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    Gaiole Loop

    Difficulty
    This reflects the 10Adventures difficulty rating for each route. We aim to keep ratings consistent across regions.
    Moderate
    Duration
    This reflects the estimated time the majority of users will take on this trail. If you are slower, add time to the top-end figure. If you are fast, then you may complete this route faster than this time range.
    3.5-5h
    Distance
    This reflects the return distance of this route as measured by the GPS file.
    15.0 km
    Elevation
    This reflects the total elevation gained throughout this route as measured by the GPS file. This includes all ascents and descents, and is higher than what is quoted in most route guides, which simply measure the distance between the starting-point and high-point of the route.
    326 m
    User Ratings
    These ratings are completed by users who have completed this trail and not subject to reviews by 10Adventures.
    Overall Rating
    This is the average user-submitted overall rating on a scale of 1 to 10, with 10 being the highest.
    9.7
    Physical Difficulty
    This is the average user-submitted rating on the physical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
    Easy (Circle)
    Suitable for beginners, families, young children, and those looking for a casual adventure.
    Technical Difficulty
    This is the average user-submitted rating on the technical difficulty of this route. In general, green is beginner, blue is intermediate, black is advanced/most difficult and double-black is expert-only. It is recommended that users build up to black and double-black routes.
    Easy (Circle)
    Suitable for beginners, families, young children, and those looking for a casual adventure.
    Read Reviews
    Directions to Trailhead
    Small rocky wall along the trail of Gaiole Loop Hike in Tuscany, Italy

    The Gaiole Loop is a popular day hike in Tuscany, easily accessible from Siena. This walk starts with a steep ascent out of Gaiole in Chianti that brings you to the Badia Coltibuono Abbey and then down through the picturesque village of Montegrossi. Descend through cool forests as you make your way back to Gaiole.

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    Route Description for Gaiole Loop

    Start on the pedestrian-only Via Bettino Ricasoli in Gaiole and walk roughly north, past the Co-op. Take your first right onto Via Baccio Bandinelli. At the T-intersection, go right. Go left at the second T-intersection. It’s a steep climb and the blood will get moving and you’ll heat up quickly.

    Go up and over the first hill and down and up another. Ignore markings that may indicate taking a road on the right. Along the way you’ll pass the turn off for Riecine Winery, where you can book a tour. Riecine is a great stop for Sangiovese lovers, with a recent Chianti Classico receiving a 94 rating from James Suckling. As you climb you will pass olive groves and vineyards.

    After about 2.0 km and a lot of uphill, you will come to an old brick and stone building. Don’t be surprised if you’re pretty tired by the steep uphill.

    After a 3.3 km grind from start, you will come to a paved road. Go right and stay on this road for 140 meters then take the first left, signed to Badia Coltibuono. Immediately take a right and head down this road for 800 m. Do not take the dirt road on the right.

    Badia a Colitbuono is a stunning 1,000-year-old abbey. It has cooking classes as well as wine and olive oil tastings. Check times and book in advance if you want a tour. Go to the far end of Bada a Colitbuono to get in.

    Retrace your steps back to the main road and then immediately go across the larger road, onto a paved road heading uphill - Strada di Montigrossi.

    At 5.7 km you will pass some abandoned red brick buildings. Soon after, look up to your left for another abandoned building, Castello di Montegrossi. From here you will quickly come to the cute little town of Montegrossi. Stay on the same road, all the way through town and it will turn back to gravel. At the first junction take the left-hand path, and then the next right at the next junction, signed for Montelucci.

    At the third junction go right again. The gravel road feels tremendously remote here. Almost no sound and just peaceful tranquility.

    At 8.3 km ignore the trail going up off the right. Stay on this trail named Barbischio Ensoli. 350 m later you will come to a T-junction, go right. Where the road splits 400 m, go right again, onto Via G Marconi. Continue along this road back into Gaiole and all the way back to the pedestrianized street, now a perfect place for a coffee or a glass of Chianti Classico.

    Insider Hints for Gaiole Loop

    • Gaiole is a pretty little town, though not very touristy. It’s a fun place to be based for a night.
    • Gaiole is famous for the L’Eroica bike race, a 209.0 km bike race with almost 4,000 m of elevation gain. Most competitors usually take 15 hours to complete this challenging race.

    Getting to the Gaiole Loop Trailhead

    From Siena, you can either drive to Gaiole or take bus no. 127 going to Gaiole in Chianti.

    Route Information

    • When to do

      May - October

    • Backcountry Campsites

      No

    • Pets allowed

      Yes - On Leash

    • Family friendly

      Older Children only

    • Route Signage

      Poor

    • Crowd Levels

      Low

    • Route Type

      Loop

    Gaiole Loop Elevation Graph

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    Gaiole Loop Reviews

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