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Tuscany Off the Beaten Path

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Tuscany is such a renowned destination that it's not so easy to find new things to explore. Here are some original spots all around the region that are worth a visit. Experience a new Tuscany, outside the most famous cities.

Good for
  • Art and Architecture Lover
  • Nature Lover
  • Foodie
  • Peace and Quiet Seeker
  • Like a Local

10 Places

5 City Tips

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Map

10 Places

Historic Centre of the City of Pienza

Historic Sites

Le mura di Lucca

Historic Sites, Points of Interest & Landmarks

Via Francigena

Historic Walking Areas

Strada del Vino Nobile di Montepulciano e dei Sapori della Valdichiana Senese

Wine Tours & Tastings , Food Tours, Walking Tours, Cultural Tours

Osteria Cacio e Pepe

Restaurants

Pitigliano

Destinations

Lucignano

Destinations

Abbazia di San Galgano

Churches & Cathedrals, Sacred & Religious Sites

La Bottega di Volpaia

Restaurants

Orti dei Tolomei

Points of Interest & Landmarks

Marzia T's City Tips

  • During your journey, take a look at the landscape around you and take in the natural beauty of this country.
  • Try to choose restaurants like a local and not like a tourist — you'll avoid higher prices for the same quality. Talk to people and ask for advice.
  • Tips are included in restaurant prices in Italy. However, you can always give the servers a little extra at your discretion.
  • Always wear comfortable shoes: Walking in the historic Tuscan streets can be hard work!
  • To get around Tuscany easily, it is advisable to rent a car.
  • Historic Centre of the City of Pienza
    Historic Sites
    See more photos
    Marzia T Says:

    In the heart of the Val d'Orcia region, you will find the Renaissance city of Pienza, built on orders from Pope Pio II (around 1459). The town is a UNESCO World Heritage site and the area is famous not only for its landscape — an example of Renaissance ideals — but also for the wine and the food, the Pecorino cheese in particular.

    Good for
    • Foodie
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Visit the local producers' little shops and taste the wine and the Pecorino. Is there any better souvenir?
    • The street names are interesting, pay attention!
    Plan to stay:
    2-3 hours
    From the community
    Ranked #127 of 6,261 things to do in Tuscany
    Certificate of Excellence 2014
    • Historic center 08/06/2021
    • Avoid the weekends, but do visit this beautiful town. 10/20/2020
    • Historic Centre of the City of Pienza
    Address:
    near Montepulciano
    Italy
    Other:
  • Le mura di Lucca
    Historic Sites, Points of Interest & Landmarks
    See more photos
    Marzia T Says:

    Entering the city of Lucca through its famous, fortified Roman walls, tourists usually don't pay attention to the park around the area. This is a favorite location for Lucca citizens to have a walk, play sports, or just read a book under the trees.

    Good for
    • Peace and Quiet Seeker
    • Thrifty Traveler
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Nature Lover
    Tips
    • This is the best place for jogging in Lucca.
    • Enjoy the beautiful view of the city.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #2 of 141 things to do in Lucca
    Certificate of Excellence 2014
    • I just love Lucca and this is a must! 09/13/2021
    • Walk around the old city 09/06/2021
    • Le mura di Lucca
    Phone:
    05834422
    Other:
  • Via Francigena
    Historic Walking Areas
    See more photos
    Marzia T Says:

    Via Francigena is an ancient road traditionally walked by pilgrims to reach Rome, and the Tuscan part passes through some amazing areas and cities. One of these is the picturesque town of Siena. Here, Via Francigena runs along the Santa Maria della Scala hospital, which in ancient times offered medical care and hospitality to pilgrims. A different way to experience the region.

    Good for
    • Peace and Quiet Seeker
    • Thrifty Traveler
    • Solo
    • Friends
    • History Buff
    • Couples
    • Family
    • Art and Architecture Lover
    • Nature Lover
    Tips
    • Try to walk even a short distance of Via Francigena — it is a unique experience. In Siena, you can book a guided tour every Sunday morning from June to November.
    • Wear comfortable shoes, of course.
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #1 of 11 things to do in Gallicano nel Lazio
    • Via Francigena, hiking in Italy 12/30/2019
    • A beautiful way to see Tuscany 05/21/2018
    • Via Francigena
  • Strada del Vino Nobile di Montepulciano e dei Sapori della Valdichiana Senese
    Wine Tours & Tastings , Food Tours, Walking Tours, Cultural Tours
    See more photos
    Marzia T Says:

    This wine route is a beautiful walk along the streets of Montepulciano, a little gem of a town with several shops and wine cellars to visit. The perfect occasion to experience where the wine comes from and how it is produced.

    Good for
    • Foodie
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Nature Lover
    Tips
    • The landscape around the village is magical, all vineyards and olive trees covering the hills.
    • Visit the cellars carved in tuff and taste the wine and the typical food of this area for a real Tuscan experience.
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #4 of 25 Tours in Montepulciano
    • A totally practical no nonsense hotel 10/23/2018
    • First stop for planning a tour of the Valdichiana Senese region 08/31/2017
    • Strada del Vino Nobile di Montepulciano e dei Sapori della Valdichiana Senese
    Address:
    Piazza Grande 7
    53045, Montepulciano
    Italy
    Phone:
    +39 0578 717484
    Price range:
    US$67 - US$67
    Hours:
    Mon
    9:30 AM - 7:00 PM
    Fri
    9:30 AM - 7:00 PM
    Sat
    10:00 AM - 6:00 PM
    Other:
  • Osteria Cacio e Pepe
    Restaurants (Italian, Mediterranean, Tuscan, Central-Italian)
    See more photos
    Marzia T Says:

    Not very known among tourists — perhaps because it is situated in a wood, though not far from Siena — this little restaurant offers typical Tuscan food and wine of excellent quality. The staff is friendly and at your disposal for suggestions. A great location to share a good meal in complete peace and quiet.

