Vespa & Sidecar Tours in Rome: 15 Days Out That Repay the Slot

1.Florence Vespa Tour: Tuscan Hills and Italian Cuisine

★★★★★★★★★★5.0 · 4,019 reviews · 6 hours (approx.) · from $78Our pick

Follow guides such as Leo, Chris, Ado, or Gabriel from Florence into the Tuscan hills on an automatic Vespa. After a safety test, stop at San Miniato al Monte, pass Galileo’s former home, and eat bruschetta, pasta, cheese, salami, and wine at a country estate. A Fiat alternative may be available if you cannot ride safely.

“Leo…our guide is excellent!! What a way to see the hillsides of Florence - on a Vespa!! Leo was very knowledgeable and extremely likeable!! Lunch was very good in a picturesque spot! Definitely recommend. 5* experience around!! Thank you”

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2.Vespa Sidecar Tour By Night with Pickup

★★★★★★★★★★5.0 · 1,803 reviews · 3 hours (approx.) · from $146

Ride through Rome with a professional driver and guide, stopping at Piazza Venezia, the Colosseum, Aventine Hill, Trastevere, and Janiculum Hill. You will share a sidecar Vespa with one other person, or ride behind the driver. Gelato and coffee are included, and guides such as Manuel, Roberto, Andrea, and Simone bring local stories and humor to the three-hour route.

“Such a fun way to see Rome! One person on the back of the Vespa and one in the side car-you see the main highlights in a fun and efficient way to travel the city. Our guide was great fun and super knowledgable. We had a blast!”

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3.Rome Morning Vespa Sidecar Tour in Rome with Cappuccino

★★★★★★★★★★5.0 · 1,771 reviews · 3 hours (approx.) · from $163

Ride through Rome with a professional driver while your guide narrates by headset. Visit Trevi Fountain, the Pantheon, Piazza Navona, St Peter’s Square, the Colosseum and more, with a cappuccino and cornetto break, photo stops and Pantheon entry included. Guides such as Claudio, Matteo and Luca are known for lively storytelling.

“It was such a fun experience. Amazing tour!! The tour guide was very knowledgeable about the city. My son and I had a lot of fun riding on the Vespa. An absolute must do if you visit Rome. I recommend 100%.”

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4.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125

Leave Florence by minivan for a safety briefing and a scenic Vespa ride through Chianti. Stop in villages and at viewpoints, then visit a winery for cellar touring, Tuscan lunch, wine, and olive oil. Choose a single or double Vespa, or drive a Fiat Topolino e-car. Guides may include Yo, Lorenzo, Ela, or Haider.

“This is a such fun way to see the countryside. Our guides were amazing. Their knowledge of local traffic laws made it easy to just follow their directions. We enjoyed a great pasta lunch and wine tastings. Definitely recommend.”

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5.Rome Vespa Scooter Tour with Professional Photographer

★★★★★★★★★★5.0 · 857 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $66

Ride as a passenger on a chauffeured Vespa through central Rome while a professional photographer captures your visit. Stops include the Colosseum, Circus Maximus, Orange Garden, Mouth of Truth, Pantheon, Castel Sant’Angelo, and Gianicolo Hill. Guides such as Eric, Leo, Yaqub, and Jesus are praised for friendly service, safe riding, and helpful commentary.

“We had a great time seeing the sites especially the cannons. Our guides were real troopers as it was cold and rainy. I highly recommend this tour!”

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6.Highlights Vespa Sidecar Tour with Coffee and Gelato

★★★★★★★★★★4.9 · 747 reviews · from $141

Ride through Rome with an English- or Spanish-speaking guide and professional Vespa driver. Visit the Colosseum, Aventine Hill, Pyramid of Cestius, Trastevere, and Janiculum Hill, stopping for coffee or tea and gelato. The three-hour route mixes famous sights, quieter corners, photo stops, and easy city views without wearing out your legs.

“The tour covered many lesser known highlights about Rome. It was massive fun with a knowledgeable guide and experienced riders to provide a safe and enjoyable adventure. Highly recommend.”

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7.Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine

★★★★★★★★★★5.0 · 719 reviews · 6 hours (approx.) · from $160

Take the wheel of an original 1960s Fiat 500 on a guided half-day drive from Florence. After a manual-gear test, follow guides such as Ado, Chris, Leo, or Alex through hillside roads, stop at San Miniato al Monte, and share a Tuscan lunch with regional dishes. Expect a small convoy, radio contact, and limited space inside the tiny cars.

“It was awesome. We loved it all. Tall people may struggle but there is an electric car option available. If sitting a third person in the back seat, it is quite tight!”

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8.Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

★★★★★★★★★★5.0 · 660 reviews · 4 hours (approx.) · from $139

Take the wheel of a restored 1960s Fiat 500 and follow your guide from Scandicci into the Chianti hills. After practice with the manual gearbox, you will drive in convoy to a 15th-century villa and wine estate for tastings and a light lunch of Tuscan meats and cheeses. Guides such as Bella and David add local insight.

