Wine by Vespa: the 12 Best Tasting Rides

1.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours Our pick

Leave Florence by minivan for a guided ride through Chianti’s quiet roads. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. Stop in medieval villages, visit a winery, taste wine and olive oil, and enjoy a Tuscan meal. Guides such as Niccolo, Julia, Heather, and Yo help first-time riders feel at ease.

“The trip was beautiful! I will start with saying, have a small breakfast or snack before because lunch is around 2. It’s a great way to meet people and enjoy the sights. Dinner was phenomenal, the guide was so educated and the lessons for vespas were incredibly thorough. We opted for the car because of the weight between the two of us on the vespa but the car was so cute and so fun to drive it was still a blast! Have fun, be kind, and enjoy the gorgeous trip they lay out for you. We’d gladly go again, 10/10 recommend”

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

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

Leave Florence by air-conditioned minivan for a family-run winery in the Chianti Rufina hills. After Vespa practice, follow guides such as Luca, Alexa, or Dejan along country roads, then tour the cellar and share a Tuscan lunch with wine and estate olive oil. Riders who feel unsure can ride as passengers.

“Riding Vespas thru the country roads of small town Tuscany is a blast. It's a bit dangerous because you're riding with real traffic along winding and hilly roads, but there's no shame in opting to ride as a passenger instead. We started with a tour of the winery, then got a 10-15 minute moto riding lesson, then went on the 20-25 minute Vespa ride with Alexa. Then we returned to enjoy wine and delicacies at the Tuscan vineyard. It's a great way to spend half a day in Tuscany.”

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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 7 to 8 hours riding a Vespa through the Tuscan countryside, with practice time, a visit to medieval San Gimignano, and a local winery lunch with Chianti. Guides such as Daniel, Cecilia, Giacomo, and Stefano are praised for patience and good humor. You need an original driving licence and must be at least 18 to drive.

“Amazing tour of the beautiful Tuscan region with a stop at the incredible city of San Gimignano…all while riding vespas!!! SO MUCH FUN! Final top off was lunch and vino for everyone! This was our best highlight of Florence and a must-do!”

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4.Small Group Vespa Tour Tuscany Winery & Lunch

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

Leave Florence by comfortable transport, learn to ride a Vespa on quiet Tuscan roads, and follow the hills to San Gimignano. You will have time for gelato and sightseeing before a winery lunch with local wines. Guides such as Lorenzo, Daniele, Cecilia, and Mido are praised for patience and safety. Passengers can ride with a guide or use the tuk-tuk option.

“The Vespa tour guide was a great way to see the Tuscan area and the wine country. Midos was our tour guide. He was great! We were a group of 5 couples. We all had a chance to learn how to use a Vespa. The staff was great. Everyone did fine. I decided to ride with Midos because I wanted to take pictures and Videos. My husband rode by himself. We stopped by a vineyard to take pictures. The grapes grown here were San Giovese, just beautiful! We went through the country side and stopped by San Gimignano area where we shopped and strolled around this wonderful town, then We…”

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

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

Meet near Poggibonsi, learn the ropes, then follow your guide through Chianti vineyards, olive groves, and medieval villages on an automatic 50cc Vespa. The day includes scenic stops, a winery visit, Tuscan lunch, three wines, and olive oil tasting. Guides may include Ottavio, Alessandro, Lorenzo, or Vincenzo.

“Such an amazing day. Our guide was great and very knowledgeable. The sights were exactly what you’d picture Italy to be and lunch was off the charts. The winery we visited was amazing, the host was super funny, food was tasty and the curated wine superb. Don’t leave Tuscany without giving this a try.”

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6.Vespa Tour with Lunch&Chianti Winery from Siena

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

Ride a Vespa through the Chianti hills on a guided convoy from Siena, passing Monteriggioni, Castellina, and Radda. Stop at Casale dello Sparviero for a winery visit, tasting, and light lunch. You may drive if you have solid scooter experience, or ride as a passenger. An international driving permit and credit card are required for drivers.

“Riding behind my husband on the Vespa was a fun experience. He has experience of driving a motorcycle so he adapted well. Another guest who said they drove Vespas previously was denied driving one on the excursion due to safety concerns. We only stopped in 2 villages and 1/2 the ride was on beautiful country roads and the last 1/2 of the tour was in industrial areas. Wine tasting was not worth the stop. Two glasses were given to taste, both reds, and no tour of the winery itself. If it wasn't for the idea of getting lost, it makes more sense to rent a Vespa and tour the countryside…”

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

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

You’ll ride an automatic 50cc Piaggio Vespa through Chianti’s vineyard roads, with photo stops, views toward San Gimignano, and a generous winery lunch with wine and olive oil. Guides such as Alessandro, Vincenzo, Emma, and Domenico lead the small groups. Previous scooter experience is required, and the driving test is serious.

“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

You’ll ride an automatic Vespa through Chianti with an English or Italian-speaking guide, stopping in Castellina in Chianti and at a scenic winery. Choose to drive or ride as a passenger, taste local wine, enjoy dry snacks, and photograph Tuscany’s farms, vineyards, castles, and parish churches.

“Everything was great! Francisco was an excellent teacher and guide!”

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9.Tuscany Vespa Tour with Lunch & Wine

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

Trade Florence’s streets for quiet Chianti roads on a 50cc automatic Vespa. After paperwork, a safety briefing, and a driving test, you’ll ride past vineyards, olive groves, cypresses, and medieval villages near San Gimignano. A local winery serves lunch, wine, and extra virgin olive oil. Guides have included Vincenzo, Emiliana, Lorenzo, and Dom.

“Vincenzo was absolutely amazing and incredibly knowledgeable/passionate about his tour. The Vespas were in excellent condition, the views were picturesque, and the “light” food and wine were delicious. I would very happily do this again!”

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

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

Ride behind a professional Vespa chauffeur on a 90-minute outing for up to six people. You’ll see Florence from Piazzale Michelangelo, Fiesole, San Miniato al Monte, the cathedral, and the oldest bridge, then finish at a historic wine window. Guides such as Diego, Alexa, Giovanni, and Dan have led past tours.

“Highlight of my trip! This was a fun way to see the outskirts of Florence and end with a beautiful scenic view of the city. It was a lot of fun and I highly recommend”

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11.Vespa – Wine and Photography service in Rome

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

Ride behind a professional driver through central Rome, stopping at the Colosseum, Orange Garden, Trastevere, and Janiculum Hill. You will receive 25 Sony Alpha 7 IV photos, a helmet, and a wine tasting at the hilltop stop. Guides speak English, Italian, and Turkish. Ask who is driving your departure, with past guides including Jacob, Busu, Kaya, Karim, Abbas, and Eric.

“AMAZING!!! Jacob, Busu, Kaya were wonderful, knowledgeable and fun!”

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

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

Follow an app-guided route from Borgo Ognissanti through Florence’s hills, Fiesole, and Piazzale Michelangelo on an electric Vespa. You set the pace, use your phone for directions and audio commentary, then finish with Tuscan wine, cheese, and cold cuts at a Food & Wine Bar in Oltrarno. Scooter experience is required.

“Tour was excellent. The most beautiful views. The restaurant at the end of the tour was closed but we were given a great sandwich suggestion and that was 5 stars as well. Very pleased with the women and man that assisted us for setting up and turning in.”

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