Name: 2026 Tuscany 4-to-7 day "Chianti" Ride Vacation
Location: Tuscany

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Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy &amp; Europe. Secure your spot now and get ready for the ride of a lifetime.The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

Tuscany

2026 Tuscany 4-to-7 day  "Chianti" Ride Vacation

VespingAround

This will be most likely Mauro the founder of Vesping Around or one of his closest associates

24/7 Tour Leader

Accomodation

Specified Meals

Vespa

Required to ride in Italy.   We are happy to handle the administrative tasks required to obtain your International License Permit for you. 

International License

Museum entrance, half day cooking lesson, access to 100km parade

All Planned Activities

Backpack, water canteen, rain jacket and pants, commemorative merch

Travel Kit

Exclusive Services

A Lifetime experience!

Airfare

This is required for every traveler in order to keep your booking confirmed.

Travel Insurance

Required to enter EU Countries starting mid-2025

ETIAS Visa

Transportation service from/to accommodation.  If you wish to have this prearranged, please select this option as an add-on during check out.

Shuttle Service

Train service from/to accommodation.  You will want to arrive at the Poggibonsi (Siena) station.

Train

Please add per person.  If traveling as a couple, select 2 . Ease your mind and make the experience even more enjoyable. Let us book a private driver that will pick you up/drop you off the closest train station or airport.

Shuttle to/from train station/airport 

This is based on classic room. All upgraded room will require additional fee to be billed separately.

Additional Hotel Stay day

All Vespa are 125cc automatic gear.  Most people enjoy riding together - the passenger busy capturing photos and video moments).  However, riding solo is also a vibe!

Additional Vespa

This option includes an extra day with your Vespa &amp;  will include an extra night at the same location, all activities, and meals. If you selected both Options (5a &amp; 5b), this trip will be in all effects a 6-day trip. Breakfast Ride &amp; Visit to PienzaNestled in the heart of Tuscany, Pienza is a picturesque gem waiting to enchant you. Known as the "Ideal City of the Renaissance," this charming town offers a perfect blend of history, culture, and stunning landscapes. Stroll through its narrow, cobbled streets and admire the harmonious architecture, epitomized by the exquisite Palazzo Piccolomini and the breathtaking Pienza Cathedral. Don't miss the panoramic views of the Val d'Orcia, a UNESCO World Heritage site, that stretch out before you. Indulge in local delicacies like Pecorino cheese, and immerse yourself in the serene beauty and timeless allure of this Tuscan treasure. Lunch at organic farm Overlooking Val D'orcia Valley Aperitivo inside Vineyard on the way back, Including a glass of wine and a mix board. You can order a la carte for more food or drinks.

Day 5a - Exploring Val D'Orcia (VESPA)

This option includes an extra day with your Vespa &amp;  will include an extra night at the same location, all activities, and meals. If you selected both Options (5a &amp; 5b), this trip will be in all effects a 6-day trip. BreakfastRide &amp; Visit to PienzaNestled in the heart of Tuscany, Pienza is a picturesque gem waiting to enchant you. Known as the "Ideal City of the Renaissance," this charming town offers a perfect blend of history, culture, and stunning landscapes. Stroll through its narrow, cobbled streets and admire the harmonious architecture, epitomized by the exquisite Palazzo Piccolomini and the breathtaking Pienza Cathedral. Don't miss the panoramic views of the Val d'Orcia, a UNESCO World Heritage site, that stretch out before you. Indulge in local delicacies like Pecorino cheese, and immerse yourself in the serene beauty and timeless allure of this Tuscan treasure.Lunch at organic farm Overlooking Val D'orcia ValleyAperitivo inside Vineyard on the way back, Including a glass of wine and a mix board. You can order a la carte for more food or drinks.

Day 5a - Exploring Val D'Orcia (SHUTTLE)

This option includes an extra day with your Vespa &amp;  will include an extra night at the same location, all activities, and meals. If you selected both Options (5a &amp; 5b), this trip will be in all effects a 6-day trip. Breakfast Ride to Piaggio Museum &amp; Visit of Peccioli TownPeccioli, a town in Tuscany, Italy, is known for its interesting mix of contemporary art and ancient architecture. The town has hosted internationally renowned artists since the 1990s, who have created works of art and architecture specifically for Peccioli. These contemporary pieces contrast with the town's ancient brick structures, old doors, and flowerpot-adorned houses. For example, the installation Squardo di Peccioli features hundreds of photos of eyes along an old brick wall.Lunch at local Gastro DeliPrivate Tour of Piaggio Museum &amp; Piaggio Shop with special discount.

