Skip to main content
Great cycling rides logo Trek Travel

Gaiole in Chianti to Villa a Sesta Loop

Gaiole in Chianti to Villa a Sesta Loop

#6 on our Great Rides list


Tuscany is one of the places to cycle that people dream of. Ribbons of road carving through the mountains and hillsides, mountain tops dotted with quaint villages, world-renowned food, amazing wine, and Italian hospitality.


Gaiole in Chianti, Tuscany, Italy

light blue icon link


35 miles / 56.5km

light blue two peak mountain icon

Elevation Gain

3,819ft / 1,164m

light blue cloud and sun icon

Best Time to Visit

Spring or Fall

light blue road icon


Paved Road

light blue icon that depicts that something is loading.


Level 3

light blue stoplight icon with boarder


Level 1

Discover this ride on our Tuscany bike tour

Quintessential Luxury of Chianti’s Famous Castles and Wines

Truly, what more could one want and desire.

Today’s ride is a stunning loop from the village of Gaiole in Chianti heading out of the mountains and winding through the vineyards. Around 10km, the famed Castello di Brolio is just off our path. After passing the castle, the mountainous landscapes of Chianti give way to olive groves, vineyards, and gentle rolling roads snaking through the countryside. Around 30km into the ride, you will pass through Castelnuovo Berardenga, this is a great spot to refuel as you begin your ascent up Monteluco. The next 14.5km will take you to the top of today’s climb, which will average just over 3%. After ascending to the top, there is a little store to top up on water, and then you can enjoy the descent which will take you almost all the way back to our hotel.

What you need to know

The first 25km of today’s ride is mostly downhill, averaging -0.1%. And different points of the ride, on a clear day, Sienna is off in the distance less then 20km away.

Cycling in Chianti, the temperatures can be relatively cooler throughout the year, relative to those in Sienna. It is always wise to take layers with you, and prepare for the unexpected. Chianti seems to receive slightly more rain then some of the surrounding areas.

Great locations to refuel on the ride, 10.2km there is a cafe and the Enoteca of The Castello di Brolio. The next recommended stop for food and water is just before the 30km mark in Castelnuovo Berardenga. The final spot is on top of Monteluco at 44.2km.

While you’re in town

The village of Radda in Chainti is just 11km away. For those looking to explore another quaint village with fantastic wines and restaurants, it is worth a stop. Bar Dante is a great place to sit and sip a drink, while meandering through the village you will find great cycling shops, and Enoteca’s.

If you have a desire to cycle the White Roads on a vintage bike, simply stop in to La Bottegga and talk to Emanuele Nepi (he is one of the owners). He will be able to help you find a vintage bike to rent, along with getting you in the vintage gear.

Siena is only 25km away, and it is well worth the trip. From exploring the Duomo di Siena, Tower of Mangia, and the Piazza del Campo are highly recommended. The La Bottega dei Sapori Antichi is a great spot to grab a sandwhich to go, while GROM – Il Gelato come una volta & Gelateria Kopakabana are our favorite spots for Gelato.

Ready for this ride?

Book early and save. We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.


If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date?
Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Level 2:

Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Level 3:

Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself