2 Day itinerary in Italy, Europe
If you want to connect with Tuscany’s nature and local life, allow yourself the extra time to travel off the beaten path and let us take you to meet and discover the Chianti Classico wine region. We will cross it on a bike all the way from the northside (San Casciano) to the Southside (Gaiole in Ch... Read More
By Andrea
Physical Difficulty
Recommended Age
Operated in
GUIDANCE
starting point
trip type
trip attributes
Rural home stays
Indigenous culture
Visit markets
Meet local people
Outdoors & Nature
Culture & Arts
Food & Drink
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Night
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Discover the Chianti Classico wine region
Travel through backroads and see the best medieval towns
Learn about wine and olive oil making
Eat traditional food in local trattorias and farms
Discover the Chianti Classico wine region
Travel through backroads and see the best medieval towns
Learn about wine and olive oil making
Eat traditional food in local trattorias and farms
Mid-Range Accommodation
Accommodation Categories
Start your first day with our famous Chianti Classico Bike Tour and then keep riding!
Morning bike ride – start with our Chianti Classico bike ride! The first part of the bike ride lasts about 1.5 hours, and you will see typical Tuscany villages and Chianti wine fields while enjoying panoramic stops to take some photos and learn about local life and nature from our knowledgeable guide. We will then have a stop also in San Casciano, one of the main villages of the Chianti region, and see the ancient city walls. After another bit of biking, we will reach the wine estate for a tour of the property and a full Tuscan lunch! Lunch and tasting – visit an exclusive Chianti Classico Villa and winery with an underground cellar The ancient cellars are below the beautiful Villa and the Italian-style gardens that we will visit. We will also have a peek at the “Orciaia“, a room filled with giant terracotta pots where wine and oil used to be stored since Roman times, and the “Frantoio“, the facility where the olives are pressed to produce the world-renowned Tuscan Extra Virgin Olive Oil. We are then ready for a full Tuscan lunch and tastings at the Osteria of the Villa. Lunch includes an appetizer, first course, dessert and coffee! We will also taste 3 different wines and 2 types of olive oil, all produced on the premises. Afternoon Bike Ride – on the way to Panzano in Chianti After lunch, we will start biking again towards the medieval town of Mercatale and Greve, with a little stop for another coffee in the beautiful piazza. The last biking section will be the most challenging, as we will ride up toward the hilltop town of Panzano in Chianti, to visit our friend and world-renowned butcher, Dario Cecchini. Around 4.30pm we will reach the beautiful Villa where you will finally relax in your private room and have access to the pool if the weather allows. A full Tuscan dinner is included as well!
Guide: Included for the day
Meals: Lunch
Accommodation:
Discover Radda in Chianti, Gaiole, Pianella and Siena
After breakfast at the hotel, we start out descending downhill for several kilometers, leading us to the town of Radda in Chianti for our first climb. After a stroll through the famous town, another downhill takes us to lunch in the town of Gaiole, home of the world-famous vintage bike race called L’Eroica. While sitting in the main square of Gaiole, we introduce you to our longtime friend and local restaurant owner, Fernanda, who will serve us a delicious Tuscan lunch. After coffee, we ride back on the bikes for a nice long meandering, semi-downhill, flat stretch of road before we come to the town of Pianella. After Pianella, we can stop here or proceed uphill to Siena (in our van or still pedaling), where we will say goodbye and our amazing experience together will officially end.
Guide: Included for the day
Meals: Breakfast, Lunch
Accommodation
Meals
Transport
Activities
Extras
Not Included
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$642.00 USD