Experience the magic of Italy’s Prosecco region on a 4-day ride adventure starting in Vittorio Veneto, where each day blends scenic rides with rich cultural encounters and local flavors. From exploring the UNESCO-listed hills of Valdobbiadene and tasting world-class Prosecco, to visiting historic villas, medieval castles, and alpine malghe for hearty mountain meals, this itinerary captures the essence of slow travel. Evenings return you to the comfort of your boutique base for relaxed aperitivi and dinners in welcoming local osterie, making this the perfect journey for those seeking beauty, connection, and the real Italy—one ride, one bite, and one village at a time.
This trip's riding Skill Level: Il Viaggiatore (Intermediate)
“I’m comfortable riding on rural roads and can manage traffic calmly.”
and
This trip's riding Skill Level: Il Guidatore Esperto (The Expert Rider)
"I've owned or regularly ride scooters/motorbikes and love long rides."
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
Rental: helmet, cell-hone holder, third-party 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 if you don't have one.
All Planned Activities: everything included as per itinerary below
Travel Kit: Backpack, water canteen, rain jacket and pants, commemorative merch
Exclusive Services: access to 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.
We will take quick afternoon welcome ride to explore the immediate surrounding of the area and get confidence with our vehicles
During dinner, we will welcome our group and review what's in store over the coming week!
Today’s ride unfolds across the iconic Strada del Prosecco, tracing the vine-covered ridgelines between Refrontolo and Combai—quaint hilltop villages at the heart of the UNESCO-designated Prosecco Superiore DOCG region. A scenic stop at a local vineyard such as Ca’ Salina or Cantina Fasol Menin offers an intimate tasting of the area’s prized sparkling wines, surrounded by panoramic views of rolling hills. Guests continue on to Osteria senz’Oste, a self-serve culinary gem where lunch is enjoyed picnic-style among the vineyards. In the afternoon, the journey dips into the artistic grandeur of Villa Barbaro in Maser, a Palladian masterpiece adorned with Veronese frescoes, before arriving in the refined town of Asolo for a well-earned gelato beneath the gaze of its hilltop fortress. The return to Vittorio Veneto passes through Pederobba and Farra di Soligo, offering golden-hour vineyard views, and concludes with an apericena at Enoteca Castrum—an elegant wine bar nestled within the castle walls of Serravalle.
Easy day and visit to nearby medieval gem Monteriggioni.
Visit of historic San Gimignano
combai prosecco tasting in vineyard
lunch at local gourmet hidden gem
Visit of Villa Maser, Villa Barbaro
Gelato break in one of top Italian borgo: Asolo
Ride back via stunning roads along Pederobba and Farra di Soligo
Apericena in beautiful local castle
Day three begins with a short ride to the Grotte del Caglieron, a geological marvel of sculpted rock canyons and wooden walkways, where nature and centuries-old quarrying history meet. From there, the route flows through Cison di Valmarino, one of Italy’s most beautiful villages, known for its stone architecture and artisan heritage. Lunch is served at Frasca Marchet, a rustic farmhouse kitchen where local meats and cheeses take center stage. The afternoon is dedicated to a series of noble strongholds: from the still-inhabited Castello di Collalto to the grand Castello San Salvatore, once a strategic medieval fortress, and Castello di Collabrigo perched over Conegliano’s vineyards. The day winds down with gentle evening light casting shadows on Conegliano’s castle hill before returning to the hotel in Vittorio Veneto for a relaxed, light dinner. This day is a tribute to Veneto’s feudal past and natural beauty, told through its towers, caves, and timeless villages.
Caglieron Caves visit,
Visit of borgo Cison Val Marino
Gourmet picnic lunch
Visit of Castle Collalto, San Salvatore
Castle Collabrigo
Manzana
Conegliano
Light dinner hotel
Check out & Arrivederci!
For those extending their journey, Day 4 offers a breathtaking ride into the foothills of the Dolomites—a region where alpine culture meets Venetian tradition. The route begins with a glide around the turquoise waters of Lago di Santa Croce, a beloved local escape nestled between forested slopes. Riders then climb gently through the villages of Tambre, Lamosano, and Pieve d’Alpago, where narrow roads wind between mountain farms and pine-scented air. Lunch is hosted at Malga Coro, a rustic mountain dairy serving hearty alpine fare sourced straight from the surrounding pastures. The return ride sweeps through the Cansiglio Natural Park, one of Italy’s oldest and most enchanting forests, once reserved as royal hunting grounds for the Venetian Republic. Towering beech trees, hidden meadows, and sudden mountain vistas set the tone for a final apericena back in Vittorio Veneto—a satisfying close to an unforgettable detour into Veneto’s wilder side.
Santa Croce Lake
Tambre
Lamosano
Pieve d’Alpago
Spert
Lunch at typical mountain's Osteria (Malga)
Panoramic ride back through Cansiglio Natural park
Apericena in town with locals
Classico - Single Occupancy
Available until 30 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: $2,290
Deposit: $1,000
Classico - Double Occupancy
Available until 30 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: $1,780
Deposit: $1,000
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: $350
Deposit: $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
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.
Call or Text: 888 773 2910