Enjoy some of Italy’s most prestigious wines from Montalcino

Today, take a leisurely drive west over the undulating hills of Tuscany and spend time in beautiful Montalcino.  Parking can be tricky, especially in the summertime.  Your best bet is to park near the Fortress at the top of town.  Walk inside the ancient defensive walls and visit the Enoteca la Fortezza inside.  Here, you can taste several Brunellos and compare the difference between traditional producers and those who use more modern techniques.  The staff speak good English and will answer your questions and offer advice.  From inside the enoteca, ask for permission to go upstairs which provides access to the wall walk where you can see vineyards in every direction.  Some sommeliers can tell you which side of the hill your wine came from by the aromas and taste in the glass. 

Take your time exploring the nooks and crannies of Montalcino.  Visit the wine shops and ask lots of questions.  Admire the coats of arms that adorn the Palazzo dei Priori, built in the early 14th century.  When your legs get tired, have lunch at Re di Macchia and try the pici pasta with ragu, or the nettle pesto and porcini ravioli.  Or, return to the enoteca in the Fortress for a nice lunch.  You can either enjoy your meal inside, surrounded by hundreds of wine bottles, or dine outside in the sun, within the castle walls.

After lunch, visit one of the beautiful Brunello producers for a tour and a tasting.  You’ll want to make an appointment to ensure availability and an English-speaking guide.  Getting to know more about a specific wine – how it is produced and the family who makes it – is an amazing experience, and part of why you visit Tuscany’s wine region.  If it’s a wine that is imported to your home country, every time you see a bottle made by that producer at your favorite wine shop, you will remember setting foot in the vineyard where the grapes grow to make that wine.

Two producers that offer wonderful English tours are Banfi and Altesino.  These vintners make excellent wine that is exported to North America, so you’ll be able to find their wine at home.  They both offer visitors a chance to tour their facilities and taste a variety of their wines in a spectacular setting.  Alternatively, request a recommendation for a smaller producer from one of the wine shops in Montalcino.  If you ask them, they may even set up an appointment for you.

Enjoy the dinner arranged by your lodging hosts on the night you arrived.  As they live in the region, they are a wonderful resource and often know the very best choices for their guests.  Put yourself in their hands and trust their recommendations.  In the morning when you have to depart, let them know about your favorite dishes and the wine you shared the night before.

This 3 Day tour of Tuscany for wine lovers is just enough to whet your appetite.  If you’re anything like us, you’ll want to return again and again.

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Betsy Ball – Betsy is co-founder and partner of Euro Travel Coach (ETC), which crafts custom European vacations for independent travelers and leads small group trips to Europe. She is a passionate and culturally curious traveler who thoroughly enjoys sharing her love for exploring Europe with ETC clients. Prior to founding ETC, Betsy taught International Business at Tarleton State University in Texas (part of the A & M System) where she led study abroad trips to multiple European countries and other worldwide destinations. She retired from teaching in 2017 and since then, Betsy and her husband, Co-founder and Partner, Greg, have been traveling through Europe multiple times per year for as many as 9 months at a time. She has a degree in hotel, restaurant management from Michigan State University and an MBA from Southern Methodist University in Dallas. She also holds a Level 3 certification from the Wine & Spirits Education Trust.