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Chianti Classico Self-Guided Tour

This 3-day, 2-night getaway starts in Firenze (aka - Florence) where you will be given your scooter(s). Then you are on your way! Soon you will be seeing the wonderful views over the heart of Chianti, taking in a string of medieval castles which were the front line in the battles between Florence and Siena.

This is a self-guided tour -- meaning, you are in control. While we at LSVT will make suggestions, you get to pick and choose what to do as you desire. Do you want to be an early bird, have that first of the morning cappuccino and get on the road? Maybe you feel like sleeping in and having a leisurely scoot to lunch? This self-guided tour allows you to choose the adventure. Do you visit historical towns? Cruise past olive groves on quiet Chianti roads? Find yourself in a small hamlet on the top of a hill admiring the countryside? Maybe all of the above? 

Day 1: Start your day by picking up the scooter(s) in Firenze/Florence 
Ride Suggestion: GreveRaddaBrolio Castle
Start your day in: Florence          End your day in: Radda in Chianti 

Day 2: Ride Suggestions: Siena, and/or perhaps Monteriggioni and Castellina; maybe enjoy riding around Chianti and stopping in smaller villages (Volpaia, Gaiole, Vertine) as you desire
Start your day in: Radda in Chianti          End your day in: Radda in Chianti

Day 3: Ride Suggestion: Monteriggioni and Castellina or cruise through Lecchi for a last cappuccino or gelato → return scooter(s) in Firenze/Florence
Start your day in: Radda in Chianti          End your day and tour in: Fabulous Florence 
Nightly Lodging for your 2 nights will be in Radda in Chianti.

Tour Details:
   Dates: private departures from March to October
   Starting/Ending Location: Firenze/Florence
      For an additional charge, scooter(s) can be picked up, dropped off, or both in Radda in Chianti.
   Price: US$350* per person based on double occupancy for 2 nights. 
      Note: Couples can share a scooter and save $60 for one person. 

* - This prices covers 2-nights lodging and 3-days of scooter rental. It does NOT cover fuel for the scooter or for you (i.e. meals, snacks, coffee, gelato, pizza). The Vespa/scooter will be given to you full, plan to return it full. As to how hungry/full you are -- that's up to you.  


Radda has been inhabited since the 9th century, and was officially mentioned in a document from 1002. Its stone facades add to the medieval look characterized by narrow streets and tower buildings. It is not a big place; so wander, you won’t get lost.


This small borgo, or hamlet, has been completely restored and truly speaks of its origins and importance in the area. It was one of the main defending structures in Chianti, and boasts defending walls, medieval towers and castle, and dominant panoramic positions.

Volpaia is one of many small villages you can discover and explore while riding in Chianti. 


The city's origins go back to Etruscan times of which there are many visible remains to explore both in the excavations at the well marked archeological sites and in the Archeological museum in the city center. The Florentines turned Castellina into an important stronghold due to its strategic position between Florence and Siena. The town was destroyed and rebuilt many times during the battles between the two cities and every time the town was reconstructed, they made bigger defensive walls. Legend has it that even Brunelleschi (he of the famous Firenze dome) was asked to work on the project of new walls for the town. Today, you can enjoy a pedestrian-only zone filled with local shops and restaurants in the historical center.


Its strategic position at the crossroads of three important pilgrimage roads; the Chiantigiana road, the road to Valdarno, and the road to Val di Pesa, favored its economic growth. Piazza Matteotti, while not a “square” square, is the focal point of the town. The piazza has a portico on three sides serving as the frame for shops, artisans’ workshops and restaurants, including the Antica Macelleria Falorni, a Tuscan butcher shop that has been in the same spot since 1729. More shops and enticing restaurants are also located down via Roma and via Garibaldi, at the top and bottom of the square. The beauty of Greve is that it is compact and you can easily visit everywhere by foot.

Nearby, perched on a hill above Greve, is a small fortified village from the early 900’s, Montefioralle. The explorer Amerigo Vespucci was born here; his ancestral home is located along the main street. The family's coat of arms with a wasp above its doorway distinguishes the home. You can ride up to the little town, following a steep road with many tight curves and panoramic views.


The castello (castle) was built sometime in the middle ages. The Ricasoli family acquired it in 1141, and still maintains ownership. Certain parts of the castle cannot be toured as the family still uses them privately. Through the centuries the castle has suffered attack and destruction in numerous historical battles, from Aragonese and Spanish attacks during the fifteenth century, to disputes in the seventeenth century right through to bombings and artillery attacks during the Second World War.

The Barone Ricasoli is the fourth longest-lived company in the world in the same place and the second in the wine sector. Barone Ricasoli is the oldest winery in Italy. These are some wonderful wines. We recommend touring the castello. Your entrance fee allows you a sample in the tasting room (below the castle); you can purchase additional tastings. You can visit the tasting room separate from the castello. The “Osteria del Castello” offers very good food.


Medieval Florence’s rival; Siena was a major trader with all of Europe. Then in 1348, the bubonic plague cut Siena’s population by more than a third and it never really recovered. In the 1550s Siena lost its autonomy to Florence, which punished Sienna by keeping it a backwater village with little growth.

Siena was the first European city to ban auto traffic in its main square, Il Campo. The square is more an amphitheater, surrounded by eateries (with some would say, jaded staff), the location of the Il Palio horserace, and is the heart of Siena. Siena’s duomo has one of Europe’s most extravagant facades, inlaid-marble floors, and sculptures by Bernini and Michelangelo.


Siena built the village’s fortifications around 1213 to protect it from its rival Florence, but was surrendered to the Medici in 1554. Luckily, the walls still stand.

Monteriggioni is not big. Depending on your interests, a visit of 30-minutes to 2-hours is probably sufficient. Besides being a stop for pilgrims on the Via Francigena, Monteriggioni is on the tourist path so it offers visitors several eateries.

The Tuscan poet Dante Alighieri used Monteriggioni’s 14 towers to evoke the sight of the ring of giants encircling the Infernal abyss in his Divine Comedy. At some point, all of the towers have been lowered. In 1921, three were lowered to the height of the wall. Why? No one now knows.