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Tuscany by Vespa | Getaway

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  • Location: Italy
  • Duration: 6 Days/5 Nights
  • Departing from: Florence at 9:30 a.m.
  • Tour finishes: Siena bus or train station, any time this morning
  • Departures 2020: May 3, 17 & 31, June 7, 14 & 28, July 12, Aug. 23, Sept. 6 & 20, Oct. 4, as well as private departures
  • Price 2020: €2,350 per person based on double occupancy and minimum 6 people. €2,550 for 2–5 people. Single supplement: €200. Pillion passengers receive €100 discount.

We designed this trip for those who want (or need!) a quick and fun adventure. We pick you up from enchanting Florence and then transfer you into the countryside to meet your guide and your Vespa™ scooter. You will soon be cruising along Chianti’s quiet roads, gliding past vineyards and villas. No need to worry about where to go and what to see because your guide will lead the way! They know the most scenic roads, the loveliest places, and the best food and wine in Tuscany. Touring by scooter is a wonderful way of exploring Tuscany. You can stop when and wherever you want and parking is never a problem. Combine the freedom and exhilaration of touring by scooter with the amazing food, wine, and beauty of Tuscany.

** We can transform any of our Tuscany Vespa tours into a special Culinary & Wine departure, with wine tastings, cooking lessons, and some special lunches. If you want more, and are at least four in your party, we are happy to extend the tour for you by adding on extra days.

Scooterbella® in the news: our tours have been featured in the travel section of The Guardian (UK), Jan 20th, 2007. Another article was published by The Observer on April 23rd, 2006. Our Tuscany scooter trip was also featured in a 3-page full-color article in the London Telegraph, and in London’s The Times.  Book this trip! Send us an email

The Scooters – We provide 125cc Vespa™ scooters. They are lightweight, comfortable, and easy to ride. They have an electric start and automatic transmission, and the brakes are on the handle bars, like on a bicycle. We provide you with helmets. 

NOTE: A motorcycle license is NOT required to drive a scooter a 125cc scooter in Italy. A valid car license is required.

SCOOTER SAFETY & REQUIREMENTS - PLEASE READ CAREFULLY!!

To drive a scooter, you must be over 18 years of age & have a valid driver’s license. Previous experience driving a scooter or motorbike is essential. You must arrive at the start of the trip already a competent rider, otherwise the risk of injury and hospitalization is too great. If you have not ridden a scooter before then you should take lessons or rent a scooter locally and learn how to ride it before coming on the trip.

Please note: We will not teach you how to drive a scooter. You must arrive at the start of the trip already a competent rider.

You will be driving a motor vehicle on public roads. You are responsible for your safety but also for the safety of other motorists, bikers and pedestrians. You must be able to control the scooter and drive it competently. If we feel your driving skills put you and others at risk, we reserve the right to take the scooter away from you. In the event that you cannot ride as a passenger on the back of someone else’s scooter then we will help to arrange an alternative mode of transport such as a taxi or a rental car, but at your expense.

By making a booking, you declare to have a driving licence valid for the duration of the journey and for the vehicle used on this tour.

Tuscany by Vespa | Getaway itinerary

Day 1 – Sunday: Pick-up in Florence, Brolio Castle, Radda in Chianti


The tour picks up at 9:30 a.m. from the Hotel Orto de’ Medici, our recommended hotel in Florence. You can fly directly into Florence or Pisa, which is just an hour away by bus or train. We then have a 1hr 15 min transfer to the little hamlet of San Sano. After a safety talk and a little bit of practice to get our Vespa legs, begin your ride past the hilltop towns of I Bossi and San Felice. Wonderful views over the heart of Chianti take in a string of medieval castles. Stop in the medieval "borgo" of Castagnoli and enjoy a delicious lunch at their elegant restaurant, then continue your ride to Brolio Castle where we have a fascinating visit. Brolio has been home to the noble Ricasoli family since 1141 and also houses the famous Baron Ricasoli winery. Our afternoon ride takes you to the charming hilltop town of Radda in Chianti, where the four-star hotel Palazzo Leopoldo will be your home for the first two nights. Dine tonight at a local trattoria. Overnight Radda. Transfer from Florence, hotel and dinner included.

