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: all nights at a High End Boutique Hotel
Specified Meals: breakfasts, most lunches & dinners
Vespa: Rental, helmet, top case, insurance
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
International License: Required to ride in Italy.
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
Experience the charm of this hand-picked Hotel & Spa, situated in the historic center of Colle di Val d'Elsa. This beautifully restored 13th-century building offers a luxurious spa and gourmet Tuscan dining. Enjoy breathtaking countryside views from the rooftop terrace while immersing yourself in rich local history.
Please note that the hotel arrangement could change and that confirmation of the stay and other details of the trips will be received not later than 30 days before arrival date.
This high-end boutique accommodation is going to be in the vicinity and a stone throw of all activities scheduled for the week.
We will take quick afternoon welcome ride to explore the immediate surrounding of the area and get confidence with our vehicles
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!
Lunch at Authentic Trattoria
Enjoy lunch at Authentic tuscan food Trattoria.
Easy day and visit to nearby medieval gem Monteriggioni.
Visit of historic San Gimignano
After heading back to our accommodations, the rest of the day is free for you to explore solo.
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.
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 an authentic wine tasting in a local wineyard.
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.
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