Day 5b - Ride to Peccioli &  Piaggio

Are you feeling unsure or less than 100% confident about your riding skills?  It might be worth spending some time getting familiar with the vehicle assigned to you since the day before the tour starts. Includes:- 1 early extra night accommodation at local hotel + breakfast- 1 extra day vespa rental-1  2 hr to 3 hr safety ride course with local instructor

Learn to Vesping Ride Course:  1 driver

Are you feeling unsure or less than 100% confident about your riding skills?  It might be worth spending some time getting familiar with the vehicle assigned to you since the day before the tour starts.  Includes:- 1 early extra night accommodation at local hotel + breakfast- 1 extra day vespa rental-1  2 hr to 3 hr safety ride course with local instructor

Learn to Vesping Ride Course:  2 drivers

Are you feeling unsure or less than 100% confident about your riding skills?  It might be worth spending some time getting familiar with the vehicle assigned to you since the day before the tour starts.   Includes:- 1 early extra night accommodation at local hotel + breakfast- 1 extra day vespa rental-1  2 hr to 3 hr safety ride course with local instructor

Learn to Vesping Ride Course:  3 drivers

We at Vesping Around require the purchase travel insurance to ensure peace of mind and financial protection. Travel insurance covers unexpected events such as medical emergencies, trip cancellations, lost luggage, and delays.  It provides support and assistance during unforeseen situations, allowing travelers to fully enjoy their adventure without worrying about potential setbacks. Investing in travel insurance is a smart decision for a safe and stress-free Vespa journey.  With partnered up with Faye because of their high rated customer assistance, instant funding in case of emergency, and ease-of-use app.  You can access a link to Faye within your client portal after check out.   When you select this option, I will see you information regarding Faye and next steps.

Travel Insurance Quote 

If you indicate interest in this option, we will connect you with our travel concierge partner that will offer you personalized global travel options for your pre and post Vespa trip experience.

Travel Concierge

Commemorative Vesping Around Hat

At Vesping Around, we craft intimate riding experiences that immerse travelers in the authentic beauty of Italy. Each journey is meticulously designed to highlight hidden gems, from charming small villages to scenic countryside routes. You'll savor local cuisine, meet local inhabitants, and explore historical landmarks, all while enjoying the thrill of riding a classic italian scooter. These personalized tours promise not just a trip, but a memorable adventure that captures the essence of Italian culture and lifestyle.

Room with a Queen bed, bathroom with shower for 1 adult. Hydro shower with jets Review accommodations <a target="_blank" href="https://villasanlucchese.com/en/rooms-suites/">website</a> as a reference.

Classico - Single Occupancy

This room has a queen bed, en-suite bathroom, standing shower. Twins beds can be arranged.  Please be sure to send me a message if you would like twin beds. Review accommodations <a target="_blank" href="https://villasanlucchese.com/en/rooms-suites/">website</a> as a reference.

Classico - Double Occupancy 

Join us and ride the Tuscany hills to create an unforgettable memory. Stay at a high-end 4-star Villa on a scenic hill, explore local activities, meet the locals, and conquer a thrilling 100-kilometer ride through the Chianti Valley along with hundreds of other Vespas coming from all over Italy &amp; Europe. Secure your spot now and get ready for the ride of a lifetime. The only requirements?  Prior experience riding on a two-wheel vehicle, motorcycle, or scooter, and the desire to have a lot of fun!

About this trip

An authentic immersive e oerience in the history, topography, food and culture of Puglia! First class accommodation!

2025 Sept 6-13, Puglia "Valle D'Itria" Ride Vacation

We had a great time!  Creativity provided an interesting itinerary!  Vespas were in great condition and fast.  This was our second trip with Mauro and it won’t be our last.  Ps, did I mention lots of great food ❤️

2026 Tuscany 4-to-7 day  "Chianti" Ride Vacation in Tuscany

2026 Tuscany 4-to-7 day "Chianti" Ride Vacation

2026 Tuscany 4-to-7 day "Chianti" Ride Vacation

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