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San Gimignano

Top 6 Caves around San Gimignano

Best caves around San Gimignano include historical underground structures and natural formations within the broader Tuscan landscape. This region, known for its medieval towers and rich history, offers insights into ancient civilizations and winemaking traditions. Exploring these sites provides a different perspective on San Gimignano's heritage and natural beauty.

Best caves around San Gimignano

  • The most popular caves is Maurizio's Caves in Gambassi Terme, a cave where a hermit once lived. These caves feature figures chiseled into the stone and are part of an excursion that combines natural phenomena with the beauty of the Tuscan landscape.
  • Another must-see spot is Bear's Cave, a natural monument. Legend states that a bear once inhabited this cave, adding a unique historical element to its natural formation.
  • Visitors also love Necropoli del Portone Etruscan Tomb, a historical site. This necropolis features hypogeum tombs from the 3rd-1st century BC, offering a direct connection to Etruscan civilization and funerary rites.
  • San Gimignano is known for its historical underground structures, natural caves, and ancient burial sites. The area offers a variety of underground experiences, from Etruscan tombs to natural formations and hermit dwellings.
  • The caves around San Gimignano are appreciated by the komoot community, with 25 photos shared and 24 upvotes across the highlights.

Last updated: June 2, 2026

Necropoli del Portone Etruscan Tomb

Highlight • Historical Site

In this necropolis there are two hypogeum tombs from the III-I century BC. belonged (maybe) to the Gens Calcina.

The Etruscan Volterra had probably already been conquered by Rome (298 BC), but its civilization and rites were still (and for a long time) around.

The graves were likely found in 1880, but the date is not certain.

The second grave also descends deep into the ground with a double staircase (dromos) ... certainly only partially original. If you go down the stairs, you come to a large, square anteroom from which four (small) burial chambers lead, each with docks for storing urns.

(Parking is not possible here, you should come on foot)

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Castelvecchio Farmhouse and Cave

Highlight • Settlement

Set in a dense forest on the outskirts of San Gimignano, in a timeless location, lies the Tenuta di Castelvecchio, behind the nature reserve of the same name, where the ruins of a once flourishing medieval town can be admired. The village, already inhabited in Etruscan times, reveals all the wild and mysterious charm that characterizes the entire nature reserve. The property allows you to enjoy the intense and absolutely unique atmosphere of the place without sacrificing the most modern comforts, very close to the most important centers of artistic and cultural interest in Tuscany and, therefore, the world.

Contact:
Località San Donato 13, 53037 San Gimignano SI, Italy
+39 3316203384
+39 3924620949
info@tenutadicastelvecchio.it

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Maurizio used to live here as a hermit and chiseled a few figures into the stone. Ropes help to get safely down in wet weather.

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Bear's Cave

Highlight • Cave

Legend says that this was the cave where a bear lived..

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Hidden River Trail and Sulphur Geyser

Highlight (Segment) • Trail

The trail is visible on the map until the geysir. Then just follow the river when dry. Later you will see a path that is marked aside the river. It is a nice hidden valley and it ends at a cave with waterfall dependant on water level. Nice shadow on hot tuscany summer days - and a bit of adventure.

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Tips from the Community

Fabio
July 12, 2025, Castelvecchio Farmhouse and Cave

a very beautiful place where you can refresh yourself in the vast forest of the municipality from which the path to Castelvecchio starts.

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Set in a dense forest on the outskirts of San Gimignano, in a timeless location, lies the Tenuta di Castelvecchio, behind the nature reserve of the same name, where the ruins of a once flourishing medieval town can be admired. The village, already inhabited in Etruscan times, reveals all the wild and mysterious charm that characterizes the entire nature reserve. The property allows you to enjoy the intense and absolutely unique atmosphere of the place without sacrificing the most modern comforts, very close to the most important centers of artistic and cultural interest in Tuscany and, therefore, the world. Contact: Località San Donato 13, 53037 San Gimignano SI, Italy +39 3316203384 +39 3924620949 info@tenutadicastelvecchio.it

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Johann
October 7, 2024, Grotta dell'Orso

Looks almost like the dressing room 🤣

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the beauty of the Tuscan landscape together with the natural phenomena of the sulphurous spas with spontaneous springs in the woods, the Mediterranean scrub, the cave where Maurizio spent 13 years of his life as a hermit at the beginning of the 1900s, make this ring an interesting, beautiful and feasible excursion from everyone

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There are scorpions here! A real crypt, but it is illuminated. Located about 100m from the main street.

