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

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 40 days before departure

Room with a Queen bed, bathroom with shower for 1 adult. Hydro shower with jets

Review accommodations website as a reference.

Pricing: $2,950
Deposit: $500

Classico - Double Occupancy

Available until 40 days before departure

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: $2,650
Deposit: $500

Available until 31 days before departure

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 15 days before departure

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: $150

Available until 15 days before departure

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: $300

Available until 15 days before departure

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: $400
Deposit: $100

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: $100
Deposit: $50

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.