This tour is part of a broader initiative to bridge American and Italian Vespa culture celebrating the scooter lifestyle not just as a means of travel, but as a vehicle for connection. Each itinerary is carefully curated to explore local traditions, cuisine, and people while creating opportunities to meet and ride with passionate Vespa clubs across Italy. A new region will be spotlighted each year, offering participants a deeper cultural immersion and a unique way to experience Italy—from the saddle of a classic scooter.
Riding skills: 🔴 Advanced
For experienced riders ready for a challenge.
These routes include narrow mountain roads, switchbacks, steeper climbs, and busier traffic zones—often with fast-moving cars and assertive local drivers. You must be able to confidently share the road with multiple forms of transport and respond quickly to changing conditions.
Ideal for expert riders who are agile, alert, and used to adapting to dynamic environments.
Embark on an unforgettable 10-day Vespa journey through the heart of Sicily, designed in collaboration with the local Vespa Clubs which will be meeting the itinerary group. This itinerant adventure begins and ends in Taormina, weaving through iconic landscapes and historic towns like Bronte, Enna, Caltagirone, Modica, Noto, and Catania. Along the way, riders will experience the raw beauty of Mount Etna’s slopes, the baroque splendor of southeast Sicily, and the warm hospitality of local Vespa clubs joining for scenic rides, meet-ups, and shared dinners.
Each day is crafted to blend cultural immersion with the joy of riding. Highlights include a boat tour of Isola Bella, pistachio tastings in Bronte, a ceramic workshop in Caltagirone, a hands-on ricotta-making experience near Ragusa, and a chocolate tour in Modica. The tour also features select culinary stops, coastal detours, and charming village visits—all culminating in a coastal ride back to Taormina. With a perfect balance of adventure, tradition, and local connection, this journey captures the spirit of Sicily one winding road at a time.
For experienced riders ready for a challenge.
These routes include narrow mountain roads, switchbacks, steeper climbs, and busier traffic zones—often with fast-moving cars and assertive local drivers. You must be able to confidently share the road with multiple forms of transport and respond quickly to changing conditions.
Vespa is a Piaggio trademark, Vesping Around is not associated or affiliated in any way
2 x 24/7 Tour Leaders: Mauro the founder of Vesping Around, and Giovanni from the DC Vespa Club
Accommodation: 9 nights at a High End Boutique Hotel
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.
Specified Meals: all breakfasts, all lunches & dinners
Vespa: Rental, helmet, top case, third-party insurance, unlimited gas
All Planned Activities: Cave museum, boat tour, half day cooking lesson, as per program
Travel Kit: Includes backpack, water canteen, rain jacket and pants, commemorative sticker and patch
Exclusive Services: Travel Insurance, Travel Concierge
A Lifetime Experience!
Airfaire to Catania (CTA) the closest airport
Train: Train service from/to accommodation. You will want to arrive at the Taormina.
Travel Insurance: This is required for every traveler in order to keep your booking confirmed. Vesping Around recommends Faye.
International License: Required to ride in Italy. We are happy to handle the administrative tasks required to obtain your International License Permit for you.
ETIAS VISA: Required to enter EU Countries starting 2026
All stays are to be confirmed closed to trip departure. A day-by-day itinerary will be shared with all participants at the latest 60 days before departure.
Mini Hotel Wf2 Caltagirone in Caltagirone offers family rooms with air-conditioning, balconies, and private bathrooms. Each room includes a work desk, free toiletries, and a mini-bar.
Distance to ride: – | KM: ~5
Approx time on saddle: ~30 mins
Vespa assignment and safety briefing
Light orientation ride to build confidence with the vehicles and local traffic patterns
Welcome dinner
Distance to ride: – | KM: ~5
Approx time on saddle: ~30 mins
Morning
Beach time at a hand picked location in Letojanni
Lunch
Lunch in Savoca at the iconic Godfather "Bar Vitelli"
Afternoon
Taormina exploration:
Ride to Porta Catania
Coffee stop at Piazza Belvedere
Narrow medieval alleys
Visit to Ancient Roman Theatre
Photo stop at White Lotus San Domenico
Evening
Dinner in town
Night ride back to the hotel
Distance to ride: ~70 km via Etna’s northern slope
Approx time on saddle: 2 hrs
Breakfast
9:00 AM – Departure
Visit to the Alcantara Gorges (walking and steps time required)
Closed-toe shoes recommended
This location has a number of steps to hike (elevator should be available TBC)
Time to relax at natural river beaches (1–2 hours)
Lunch
Stop at local "Agriturismo", typical farm-to-table restaurant
Afternoon
Hotel check-in
Pistachio workshop near Bronte
Evening
Dinner at the hotel
Distance to ride: ~60 km through interior highlands
Approx time on saddle: 1hr 45 mins
Breakfast
9:00 AM – Ride departure
10:30 AM – Stop in Centuripe (Big Bench panoramic stop)
Snack break
Lunch
Stop in Agira
Agriturismo lunch stop
Famous dessert to try "Cassatina di Agira"
Afternoon
Visit to Castello di Lombardia
Vespa Club Enna welcome ride (TBC)
Hotel check-in
Group ride with Vespa Club Enna (TBC)
Painted mug workshop
Evening
Dinner at a traditional trattoria
Distance to ride: ~75 km through rural Sicily
Approx time on saddle: 1 hrs 30 mins
Breakfast
9:00 AM – Departure
11:00 AM – Arrival in Caltagirone
Hotel check-in
Midday
Ceramic workshop (approx. 2 hours)
Lunch at local hand-picked farm to table high end restaurant
Afternoon
Free time to explore Caltagirone and its famous ceramic staircase
Evening
Light "apericena" (happy hour drink with light finger food)
Distance to ride: ~80 km
Approx time on saddle: 2 hrs
Breakfast
9:00 AM – Departure
Visit to WWII Bunker (82nd Airborne Division Monument)
Lunch & Experiences
Stop at Donnafugata Castle
Wine tasting and lunch
Ricotta and lunch experience near Ragusa
Afternoon
Arrival in Modica
the chocolate city
Free time until dinner
Evening
Dinner at the hotel
Distance to ride: ~45 km
Approx time on saddle: 2 hrs 30 mins
Leisurely ride through Baroque towns
Ride around the south heel of Sicily, up to the Spiaggia dei Due Mari where you can see the Ionian and Mediterranean seas meeting
Lunch in Marzamemi, a charming fishing village
Gelato stop in Noto
Distance to ride: ~90 km coastal route
Morning winery visit in Avola
Scenic coastal detour to Fontane Bianche for a quick swim
Stop in ancient borgo of Ortigia in Siracusa
Dinner in Catania
Distance to ride: ~60 km coastal ride north
Meet & greet with Vespa Club Catania, joint evening ride
Explore Catania’s historic center with guided tour and lunch
Ride up the scenic Riviera dei Ciclopi
Arrive in Taormina
Farewell dinner with sea view + final toast with club friends
Distance to ride: – | KM: ~5
Leisurely breakfast
Farewells, gear return, transfer assistance
Pricing starts at: $5,450 pp
Payment: $2,000 deposit + 3 Installments
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!
Also available i select locations 310cc models
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.
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.
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.
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