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Ivan Lucini
November 16, 2022, Grotta dell'Orso

Legend says that this was the cave where a bear lived..

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Alex
July 27, 2022, Grotta dell'Orso

Swimming pool

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Completely without water in August

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Frequently Asked Questions

What historical underground sites can I explore near San Gimignano?

You can visit the Necropoli del Portone Etruscan Tomb, which features hypogeum tombs from the 3rd-1st century BC, offering a direct connection to Etruscan civilization. Additionally, the area has an "underground kingdom" of tunnels and caves beneath the city, with some historical examples visible at Hotel L'Antico Pozzo.

Are there any natural caves or formations to visit around San Gimignano?

Yes, you can explore Maurizio's Caves in Gambassi Terme, where a hermit once lived and chiseled figures into the stone. Another natural formation is Bear's Cave, a natural monument with a local legend about a bear inhabiting it.

Can I visit wine cellars or underground wineries in San Gimignano?

Yes, many wineries in and around San Gimignano offer tours and tastings in their cellars. These traditional, often underground, spaces are used for wine production and aging. Notable examples include Lunaria Tuscany, Fattoria Il Piano, Cappella Sant'Andrea, Tenuta Guardastelle, and Podere La Marronaia, where you can learn about the region's winemaking heritage, particularly Vernaccia di San Gimignano.

Are there family-friendly "caves" or underground experiences suitable for children?

Yes, Maurizio's Caves in Gambassi Terme are considered family-friendly. The excursion combines natural phenomena with the beauty of the Tuscan landscape and the unique story of the hermit who lived there, making it an interesting and feasible outing for everyone.

What outdoor activities can I combine with visiting caves near San Gimignano?

The region around San Gimignano offers various outdoor activities. You can find numerous road cycling routes, such as the Francigena Cycle Route: San Gimignano Loop, or running trails like the View of San Gimignano loop. For more options, explore the Road Cycling Routes around San Gimignano, Running Trails around San Gimignano, or Cycling around San Gimignano guides.

Are there hiking trails that lead to or pass by these underground sites?

Yes, for example, the Hidden River Trail and Sulphur Geyser leads to a cave with a waterfall, offering a beautiful hidden valley experience. The area around Castelvecchio Farmhouse and Cave is also set in a dense forest with paths through a nature reserve.

What is the best time of year to visit the caves and underground sites?

Many of the underground sites, especially wine cellars, are accessible year-round. For natural caves and trails like the Hidden River Trail, visiting during spring or autumn can be ideal for comfortable temperatures. Summer offers shade in places like the Hidden River Trail, but some natural features, like waterfalls, are dependent on water levels.

What should I wear when exploring caves or underground sites in the region?

For historical sites like the Etruscan Tomb, comfortable walking shoes are sufficient. For natural caves or trails, especially those that might be wet or uneven, sturdy footwear with good grip is recommended. Layers of clothing can be useful as temperatures underground can be cooler than above ground.

Are there any unique or unusual "caves" with interesting stories?

Yes, Maurizio's Caves in Gambassi Terme are unique as they were once home to a hermit named Maurizio, who chiseled figures into the stone. The Bear's Cave also has a local legend stating that a bear once inhabited it, adding a unique historical element to its natural formation.

Can I find ancient Roman archaeological sites related to underground structures?

Yes, in the San Gimignano area, an 1,800-year-old wine cellar was discovered at the Roman villa of Aiano. This archaeological site features a large hall with "dolia defossa" (large buried jars for wine storage) and tanks used for fermenting grape must, showcasing ancient Roman winemaking practices.

Are there any easy-to-access "caves" for beginners or those with limited mobility?

While many sites involve some walking or stairs, the historical underground examples at Hotel L'Antico Pozzo offer a glimpse into San Gimignano's hidden past with potentially easier access. Winery cellars also typically provide a comfortable and accessible experience for wine tasting and learning about production.

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