Day 2 – Monday: Chianti Classico Ride


This morning you ride west towards the hilltop village of Castellina in Chianti where you have time to walk along the ancient vaulted street which was part of the medieval fortifications. You'll have time to peruse boutiques and shops before hopping back on your Vespa for a super scenic ride amongst the rolling olive groves and vineyards of Chianti Classico fame. Stop for a coffee break in the village of San Donato before continuing on to Panzano for lunch at a small family-owned winery. The setting is truly magnificent as you look out over a patchwork of vineyards, olive groves, and forests adorned with stone villages, farm houses, and villas. The afternoon unfolds with a ride to the Badia a Coltibuono to visit the ancient abbey. You'll see the ageing cellars built at the time of the monks, the gardens, courtyards, cloisters, and frescoed rooms narrated by expert guides. Return to Radda and relax at the hotel spa or enjoy a superb gelato from “Antica Gelateria.” We reconvene for an aperitivo and then dine in a lovely restaurant in town. Overnight Radda. Hotel, breakfast, lunch and dinner included.

Day 3 – Tuesday: San Gusmé and the Crete Senesi

The ride today takes us along quiet backroads lined with olives trees and through chestnut forests to the highest point in Chianti for breathtaking views. We then drop down to the village of San Gusmé, which has been inhabited since the 8th century. A short walk around the medieval walls rewards you with gorgeous views over a sea of vineyards. Then ride south into a completely different terrain as we leave the green wooded hills of Chianti for the wide-open spaces of the Crete Senesi. Those who have seen the films “Stealing Beauty” or “The English Patient” will recognize this starkly beautiful landscape of barren rolling hills topped by stone farmhouses and solitary cypress trees. Stop for lunch at a famous local trattoria in the lovely hamlet of Chiusure. After lunch, ride to the walled village of San Quirico d'Orcia and check into the Villa del Capitano, your home for the next two nights. Tonight’s dinner is in the garden courtyard at a local trattoria. Overnight San Quirico d'Orcia. Hotel, breakfast and dinner included.

Day 4 – Wednesday: the Orcia Valley, Montepulciano, and Pienza

Today we have a gorgeous ride through the wonderful Orcia Valley, where you’ll see the iconic rolling hills famous from postcards and calendars. Take small roads that wind their way up, over, around, and between tiny villages such as Monticchiello, where we’ll stop for a stroll and a coffee break. Then ride for another hour or so to the hilltop town of Montepulciano, renowned for its Vino Nobile wine. You have time to explore the city's colorful streets and Renaissance palazzi, do a bit of shopping, and then stop for lunch at one of the many restaurants. Afterwards, ride to the perfect Renaissance town of Pienza, which was designed and built by a local boy who made it big: Pope Pius II, who decreed that his home town was to become a center of art and humanistic scholarship. It was completely rebuilt between 1459 – 1462 according to the latest Renaissance styles. You then have a leisurely ride back to your lovely hotel in San Quirico. Take in the views while enjoying a glass of wine before dinner at a restaurant just a short hop from your hotel. Overnight San Quirico d'Orcia. Hotel, breakfast, and dinner included.

Day 5 – Thursday: the Gothic city of Siena

Our last ride takes us along one of the most scenic roads in Tuscany, just past the ancient walled village of Asciano. Eventually you reach Siena, where you'll drop off your trusty Vespa and head into the historical center. Siena's Gothic architecture was left perfectly preserved after the city was taken over by Florence in 1585, and its main square, “Il Campo,” is considered by many to be among Italy’s finest. Enjoy lunch in town and then learn all about the famous bareback horserace known as "il Palio" from our local guide, who will also take us to visit the cathedral and its medieval treasures. You have free time this afternoon to explore Siena's colorful shops and backstreets, and also time to rest at our hotel before enjoying a final dinner together in town. Overnight in Siena in a centrally located superior three-star hotel. Breakfast, dinner and hotel included.

