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Hills & Valley Self-Guided Tour

This 5-day, 4-night getaway starts in Firenze (aka - Florence) where you will be given your scooter(s) and a brief orientation talk. Then you are on your way into the heart of the Chianti region, one of the most picturesque areas of Tuscany. While Cosimo III de' Medici, Grand Duke of Tuscany, issued an edict in 1716 officially recognizing the boundaries of the Chianti district, which was the first legal document in the world to define a wine production area; now there is so much more to Chianti.

To the West of Chianti lies the Elsa River Valley, or Valdelsa. This was the center of Etruscan civilization. Under the Medici family the area became more agricultural. Here you can ride on long sweeping roads overlooking vineyards and saffron fields; discover your favorite gelato shoppe; and explore medieval towns to your heart's content.   

This is a self-guided tour -- meaning, you are in control. We are here to lend our knowledge so you get the trip filled with what you want to do and see.

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: Ride to Siena and perhaps Monteriggioni; visit Badia a Coltibuono for a cooking class, a walk in the garden, or wine/olive oil tasting; 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: Ride to Panzano CastellinaColle Val d’Elsa for the night
Start your day in: Radda in Chianti          End your day in: Colle Val d'Elsa

Day 4: Ride Suggestion: Ride to Volterra or San Gimignano 
Start your day in: Colle Val d'Elsa          End your day in: Colle Val d'Elsa

Day 5: Ride to San Gimignano → return scooter(s) in Firenze/Florence  
Start your day in: Colle Val d'Elsa          End your day and tour in: Fabulous Florence 

Lodging for 2 nights in Radda in Chianti, followed by 2 nights in Colle di Val d’Elsa.

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$900* per person based on double occupancy for 4 nights. 
      Note: Couples can share a scooter and save $100 for one person. 

* - This prices covers 4-nights lodging and 5-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.  

See this page for fun facts on towns in Chianti, Sienna, and Monteriggioni. 


Panzano, located almost directly in the middle of the constantly feuding powers of Siena and Florence, was destroyed in 1260, again in 1397, and then again in the 1400’s and 1500’s when it changed hands back and forth between Florence and Siena.

The main square is home to several outdoor restaurants and cafes, where you can enjoy the small town atmosphere with a tasty little treat. If you are looking for something a bit more “substantial,” then head towards Macelleria Cecchini, where 8 generations of butchers have dazzled the locals and tourists alike with a bit of fanfare and delicious meats.


A walled ancient town. Colle is divided into Colle Alta (built on a hilltop) and Colle Bassa (the lower part). Colle was historically controlled by either Florence or Siena. Many Etruscan and Roman remains have been found in Colle and its surroundings. The famous Via Francigena did (some routes still do) pass through the upper part of the Val d'Elsa (or Elsa Valley), ensuring all the area wealthy conditions and economical benefits.

Today Colle Val d'Elsa is famous for the production of crystal items. Not far from the main town is Le Caldane, natural hot thermal springs whose waters are renowned since ancient times for their curative properties. There are several pools, all dating back to the XIIIth century, destroyed and then partially restored during the XVth and XIXth centuries.


The Etruscans of Italy, from around 700 B.C. predated the Greeks and Romans; and were the foundation of the later Roman Empire. Volterra was one of their most important Etruscan cities in its day. The cliffs here inspired Dante’s “cliffs of hell”. In winter, clouds come from below the cliffs, so Volterra is seen as floating.

While a hill town, Volterra feels bigger than other hill towns and not so dependent on the tourist dollar. Besides its duomo and main square, you can visit an excavated roman theatre from 1 B.C., a park formed where the town acropolis was, churches, museums, and alabaster artists at work.


Imagine this hill town with its original 72 towers, not just the remaining 14. Before the towers became monuments to noble familys’ wealth, they offered protection from invaders. Ladders connecting each level would be pulled up and the external wooden staircase to the entrance burned. Today, San Gimignano is known for producing some of the best saffron in Italy and the white wine, Vernaccia di San Gimignano. It also offers visitors a duomo, several piazzas, shopping, eateries, and a handful of museums.