Tour Description

Welcome to the most iconic way to experience our homeland. I invite you to feel the true freedom of Tuscany through an exclusive, deeply personal journey meticulously organized down to the smallest detail by me, Niccolò. Thanks to a special partnership with an exclusive local rental provider, we have crafted a seamless, premium adventure that takes you off the beaten path and into the postcard-perfect landscapes of the Chianti Classico region. From start to finish, you will have my continuous, dedicated assistance for a flawless, stress-free day.

Door-to-Door Premium Comfort: Your day begins effortlessly. We will personally pick you up from any location or accommodation of your choice in our premium, comfortable vehicle to bring you to our starting base, and we will drive you safely back at the end of the day.

1. The Ride: Cruising the Iconic Chiantigiana Road

After a full safety briefing, you will hop onto your own original Piaggio Vespa 125cc to begin a spectacular ride. We will cruise along the world-famous Chiantigiana road, legendary for its winding curves, cypress-lined avenues, and breathtaking, sweeping views over endless vineyards and olive groves. Feel the Tuscan breeze as you explore the rolling hills exactly like a local. (Please note: Each participant will ride their own individual Vespa for an independent, thrilling experience).

 2. The Route: Two Historic Medieval Borghi between Florence & Siena

Led by our expert private guide, we will journey through the heart of the territory, exploring the historic borderlands stretching beautifully between Florence and Siena. We will stop to visit two of the finest, most spectacular medieval villages (borghi) in the entire region. You will have time to walk their ancient stone streets, soak in the timeless atmosphere, and capture stunning photos of these hidden historical gems.

 3. The Reward: Intimate Family Cellar Visit, Wine Tasting & Lunch

After an incredible ride, it is time to park the Vespas and reward our senses. We will head to a hand-selected, intimate family-run cellar boasting an absolutely magnificent, panoramic view over the valleys. Together with the local wine producers, you will enjoy a private tour of the estate, followed by a premium wine tasting paired with a complete, traditional Tuscan lunch.

A Relaxing Return: Once the tour and lunch are complete, you can fully indulge in the local wines without a single worry. Our professional support Jeep will handle the return transfer, allowing you to completely relax, unwind, and enjoy a peaceful ride back to your villa or hotel.

What’s Included 

• Personal Planning & Continuous Assistance by Niccolò: Complete itinerary management and dedicated support by Niccolò.

• Any-Location Private Pick-up & Drop-off: Professional door-to-door transfers in our comfortable vehicle.

• Original Piaggio Vespa 125cc or vintage 500 fiat : A beautifully maintained, authentic Italian Vespa for each individual rider or vintage fiat 500 .

• Professional Private Guide: Continuous leadership and assistance from our expert local guide throughout the entire riding route.

• Safety Equipment & Insurance: Professional helmet and civil liability insurance (RC insurance) included for peace of mind.

• Two Historic Borghi Visits: Guided stops and exploration of two legendary medieval villages located between Florence and Siena.

• Support Vehicle Assistance: A dedicated support Jeep following the tour for maximum safety and to provide a completely relaxed, stress-free return after lunch.

• Exclusive Cellar Visit & Wine Tasting: Private estate tour and a premium guided tasting of elite regional wines.

• Full Traditional Countryside Lunch: A complete, authentic meal served at the panoramic winery following the ride.

Important Experience Details & Safety Policies

• Duration: Approximately 5 hours total ( Riad time, village exploration, and a relaxed wine-pairing lunch).

• Languages: The tour is conducted in English (and available in Spanish upon request).

• Rider Requirements: Drivers must be at least 18 years old and possess a physical, valid driver’s license (digital copies or photos are not accepted).

• Riding Flexibility & Alternatives (Le Nostre Alternative): Your safety and comfort are our absolute priorities. If any guest does not feel 100% confident or capable of driving a Vespa, we offer excellent alternative options so no one misses out on the fun:

  • You can comfortably enjoy the exact same tour riding as a passenger seated behind one of our professional expert guides.

  • You can switch to driving or riding in one of our vintage Fiat 500 iconic classic cars.

• Inclement Weather Policy (In Caso di Pioggia): Rain will not ruin your Tuscan dream! In the event of bad weather or rain, the tour will seamlessly transition into a spectacular Vintage Fiat 500 Classic Car Tour, allowing you to explore the villages and reach the family cellar in perfect comfort, style, and safety.

• The Custom Touch: This itinerary is fully customizable. Contact me directly to adjust the details, mix experiences, or perfectly design your custom days in Tuscany!