Day 6 – Friday: end of trip

Depart at your leisure this morning. The bus station is an 8-minute walk from the hotel and you can get buses to Florence (departing every hour, the journey takes 1 hr 15 mins) or Rome (3 hrs). For rail connections, you can get a taxi to the train station, which lies a few kilometers outside of the city center. Breakfast included.

Note on Itinerary: Although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control, such as the weather

Trip Cost Includes: 5 nights accommodation (4 nights at four-star hotels, 1 night at a comfortable three-star in Siena), 5 breakfasts & dinners + 1 lunch; bilingual guide; *provision of a 125cc Vespa™ scooter with rear carrier bin and helmet; related third party liability insurance as required by Italian law (but not insurance covering damage to the scooter caused by you); fuel; van pick-up on Day 1 from Hotel Orto de' Medici in Florence (you and your luggage); bag transfers throughout the trip; entrance to the park and gardens of Brolio castle; guided visit of Siena with licensed city guide and entrance to the cathedral.

Booking: e-mail us at info@scooterbella.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend "Travel Guard" to our North American clients, just click on the logo below.  Australian, New Zealand, and British travelers, please consult your insurance brokers.

We look forward to having you join us for the trip of a lifetime!

* Vespa™ is a trademark of Piaggio, SpA

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Getting There: make your way independently to Florence to meet your group at 9:30 a.m. at the Hotel Orto de’ Medici for a one-hour van transfer to pick up our scooters in the Chianti countryside. We’d be happy to book your a room at the Orto if you arrive the night before, or you can simply store your luggage there and explore the city if you arrive that morning.

Air: The closest airport to the trip is Florence, but you can also fly into Pisa, which receives many low-cost flights from around Europe and is only an hour away by bus or train (see the airport websites for more information).

Rail: Eurostar and the new Italo high-speed trains connect Florence with Milan (travel time about 3 hours), Bologna (travel time 35 minss) and Rome (travel time 1 hour 35 minutes). See our Transport Information page for detailed information about the Italian train system and relevant airports.

Getting Away at the End of the Trip: the trip ends on Friday morning in Siena. You can take a bus from the city center directly to Florence (the Florence bus station is right next to the train station, in the heart of town), and the trip takes 1 hour 15 mins. There are also buses to Rome (3 hrs), or you can take a taxi to the train station, located just outside of town, for rail connections. Should you require an earlier departure we can arrange a private transfer (at your expense).

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

4.90/5
RatingRatingRatingRatingRating 
4.90 out of 5
Ratings based on 18 Verified Reviews

Average ratings
4.9
Guides
5.0
Quality of itinerary
4.9
Food quality & variety
4.7
Value for money
4.9
Right amount of activity
5.0
Overall satisfaction

Reviews
5
by John and Julie Stubbs
Posted Sep 16, 2019

Our guide was absolutely superb....she brought Tuscany to life for us in many ways. Her passion and knowledge of the area was outstanding. Organisation and execution of the whole tour was exemplary. Would highly recommend . Thank you.

5
by Tom H and Silvia V
Posted Jul 07, 2019

My wife and I had a terrific time. Tuscany is stunningly beautiful (we were there in early June). The itineray, the food, the quality of the operation are terrific. Rachele is a great guide and new friend .. charming, competent, and knowledgeable.I agree with another reviewer .. don't do this until you feel quite comfortable on a scooter or motorcycle. The roads in Tuscany are a lot curvier then I expected. My wife rode as a passenger and this proved quite challenging for me. (She had a grand time on back smile)Highly recommended.. thanks Rachele and Brett and rest of team.

