Wine Tasting by Scooter: the 15 Best Rides

1.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours · from $144 per scooter (seats 1)Our pick

Leave Florence by minivan for Chianti’s quiet back roads, where you can ride an original 50cc Piaggio Vespa, electric Vespa, Piaggio Zip, or Fiat 500 Topolino. Guides such as Niccolo, Julia, Heather, and Yo have led recent departures. Expect a safety lesson, medieval villages, vineyard views, a winery visit, wine and olive oil tasting, and a Tuscan meal.

“Absolutely incredible experience! Niccolo and Julia were amazing guides. You get a little tutorial to learn how to ride the Vespa and then you get to ride the Vespa around Chianti with beautiful views for about 2 hours! The included lunch and wine were great.”

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2.Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads

★★★★★★★★★★5.0 · 614 reviews · 5 hours (approx.) · from $228Top rated

From central Florence, guides such as Luca, Alexa, and Dejan take you by air-conditioned minivan to a family winery in the Chianti Rufina hills. After a Vespa lesson, you ride country roads past vineyards and villas, tour the cellar, and finish with Tuscan food, wine, and estate olive oil.

“Okay, in short this was probably the BEST experience of the entire trip. All 6 of us recommend whole heartedly. Go on this tour!!! TLDR: The food, the views, the tour, the service, the people - all fantastic and top notch. Learned about wine, learned how to ride safely and tested everyone before going out, and ate a delicious lunch at the most beautiful winery!!! FULL REVIEW: Alright, we were traveling as an adult family which can always be challenging when it comes to planning things to do. We had two 60 year olds, 2 in their 30s and 2 in their 20s and EVERYONE loved this experience!! First, let…”

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3.Tuscany Vespa Tour from Florence with Wine Tasting

★★★★★★★★★★5.0 · 425 reviews · 7 to 8 hours (approx.) · from $241

Spend seven to eight hours riding a Vespa through the Tuscan hills, visiting San Gimignano, and sharing a light lunch with local wine. Guides such as Daniel, Cecilia, Giacomo, Marco, and Stefano help beginners practice safely, take photos, and enjoy the day. You need an original driving licence and must be at least 18 to drive.

“The vespa tour was the best experience! It was my first time on a vespa and our guides were the best teachers. Once on the road I realized that the drive was just magical, the hills of Tuscany were breathtaking and covered with vineyards and castles We stopped in San Gimignano to walk around this medieval town and then off to wine tasting and dinner at another wonderful destination with views and a sunset! Guides were the best! Hands down favorite tour to date!”

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4.Small Group Vespa Tour Tuscany Winery & Lunch

★★★★★★★★★★4.9 · 268 reviews · 7 hours · from $235

You’ll leave Florence by van, learn to ride a Vespa on quiet country roads, and follow the hills to San Gimignano. Guides such as Lorenzo, Cecilia, Daniel, and Mido help nervous riders feel safe. After gelato and free time in town, you’ll enjoy a generous Tuscan lunch and local wine at a scenic winery.

“If you’re thinking about booking this tour, do it! We spent a wonderful day with our tour guide, Cecilia. First, she picked us up in Florence and took to us to Piazzale Michelangelo to enjoy the beautiful view. Then, we made our way to pick up the vespas. The Vespa ride through the Tuscan hills to San Gimignano was incredible and so much fun! We made some stops along the way for photo ops. In San Gimignano we had some time to explore the town. Finally, we dropped off the Vespas and Cecilia drove us to the wine tasting and lunch. Of course, the wine tasting and lunch menu were…”

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5.From San Gimignano: Tuscany Vespa Tour, Lunch & Wine Tasting

★★★★★★★★★★5.0 · 147 reviews · 6 hours (approx.) · from $180

Meet Tuscany on Wheels near Poggibonsi and spend about four hours riding a 50cc automatic Vespa through Chianti. Guides such as Ottavio, Alessandro, Lorenzo, and Vincenzo lead the route, photo stops, and winery visit. Expect a Tuscan meal, three wines, olive oil, and a required driving test before departure.

“Alessandro was a great guide on this adventure. We saw spectacular views and he gave us a nice history of what we were seeing. Riding a Vespa is super exciting and fun, and he made sure we were always safe.”

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6.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168

Spend about six and a half hours riding a Vespa through the Chianti hills near Siena. Follow a guide past vineyards, olive groves, Monteriggioni, Castellina, and Radda, then stop at Casale dello Sparviero for a winery visit, wine tasting, and light lunch. You may ride yourself or sit behind an escort, but drivers must pass a safety test.

“This tour was fantastic, and our guide, Mathilde, was awesome and made the day great. The only problem we had was that Mathilde discouraged us from taking 4 vespers like we had reserved and instead going as couples on 2 vespers. The cost of which is significantly lRead more”

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7.Small-Group Tuscany Vespa Tour with Lunch & Wine

★★★★★★★★★★4.5 · 95 reviews · 7 hours (approx.) · from $204

Ride a 50cc automatic Vespa through the Chianti hills near San Gimignano, stopping for photos before a winery lunch, wine, and olive oil tasting. You need real scooter experience, a valid license for Italy, and confidence on public roads. Small groups are limited to seven Vespas, with guides such as Alessandro, Vincenzo, Emma, and Domenico.

