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 & 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!
24/7 Tour Leader: This will be most likely Mauro the founder of Vesping Around or one of his closest associates
Accommodation: 8 night at a High End Boutique Hotel
Specified Meals: 8 breakfasts, most lunches & dinners
Vespa: Rental, helmet, top case, insurance
International License: Required to ride in Italy. We are happy to handle the administrative tasks required to obtain your International License Permit for you.
All Planned Activities: Museum entrance, half day cooking lesson, access to 100km parade
Travel Kit: Backpack, water canteen, rain jacket and pants, commemorative merch
Exclusive Services: Travel Insurance, Travel Concierge
A Lifetime Experience!
Airfare: Recommended FLR or SAY
Travel Insurance: This is required for every traveler in order to keep your booking confirmed. Vesping Around recommends Faye.
ETIAS VISA: Required to enter EU Countries starting 2026
Shuttle Service: Transportation service from/to accommodation. If you wish to have this prearranged, please select this option as an add-on during check out.
Train: Train service from/to accommodation. You will want to arrive at the Poggibonsi (Siena) station.
Gas
The 4-star accommodation is going to be in the vicinity and a stone throw of all activities scheduled for the week.
Join us for a 3-course meal in what it will be our home for the next 8 days. During dinner, we will welcome our group and review what's in store over the coming week!
We'll head to meet the local Vespa Club and the other hundreds participants of the 100KM Chianti for a quick ride and an aperitivo in nearby San Gimignano, stopping in some local towns on the way there.
Dinner will be at this monastery ground and supplied by Netflix-famous Chef.
We depart early morning for a Chianti valley tour on paved roads through famous Chianti valley towns. This is going to be a lifetime experience as you ride up and down Tuscany hills like you've seen in the movies. We will make stop to charming little towns for espresso or a glass of wine, before continuing to the official wine tasting and a small sandwich at a Netflix-famous local butcher shop along the way.
Today we will enjoy a cooking class with a local native at a farm in the Chianti Hills. What might be on the menu?
fried zucchini flowers
spinach & ricotta ravioli
second course chicken cacciatore
tiramisu
Afterward, we ride to beautiful hidden gem Certaldo Alto for gelato.
Check out & Arrivederci!
Exploring Val D'Orcia
Breakfast
Ride & Visit to Pienza
Nestled 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.
Ride to Peccioli & Piaggio/Vespa Museum
Breakfast
Ride to Piaggio Museum & Visit of Peccioli Town
Peccioli, 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 Deli
Private Tour of Piaggio Museum & Piaggio Shop with special discount.
Classico - Single Occupancy
Available until April 1, 2026
Room with a Queen bed, bathroom with shower for 1 adult. Hydro shower with jets
Review accommodations website as a reference.
Pricing: $2,850
Deposit: $500
Classico - Double Occupancy
Available until April 1, 2026
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 website as a reference.
Pricing: $2,485
Deposit: $500
Available until May 19, 2026
All Vespa are 150cc automatic gear. Most people enjoy riding together - the passenger busy capturing photos and video moments). However, riding solo is also a vibe!
Pricing: $450
Deposit: $225
Available until May 19, 2026
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
Princing: $350
Deposit: $175
Available until May 19, 2026
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
Pricing: $500
Deposit: $150
Available until May 19, 2026
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
Pricing: $600
Deposit: $300
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.
Pricing: $200
Deposit: $100
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.
Pricing: $0
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.
Commemorative Vesping Around Hat: $25
Commemorative Vesping Around T-shirt: $35
If purchasing more than 1, please indicate size for each within the participant information in step 2 of the checkout process.
Available until 15 days before departure
This option includes an extra day with your Vespa & will include an extra night at the same location, all activities, and meals.
Breakfast
Ride & Visit to Pienza
Nestled 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.
Pricing: $350
Deposit: $100
Available until 15 days before departure
This option includes an extra day with a private SHUTTLE & will include an extra night at the same location, all activities, and meals.
Breakfast
Ride & Visit to Pienza
Nestled 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.
Pricing: $350
Deposit: $100
This option includes an extra day with your Vespa & will include an extra night at the same location, all activities, and meals.
Breakfast
Ride to Piaggio Museum & Visit of Peccioli Town.
Peccioli, 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 Deli
Private Tour of Piaggio Museum & Piaggio Shop with special discount.
Pricing: $220
Deposit: $100
At Vesping Around, we craft intimate Vespa 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 passionate Vespisti from local clubs, and explore historical landmarks, all while enjoying the thrill of riding a classic Vespa. These personalized tours promise not just a trip, but a memorable adventure that captures the essence of Italian culture and lifestyle.
Call or Text: 888 773 2910