Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Bike touring routes & trails
Italy
Tuscany
Florence
Castelfiorentino

View of San Gimignano – San Gimignano Panoramic Trail loop from Castelfiorentino

Routes
Bike touring routes & trails
Italy
Tuscany
Florence
Castelfiorentino

View of San Gimignano – San Gimignano Panoramic Trail loop from Castelfiorentino

Expert

4.6

(60)

306

riders

View of San Gimignano – San Gimignano Panoramic Trail loop from Castelfiorentino

05:15

74.6km

1,210m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: September 16, 2025

Download GPX

Save

Move start point

Edit route

Navigate

Send to Phone

Tips

Includes a segment that goes up or down a series of steps

You may need to carry your bike.

29 m in total

Waypoints

A

Start point

Train Station

Get Directions

1

14.5 km

View of San Miniato

Highlight • Viewpoint

Panorama of San Miniato with the Prato della Rocca - the brick keep on the flattened hilltop - and the bell tower of the Prato del Duomo.

Translated by Google •

Tip by

2

16.1 km

San Miniato Cathedral and Clock Tower

Highlight • Religious Site

San Miniato, city of good cuisine and white truffles, looks from a hill over the plain through which the Arno flows. The monumental palaces prove its grandeur, but all its …

Translated by Google •

Tip by

3

16.2 km

Piazza della Repubblica and Bishop’s Palace

Highlight • Historical Site

Along the Via Francigena, Piazza della Repubblica is surrounded by the facade of the Bishop's Seminary dating back to the 16th century.

Translated by Google •

Tip by

4

21.1 km

View of the hills along Via Castel Fiorentino

Highlight • Viewpoint

This stretch of Via Francigena that goes from San Miniato to Gambassi offers breathtaking views of the surrounding hills.

Translated by Google •

Tip by

5

24.9 km

Cypress Avenue

Highlight • Natural

beautiful avenue with cypresses up on an unpaved surface. It is the classic Tuscan avenue, full of beauty, especially at dusk

Translated by Google •

Tip by

6

55.1 km

View of San Gimignano

Highlight • Viewpoint

Great view of San Gimignano.

Translated by Google •

Tip by

7

57.6 km

San Gimignano Panoramic Trail

Highlight • Trail

San Gimignano with its towers stands out over the surrounding countryside.

Translated by Google •

Tip by

8

60.0 km

Castello di Uzzano

Highlight • Castle

B

74.6 km

End point

Train Station

Way Types & Surfaces

Way Types

65.7 km

5.44 km

3.27 km

153 m

< 100 m

< 100 m

Surfaces

61.0 km

8.11 km

5.39 km

138 m

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

Highest point (520 m)

Lowest point (40 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by AerisWeather

Today

Sunday 2 November

20°C

13°C

0 %

If you start your activity now...

Max wind speed: 7.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Loading

Nearby routes

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.3

130

From Colle Val d’Elsa to San Gimignano

02:48h

37.5km

730m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.3

50

Panoramas around Greve in Chianti — Loop tour

02:09h

30.1km

600m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.2

52

San Gimignano — Ring tour

02:24h

29.3km

570m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

3.8

18

The art city of Firenze — Ring tour

01:54h

28.3km

360m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.9

2,959

Radda in Chianti – San Donato in Poggio loop from Panzano in Chianti

03:18h

46.7km

830m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

4.7

17

Chianti and its olive trees — Ring tour

01:25h

19.2km

400m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.7

21

The villages of Montefoscoli, Palaia and Toiano — Ring tour

02:07h

28.2km

510m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

1.0

5

Colle di Val d'Elsa e Poggibonsi — Ring Tour

01:44h

22.9km

300m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

3.3

8

Volterra and its landscapes - Ring tour

00:54h

11.0km

330m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.9

391

View of San Gimignano – View of Monteriggioni Castle loop from Castellina in Chianti-Monteriggioni

05:13h

71.1km

1,020m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.6

306

View of San Gimignano – San Gimignano Panoramic Trail loop from Castelfiorentino

05:15h

74.6km

1,210m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.0

235

View of Monteriggioni Fortress – View of Monteriggioni Castle loop from Castellina in Chianti-Monteriggioni

04:21h

64.4km

750m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepacking
B2B
PartnersConnectEmbed routes
Company
PressWhat's NewPioneersProduct UpdatesAmbassadorsAdventure Hub
Community
Help GuidesSupportKomoot Treasure Hunt
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy
Terms of Service
Community guidelines
Vulnerability disclosure program
Imprint
Information for law enforcement