“Be aware that the tour does not offer hassle free hotel pick up as stated in the description. You must meet them at the Porta Roma. From there you go on a 45 minutes long van ride to the companies office for 2 hours of paper work and safety tests before you get on a Vespa. The guide was not mean and a little off putting, but definately would not say he was fun or engaging. And be warned that the tour starts and stops on very busy city traffic streets with several round - a- bouts to navigate and we even seemed to be on a highway within a…”

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8.Florence/Badesse: Tuscany Group Vespa Tour with Wine Tasting

★★★★★★★★★★4.4 · 56 reviews · from $123

Spend four hours riding an original automatic Vespa through Tuscany’s Chianti Hills, with stops in Castellina in Chianti and at a scenic winery. An Italian and English-speaking guide leads the route, and you may ride yourself or travel with a local driver. Bring a license, credit card, closed shoes, and confidence on two wheels.

“We had a great time. The ride was stunning. The bikes were great. The winery visit was fun and the food excellent. I'd go it again!!”

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9.Tuscany Vespa Tour with Lunch & Wine

★★★★★★★★★★4.8 · 54 reviews · 7 hours · from $210

You’ll ride your own automatic 50cc Vespa through quiet Chianti roads near San Gimignano, with a test ride, guide-led stops, and a family-run winery lunch with wine and olive oil. Guides such as Vincenzo and Emiliana are praised for patient coaching and lively local stories. Previous scooter experience and an Italian-valid driver’s license are required.

“Fabulous! We learned how to ride the Vespa then did an amazing tour around the area for a full experience! The stops along the way were fun, and the stories our guide shared were engaging! Our final stop at the winery was very intimate, and we felt welcomed by the family & staff while we enjoyed good food and good wine. Highly recommend!!!”

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10.Evening Fiat 500 and Vespa Prosecco Tour

★★★★★★★★★★5.0 · 34 reviews · from $146

Ride through Rome after dark with a driver-guide in a classic Fiat 500 or Vespa, stopping at the Colosseum, Baths of Caracalla, Pyramid of Cestius, Aventine Keyhole, and Janiculum Hill. Guides such as Roberto, Cesare, and Simon add history, photos, and local tips before a prosecco toast at Fontana dell’Acqua Paola.

“Tour was great. Guide/driver was comical and accommodating. We had a fantastic time and the vintage car got so much attention.”

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11.Florence Vespa Tour as a Passenger, max 6 people + Wine Window!

★★★★★★★★★★5.0 · 32 reviews · 1 hour 30 minutes (approx.) · from $114

Let a professional Vespa chauffeur handle Florence’s roads while you enjoy Piazzale Michelangelo, Fiesole, San Miniato al Monte, city landmarks, and a final stop at the Orcagna wine window. The 90-minute tour is in English, limited to six people, and offers afternoon or evening departures.

“Definitely the highlight of our time in Florence! My husband (he’s a big dude) was a little nervous at first. But the professionalism, communication, and joy of the experience had him smiling and having fun in no time! An absolute must do!”

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12.Vespa – Wine and Photography service in Rome

★★★★★★★★★★5.0 · 32 reviews · 1h 30m · from $61Best value

Ride behind a Vespa driver through central Rome, stopping at the Colosseum, Orange Garden, Trastevere, and Gianicolo Hill. You receive wine at the hilltop and 25 Sony Alpha 7 IV photos. English, Italian, and Turkish guides lead groups of up to 10. Guides may include Jacob, Busu, Kaya, Karim, or Abbas.

“Tour was the perfect way to end my trip to Rome! Love the way the pictures came out :)”

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13.Around Florence Hills: App‑Guided e‑Vespa Tour + Wine&Food

★★★★★★★★★★4.8 · 26 reviews · 4 hours · from $99

Pick up an electric Vespa on Borgo Ognissanti and follow a multilingual phone app through Florence, Fiesole, and up to Piazzale Michelangelo. This is a self-drive outing for experienced scooter riders, not a guided tour. Your four-hour rental includes helmets, insurance, and a Tuscan wine-and-food tasting in Oltrarno.

“Nous avons aimé - la liberté de circuler à son rythme - les informations en français sur nos Tél - la disponibilité du loueur de vespa”

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14.Around Florence Hills: App‑Guided e‑Vespa Tour + Wine&Food

★★★★★★★★★★4.5 · 22 reviews · 4 hours (approx.) · from $100

Spend four hours on an electric Vespa, following a smartphone app from central Florence to Fiesole, Piazzale Michelangelo, and San Miniato al Monte. You finish with Tuscan wine, cold cuts, and cheese in an Oltrarno food bar. Previous scooter or motorcycle experience, an international driving licence for some nationalities, and a €900 card deposit are required.

“The manager was extremely helpful. Be careful because the gos route guide may run down phone battery before getting back. Multiple drivers should use one phone at a time”

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15.Vespa Tour as a Passenger + Wine Window!

★★★★★★★★★★5.0 · 17 reviews · 1.5 hours · from $141

Sit behind an experienced driver and see Florence by classic Vespa, from the Duomo and Ponte Vecchio to Piazzale Michelangelo and Fiesole. This small-group ride includes a helmet, insurance, fuel, and a wine window. Guides such as Diego, Riccardo, Alex, and Giovanni lead tours in English or Italian.

“Riccardo was an incredible guide. This activity is one of the best unique ways to see Tuscany ! I 100% recommend this activity to anyone ! Riccardo is such a friendly, helpful and informative guide!”

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