5
by Silvia
Posted Jul 07, 2019

What a special way to see Tuscany! Everything about the Vespa tour was awesome! My husband & I loved our Guide Rachele who was with us the whole time! The intinerary was perfect! We enjoyed our time with Brett (the owner)! We highly recommend Scooter Bella!

5
by Dordane N.
Posted Jul 01, 2019

We did a two week trip to Italy, the first week on our own, the second week with ScooterBella. The scooter tour was hands down the BEST part of our trip. The hotels they had us at were beautiful and comfortable, in gorgeous little towns. The daily agenda was a nice balance of activity, sight seeing, riding, food and down time. The guides really made the experience special by giving advice on menus, wines and the cool local features. They were very attentive to the groups wants and needs and constantly asked for feedback and what we preferred to do. They even hosted several evening pre-dinner cocktail gatherings including a wonderful wine tasking session. If anyone ever asks for a recommendation, I would totally point them to ScooterBella. Wonderful communication and highly service oriented. A note to American travelers, do make sure you are comfortable riding through the hills and tight curves. It seemed like many of us overestimated our skills and riding through the tight curves with local traffic was a little scary at first. They ride single line in Italy, not staggered. Just make sure you take the question seriously when the tour company asks you to rate your skill level. You shouldn't do this trip unless you are a skilled rider. As for everything else, truly a great outfit these guys run. Thank you Brett and team. Such wonderful memories.

4.8
by Susan L
Posted Jun 29, 2019

I can't imagine a better way to see Tuscany. Our guides did an amazing job of translating and providing historical & cultural context for what we saw, heard and tasted. They introduced us to charming places I likely would not have found on my own.

4.8
by Deb S
Posted Jun 25, 2019

Absolutely best way to see Tuscany!!! Fabulous!

5
by Darren S.
Posted Jun 23, 2019

We just completed our 4-day scooter tour around the Chianti region in early June 2019. Wow, what a fantastic experience! We had a total of three weeks in Italy and enjoyed the entire experience.....but when the 6-person group was pressed to rank their 3,2,1 favourites for the holiday the scooter tour was the resounding favourite. The itinerary was perfect, the accommodation spot on, the restaurants unforgettable and the guides with their knowledge, energy and sense of fun made the whole experience one that we have been raving about to all our friends since returning home. Thank-you to Brett and Sara for putting it together and HUGE thanks to Claire, Manuela and Rachelle for bringing it all to life. We will never forget the time we enjoyed with you and we hope to do some Custom Walks (or cycling!) again in future.

5
by Wendy from Auckland
Posted Dec 02, 2015

Our Scooterbella tour of Tuscany, based at exquisite Fontebussi and with our superb guides, Sara and Marco, far exceeded all expectations. Any preliminary anxiety was quickly dispelled by the outstanding professionalism of the whole experience. Our safety and enjoyment was paramount to Scooterbella and consequently we had one of the best adventures of our lives. The beauty of Tuscany is unparalleled and we saw it at its best. We look forward to another experience with you in the future.

5
by Terry from Auckland, New Zealand
Posted Nov 03, 2015

Our Vespa tour through the lanes and villages of Tuscany was the highlight of our European tour. Our guides Sara and Marco from the outset were engaging, interesting and a whole lot of fun and every day exceeded the last. Our accommodation was fabulous, our itinerary varied and interesting and the food and wine was outstanding. To be able to ride through the Tuscan countryside with a warm breeze in your face and smelling the grapes from harvest was a very special experience. We're already planning our next Scooterbella experience !

5
by B Crawford from Auckland, New Zealand
Posted Aug 23, 2015

Tuscany by Vespa - everything you imagined and more. Once again Sara and Marco made the trip something we will always remember. Already planning our next scooter trip with Scooterbella. The best and most knowledgeable guides, off the beaten track highlights, fantastic food and wine - like us - you will go home and talk about this trip for years to come.



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