    Good for
    • Foodie
    • Peace and Quiet Seeker
    • Hidden Gems
    • Like a Local
    • Friends
    • Couples
    • Senior
    Tips
    • Pets are very welcome here.
    • Try Pecorino with honey and pears.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #8 of 37 restaurants in Castelnuovo Berardenga
    Certificate of Excellence 2014
    • Simple food, well prepared 09/22/2021
    • A surprise tip from new friends in Italy 09/21/2020
    • Osteria Cacio e Pepe
    Address:
    Localita Lodoline SNC
    53019, Castelnuovo Berardenga
    Italy
    Phone:
    +39 0577 165 2898
    Hours:
    Tue - Sun
    12:30 PM - 2:30 PM
    7:30 PM - 9:30 PM
    Other:
  • Pitigliano
    Destinations
    See more photos
    Marzia T Says:

    The town of Pitigliano is unfortunately often left out of the conventional tours of Tuscany. Known as 'Little Jerusalem,' it is home to a medieval synagogue that is occasionally in use today, as well as Etruscan tombs, wells, and cellars worth visiting. In the narrow, winding streets of the ghetto near the synagogue, you will find small shops and cozy restaurants.

    Good for
    • Hidden Gems
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Pitigliano, just like Sorano and Sovana, is known as Città del Tufo, a town carved into tuff stone.
    • If you can, visit the Etruscan necropolis along Vie Cave.
    Plan to stay:
    2-3 hours
    • Pitigliano
  • Lucignano
    Destinations
    See more photos
    Marzia T Says:

    Twenty-eight kilometers from Arezzo, in the heart of Valdichiana, the town of Lucignano is famous for the medieval relic 'The Golden Tree' or 'The Tree of Life,' which is on display in the City Museum. A sublime work of goldsmithery, this two-meter high shrine is said to bring luck to lovers. The town of Lucignano itself is constructed as a series of concentric circles forming a distinctive elliptical shape.

    Good for
    • Hidden Gems
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Get lost among the labyrinth of the suggestive alleys of the village.
    Plan to stay:
    2-3 hours
    • Lucignano
  • Abbazia di San Galgano
    Churches & Cathedrals, Sacred & Religious Sites
    See more photos
    Marzia T Says:

    Located about 30 kilometers away from Siena, this old abbey is well worth the journey. Abbazia di San Galgano is a powerful building that has survived the centuries. Its setting in the Tuscan countryside will leave you speechless, while the spiritual atmosphere will inspire you.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • It's a nice walk up to see the sword in the stone, in a chapel five minutes away from the abbey.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #1 of 11 things to do in Chiusdino
    Certificate of Excellence 2014
    • nice pictures 08/07/2021
    • Interesting, we missed the "Excalibur" so we have to go back in the future! 07/12/2020
    • Abbazia di San Galgano
    Address:
    Localita San Galgano
    Palazzetto
    53012, Chiusdino
    Italy
    Phone:
    +39 0577 756738
    Other:
  • La Bottega di Volpaia
    Restaurants (Italian, Mediterranean, Tuscan, Central-Italian)
    See more photos
    Marzia T Says:

    This reasonably priced osteria is found in the charming village of Volpaia, right in the center of the Chianti wine region. La Bottega has a beautiful terrace where you can enjoy delicious Chianti wine and food pairings along with the view from the hilltop.

    Good for
    • Foodie
    • Friends
    • Couples
    • Senior
    • Family
    • Thrifty Traveler
    Tips
    • Definitely order the rabbit and tagliatelle with truffle.
    • Convenient parking just below the restaurant.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #3 of 4 restaurants in Volpaia
    Certificate of Excellence 2014
    • Favorite lunche in a patio in Chianti 10/05/2021
    • Third time visiting for lunch on 3 trips....and we will be back again 10/01/2021
    • La Bottega di Volpaia
    Address:
    Piazza della Torre 1
    Volpaia
    53017 Volpaia, Radda in Chianti
    Italy
    Phone:
    +39 0577 738001
    Price range:
    US$32 - US$42
    Hours:
    Wed - Mon
    12:00 PM - 3:00 PM
    7:00 PM - 10:00 PM
    Other:
  • Orti dei Tolomei
    Points of Interest & Landmarks
    See more photos
    Marzia T Says:

    Orti dei Tolomei is a green area of Siena unknown by most of the tourists. That's why it is the perfect location to have a rest in a peaceful and relaxing atmosphere, with a great panorama of the whole of Siena.

    Good for
    • Peace and Quiet Seeker
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Nature Lover
    Tips
    • Have a stop in this park at sunset — the view is stunning.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #43 of 155 things to do in Siena
    • Small public park on the top of a car park with good views over the countryside to the south of the city. 09/10/2019
    • Different experience in Siena 02/24/2019
    • Orti dei Tolomei
    Address:
    Via Pier Andrea Mattioli
    53100, Siena
    Italy
    Other:
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