Small Group Chianti Vespa Tour with Winery & Lunch from Certaldo

Savor tastings at a Tuscan farmhouse, plus make panoramic photo stops as you zoom by with a guide

4.93 (113) Travel Flexibly 7h Max 15 guests Max 15 Tuscany, Italy

Few things feel more Italian than riding a scooter through the vineyards of Chianti. This small-group tour lets you soak it all in from the back seat while an experienced driver handles the winding roads. Glide past olive groves, cypress trees and stone hamlets between San Gimignano and Siena, pausing for panoramic photos. Midway, visit two local wineries for guided tastings and enjoy a farmhouse lunch. It's the most fun way to experience Chianti's landscapes and flavors in a single day.

What You Get With This Tour

  • Chase the Tuscan sun on two wheels
  • Expert English-speaking guide
  • Classic 125cc scooter ride
  • Guided Chianti countryside tour
  • Wine tastings at 2 wineries
  • Traditional Tuscan lunch
  • Olive oil and balsamic tastings
  • Helmets and gloves
  • Small group experience
  • Guide tips

Tour Itinerary

  • 1

    Your tour begins in Certaldo

    Meet your guide in Certaldo, a medieval town between Florence and Siena, for a quick safety briefing. Settle onto your shared 125cc automatic scooter behind an experienced driver, then set off into the Chianti hills.
  • 2

    Ride through vineyards and olive groves

    Follow your guide along quiet country roads that wind through the heart of Chianti. Vine-covered slopes, silver olive groves, and cypress-topped hills roll past as you soak in one of Tuscany's most famous wine regions.
  • 3

    Pause for panoramic photo stops

    Next, pull over at scenic viewpoints where the Tuscan landscape opens up in every direction. Your guide shares stories about local culture and Chianti's centuries-old wine traditions while you capture the views.
  • 4

    Visit a family-run Chianti winery

    Then step off the scooter to tour a local winery tucked among the vines. Learn how regional wines are made using traditional methods, then sample a selection of Chianti reds straight from the estate cellar.
  • 5

    Savor a traditional Tuscan lunch

    Settle in at the winery for a relaxed farmhouse lunch. Start with antipasto of local cheeses and bruschetta, followed by a classic pasta dish, all paired with guided tastings of wine, olive oil, and balsamic vinegar.
  • 6

    Cruise back through the countryside

    After lunch, hop back on for a final loop through the Chianti hills. Wind past sleepy stone hamlets and rows of vines, making a last photo stop or two before the scooter heads back toward the base in Certaldo.
  • 7

    Your tour ends back in Certaldo

    By late afternoon, you'll arrive back in Certaldo where the day began. Say goodbye to your guide with a camera full of Tuscan views and the taste of Chianti wine still fresh in your mind.

Additional Information

Discover what to expect, what's included, and everything you need to know before booking.

Good to know:

  • Meeting Location: The meeting point is in Certaldo, about 20 minutes by car from San Gimignano. If arriving by train, Certaldo station is the closest and most convenient option.

  • Riding options: Ride as a passenger behind an experienced driver. Each 125cc automatic scooter is shared by two people.

  • Security deposit: A valid credit card is required for a pre-authorization deposit (prepaid cards, debit cards, and Amex are not accepted). It's released after the tour if there's no damage to the scooter.

  • Dress code: For safety, closed-toe shoes and long trousers are required. Flip-flops, sandals, and shorts are not permitted on the ride.

  • Alcohol consumption: This tour includes local wine. Participants consuming alcohol should be of legal drinking age in Italy (18). Please bring a government-issued ID if you plan to partake.

  • Dietary restrictions: Please contact us in advance with any dietary restrictions or allergies, so we can do our best to accommodate you.

  • Accessibility: Unfortunately, this tour is not wheelchair accessible. It is also not recommended for pregnant travelers or guests with serious medical conditions.

  • Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can depart on time.

Your tour includes:

  • Expert English-speaking guide

  • Shared 125cc automatic scooter with an experienced driver

  • Helmets and gloves

  • Guided ride through the Chianti countryside

  • Wine tastings at 2 local wineries

  • Traditional Tuscan lunch with olive oil and balsamic tastings

  • Small group experience

What to bring:

  • Government-issued ID

  • Closed-toe shoes

  • Credit card for the security deposit

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Free Cancellation
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Customer Reviews

4.93 (113)
Leave a review
Logan Z., 01 November 2025

Peaceful Hill Escape
Jay N., 01 November 2025

Vespa-ing across Tuscany was one for the record books. Hills rolling, warm breeze, and joyful friends. And topped off by wine tasting and local cuisine.

Jonas Z., 14 October 2025

Aadya X., 08 October 2025

Unforgettable Vespa Tour
Samuel M., 05 October 2025

We had a wonderful experience!! The highlight was definitely the ride through Chianti and the delightful wine!

Show more reviews

Frequently Asked Questions

Is this tour family friendly?

This tour is best suited to adults and older teens, since it involves riding a scooter and includes wine tastings. It's not recommended for pregnant travelers or guests with serious medical conditions.

What if I have concerns about my mobility on this tour?

Unfortunately, this tour is not wheelchair accessible, as it involves riding a scooter and moving over uneven countryside terrain. If you have concerns about your mobility, please contact us in advance to discuss your needs.

Do I need a driver's license?

You can ride as a passenger behind an experienced driver, so no license is needed to join. If you'd like to drive your own scooter, you must be at least 18 and carry a valid physical driver's license.

Is lunch included?

Yes, a traditional Tuscan farmhouse lunch is included. You'll enjoy antipasto with local cheeses and bruschetta, followed by a pasta dish, paired with guided tastings of regional wine, olive oil, and balsamic vinegar.

What should I wear?

For safety on the scooter, wear closed-toe shoes and long trousers. Flip-flops, sandals, and shorts are not permitted on the ride.

What if I have food allergies, intolerances, or other dietary requirements?

Please let us know at the time of booking. We’ll do our best to accommodate your dietary needs.

Start From: $148.75

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