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3 Day Itinerary in Tuscany for Wine Lovers

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

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