Three of my Favorite Tuscan Towns for Day Trips

Last fall I spent a week roaming around Tuscany, scouting out hotels and the best Tuscan towns for day trips. Long before Frances Mayes inspired millions with her novel, Under the Tuscan Sun, I have dreamt of living in Italy. Now I enjoy helping families make their dreams of a Tuscan vacation come true through my trip planning services.

Of course, what you do while you are in Tuscany depends a lot on where you stay. After all, you don’t want to spend four hours in the car just to visit yet another Tuscan hill town. If you are really into wine and are looking for that classic Tuscan landscape, then the Val d’Orcia area in Southern Tuscany might be a good fit. If you want some time at the seaside or to do a day trip up to the Cinque Terre, then the area around Lucca, Pisa or Forte di Marmi would be a good fit. And if you are planning on spending a day or more in Florence, then Central Tuscany is the place to be. 

Wherever you make your home base, you can’t visit Tuscany without taking some day trips around the area. Don’t plan on visiting a different town every day, or you will just get hill town fatigue. You will likely want to visit some of the most popular towns like Siena, Lucca, maybe Pisa and, of course, Florence. But if you want to avoid the crowds, be sure to also check out some of these little gems.

Best Tuscan Towns

San GimignanoSan Gimignano best Tuscan towns

About an hour from both Florence and Siena in Central Tuscany, the little town of San Gimignano is certainly not “undiscovered,” but it isn’t overrun with tourists either. Like many of the Tuscan towns, you need to park outside of the city walls in one of the paid public lots, so it pays to get there early. Also, bring along some coins for the parking meter machine.San Gimignano tower

There are a couple of museums in town, but the main attraction is Torre Grossa, the Great Tower, in Piazza del Duomo. The tower is 54 meters high and you can buy a ticket to climb to the top. Some of the steps are metal grate so if you are acrophobic, it may not be for you. Just keep in mind that you shouldn’t  wear a dress if you are climbing the tower because the last section is a straight up ladder into the belfry while the person behind you waits below. The views from the top are absolutely amazing and well worth the climb!

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After a visit, stop by the nearby Fattoria Poggio Alloro agriturismo for lunch (reservations included), wine tasting and cooking classes.Fattoria Poggio Alloro wine barrels

Pienza

About 20 to 25 minutes from both Montalcino and Montepulciano, respectively, in the picturesque Val d’Orcia region of Southern Tuscany, Pienza sits perched on a hilltop overlooking the beautiful views below. It is one of those adorable towns where every alley leads to stunning views over the walls.Pienza wall

It won’t take long to explore the cathedral and piazzas, but you will want to leave time for some pecorino tasting. You will find many shops offering cheese tastings, and the restaurants will serve up their famous pici con cacio e pepe (one of my favorite dishes.) If you are looking for a lunch spot, try the hip La Bandita Townhouse.

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Also check out the Palazzo Piccolomini, which was the residence of Pio II (who went on to become Pope), and offers up formal Italian gardens.

Volterra

An hour from Siena and a little over an hour to Florence, Volterra may be best known for its role in the Twilight Series. (It was the Ancient Italian city where the Volturi live.) While that may be enough to attract some tourists, the town is not at all crowded and is a great spot for finding a true authentic experience.Volterra walls

The ancient walls date back to Etruscan and Middle Ages, and the Palazzo dei Priori has the feel of a medieval castle. Some of the sights to see include the Duomo, Etruscan Museum, and Roman ruins and Amphitheater. But really it is another town where just wandering around is part of the fun (and be sure to check out the great leather goods shops too!)

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What do you think are the best Tuscan towns?

Plan this trip!

  • This hotel makes a great home base for visiting San Gimignano or Volterra with truly authentic, luxury accommodations and five-star amenities and service at a four-star price. Check prices and review. 
  • If you want to stay in Southern Tuscany, this agriturismo is perfect for a romantic getaway, and this one offers apartments that are perfect for families.
  • Keep in mind that most agriturismos and villa rentals require a Saturday to Saturday stay.
  • Be sure to purchase a paper map and get printed directions to your destination as Google Maps isn’t entirely reliable in Tuscany.
  • Check out my tips for what to do in Florence
  • Need help planning your trip? Check out my trip planning services.

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Tuscany travel tips: Best Tuscan towns for day trips from Florence and Rome

2 Comments on “Three of my Favorite Tuscan Towns for Day Trips

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  1. Love the pictures! Brings back fond memories of strolling through san gimignano over 20 years ago. hoping to get back one of these days and rent a villa.

      It is definitely the place to go back to again and again!

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