“David was a great guide for this tour, spoke English perfectly and was very friendly. He gave a quick rundown on how the cars work at the start. It was only brief though so please believe the tour summary when it says you need previous experience driving a manual/stick shift car. There are a few cars with the regular manual transmission, and then a few with the double clutch system- this is more complex and you should probably only choose one of the double clutch cars if you’ve had prior experience with that before so you don’t damage the gearbox. We chose Topsy, she was a 1967 model. After our…”

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

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

Leave Florence by air-conditioned minivan for a classic Vespa ride through the Chianti Rufina hills. After a safety lesson, follow guides such as Alexa, Luca, or Dejan past vineyards, olive groves, and villas. Finish at a family-run winery with cellar tour, wine, olive oil, and Tuscan lunch. A passenger option is available if riding feels unsafe.

“So fun! Luka is the champion sommelier in Italy and was a fabulous host. We ended up doing the tasting after test driving the vespa and realizing the curvy roads were not a good match with our skills. A great experience overall!”

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10.Rome Vespa Tour with Professional Photoshoot

★★★★★★★★★★5.0 · 576 reviews · from $81

Ride through Rome as a passenger on a Vespa driven by a professional guide such as Elmar, Eric, or Gennaro. The 90-minute route passes the Colosseum, Circus Maximus, Orange Garden, Piazza Venezia, Castel Sant’Angelo, and Janiculum Hill, with a photographer taking 20 professional photos per person.

“The tour was amazing! You guys should try. Its a must. booked it in a short notice and they accommodated us. Safe and worth the penny! 5star seevice”

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11.Tuscany Vespa Tours Through the Hills of Chianti

★★★★★★★★★★5.0 · 515 reviews · 6 hours (approx.) · from $193

Leave Florence with guides such as Ben, Filippo, Alessio, and Leonardo for a safety-led Vespa ride through Chianti. After about two hours on the road, sit down at a Tuscan villa or castle estate for lunch, wine, and extra virgin olive oil tasting. A valid driver’s license is required.

“We did this excursion on our honeymoon and it’s been a highlight of our trip! The tour guides were very professional and safety was their top priority when getting us ready to ride! They ran a tight ship and thought of every detail. Actually riding the Vespas was a thrill, and the views while riding were amazing! The scenic stops were great, and the guides gave great information on each thing we saw! The lunch was substantial and the wine & olive oil were great! 10/10 experience I would recommend to everyone!”

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12.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 classic Vespa through the Tuscan hills, exploring San Gimignano, and sharing a light Tuscan lunch with local wine. Guides including Daniel, Cecilia, Giacomo, Marco, and Stefano help beginners practice, ride safely, or travel as a passenger. Drivers need an original license and must be at least 18.

“Bejon, Marco and Sam were amazing. We had the absolute best day. Nothing will ever top our experience. Special thanks to Sam for making it extra special.”

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13.From Florence: Small Group Vespa Tour Tuscany Winery & Lunch

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

Leave Florence by van for a small-group Vespa ride through quiet Chianti roads. After a lesson, ride toward San Gimignano for a guided visit and gelato at Dondoli, then enjoy a Tuscan lunch and local wine tasting at a scenic winery. You can ride with a guide if you prefer not to drive.

“Mehdi was amazing…he was informative when explaining the day and events, attentive at all times, supportive regarding the Vespas, absolutely enjoyed his company during lunch! Vespa Dream ✅”

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14.Self-Driven Sightseeing Tour by Vespa

★★★★★★★★★★4.9 · 240 reviews · from $130

Ride a Vespa through Rome with guides such as Vittorio, Fabio, Marco, or Francesco. In three hours, you can visit the Colosseum, Pantheon, Trevi Fountain, hilltop terraces, and lesser-known corners, with the route adjusted to your interests. One Vespa is provided per two participants, and you must be at least 18 with the required driving documents.

“Massimo was the best ever. Learned more and enjoyed more places than expected. The Vespa driving experience in Rome was invigorating.”

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15.Countryside Vintage Fiat 500 Driving Tour

★★★★★★★★★★4.8 · 232 reviews · 5 hours · from $153

Drive a restored 1960s Fiat 500 from Florence into the Tuscan hills with an English-speaking guide. After a hands-on briefing, follow the convoy along cypress-lined roads, stone-walled lanes, and olive groves. Stop at an old church and scenic overlooks, then enjoy Tuscan ham, cheese, and Chianti on a private terrace. Manual driving skills are required.

“An unforgettable Florence experience — driving a vintage Fiat 500 through the Tuscan hills. A privilege to take the wheel of such an icon — truly a must-do!” Thank you to Cristiano & Leo who were a brilliant double act and made the trip!”

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