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Tuscany 4-day 4-night Chianti & VESPA CLUB Experience

June 19 - June 23, 2026- Group size: 10 - 20
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About this trip

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!

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Inclusions

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What’s included

  • 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!

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What’s not included

  • 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

Overview

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Overview

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About this trip

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1. Tuscany

Tuscany, Italy

2. San Gimignano

53037 San Gimignano, Province of Siena, Italy

3. Tuscany Villa Chianti Hills

Via Sette Ponti Ponente, 23 B, 52024 Loro Ciuffenna AR, Italy

4. Val D'Orcia

3H75+HQ, 53027 San Quirico d'Orcia, Province of Siena, Italy

5. Pienza

53026 Pienza, Province of Siena, Italy

6. Palazzo Piccolomini, Pienza

Piazza Pio II, 2, 53026 Pienza SI, Italy

7. Pienza Cathedral

Piazza Pio II, 2, 53026 Pienza SI, Italy

8. Peccioli

56037 Peccioli, Province of Pisa, Italy

9. Piaggione

55100 Piaggione LU, Italy

10. Museo Vespa

Via Cavour, 304, 00184 Roma RM, Italy

Day 1

Friday, June 19
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Check-in at Accommodation & Welcome Dinner

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!

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Day 2

Saturday, June 20
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Meet & Aperitivo with Vespisti in San Gimignano

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Breakfast

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Meet with local Vespa Club

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.

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Dinner at outdoor location

Dinner will be at this monastery ground and supplied by Netflix-famous Chef.

Day 3

Sunday, June 21
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100 Km Chianti Valley Ride

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Breakfast

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Chianti 100Km Tour

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.

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Afterwards we will enjoy a celebratory late lunch/early dinner with 20+ Italian Vespa Clubs

Day 4

Monday, June 22
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Country Cottage Cooking Day & Gelato in Local town

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Breakfast

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.

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Day 5

Tuesday, June 23
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Ciao Ciao Belli!

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Breakfast

Check out & Arrivederci!

Day 5 (Options a & b)

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Day 5A (Option 1)

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.

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Day 5B (Option 2)

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.

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Pricing and Add-Ons

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Available Packages

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

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Available Add-Ons

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Additional Vespa

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

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Learn to Vesping Ride Course: 1 driver

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

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Learn to Vesping Ride Course: 2 drivers

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

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Learn to Vesping Ride Course: 3 drivers

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

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Shuttle to/from train station/airport

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

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Travel Insurance Quote

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

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Travel Concierge

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.

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

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

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

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

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Day 5B - Ride to Peccioli & Piaggio

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

Contact Us

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Vesping Around

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.

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