Chianti Vespa Tour from San Gimignano with Wine Tasting and Lunch

Ride through the hills of Tuscany on a vintage scooter, visit a local estate and enjoy a local meal

4.93 (113) ·

Travel Flexibly

· 7.50h · San Gimignano, Italy

Chianti Vespa Tour from San Gimignano with Wine Tasting and Lunch

Exploring Chianti on your own sounds dreamy until you're lost, stressed, and stuck with tourist traps. Skip the hassle and ride like a local on this small-group Vespa tour from San Gimignano. With a professional escort leading the way, you’ll zip through scenic countryside, stop for wine tastings, tour a working winery, and enjoy a long lunch in the hills. No GPS, no guesswork, just pure Tuscan joy.

What You Get With This Tour

Friendly, English-speaking escort
Chianti countryside
Original Vespa scooter rental
Fuel and helmet
Guided winery visit
Wine tasting of local wines
Traditional Tuscan lunch
Scenic ride with photo stops
Group size of 15
Tour guide gratuities
Hotel pickup and drop-off

Tour Itinerary

1

Meeting point
You’ll meet your escort and group at Via San Giovanni, one of the most iconic streets in San Gimignano.
2

Vespa orientation and safety check
Before departure, your escort will show you how to safely operate the Vespa. You’ll get comfortable with the controls and route before setting off.
3

Chianti hills scenic ride
Cruise through the rolling hills of Chianti, past vineyards, olive groves, and sunflower fields. The scenery is pure postcard Tuscany.
4

Photo stops in the countryside
Stop for panoramic photos at one of the most scenic overlooks on the route—think endless vineyards and winding cypress-lined roads.
5

Winery tour
Arrive at a family-run winery and join a guided visit through vineyards and production areas, learning how Chianti wines are made.
6

Wine tasting
Taste a selection of wines, including Chianti DOCG and other regional varietals. Learn what makes them unique and how to pair them.
7

Tuscan lunch
Sit down for a traditional countryside lunch paired with house wine.
8

Ending point
The tour concludes at the same location where it began. You’re free to continue exploring the historic center or relax after the ride.

Additional Information

Leave the crowds behind and start your day in San Gimignano, meeting your tour escort in Via San Giovanni, the main street that cuts through the heart of this iconic hilltop town. Here, you’ll be introduced to your Vespa, an Italian icon ready to take you deep into the heart of Tuscany. After a quick safety briefing and rental check, you’ll hit the road in a small group, riding through rolling hills, olive groves, and rows of cypress trees. The ride is smooth and scenic, with plenty of photo-worthy views along the way. You’ll stop at a local winery for a guided visit and a proper Tuscan lunch, with wine tasting included. After the experience, you’ll ride back to the starting point, with your head full of views and your heart full of Chianti.

Chianti Vespa Tour with Wine Tasting and Lunch Description

Your 7.5-hour small group tour includes:

Professional tour escort
Original Vespa scooter rental (automatic)
Fuel and helmet
Scenic ride through the Chianti countryside
Visit to a medieval village
Guided tour of a local winery
Wine tasting of regional wines
Traditional Tuscan lunch at the winery
Group size of 15

San Gimignano meeting point

Your experience starts in Via San Giovanni, San Gimignano, just steps away from the town’s famous towers. After checking in and meeting your escort, you’ll receive your Vespa and all necessary equipment. Drivers must show a valid license and credit card and be able to confidently operate the scooter. If you’re not comfortable driving, a shared Vespa option is available—or you may be offered an alternative vehicle if available.

The ride through Chianti

There’s no better way to explore Tuscany than on two wheels. Your route winds through some of the most breathtaking parts of the Chianti region, known for its vineyard-dotted hills, stone farmhouses, and postcard-perfect landscapes. You’ll pass by sunflower fields, olive groves, and small medieval villages, with stops for photos and to soak it all in. This is the kind of ride where the journey really is the destination.

Visit to a winery

Midday, you’ll stop at a historic Chianti winery surrounded by vineyards. A guide will walk you through the winemaking process and into the cellars where the magic happens. Learn how the region’s famous wines are made—Chianti DOCG, Super Tuscan blends, and more—and taste them for yourself.

Tuscan lunch

After your tour, sit down for a relaxed lunch overlooking the countryside. Expect traditional dishes like pecorino cheese, cured meats, fresh pasta, and seasonal vegetables, all paired with house wine. A vegetarian option is available upon request. It’s not a tourist meal—it’s a real Tuscan table.

Return to San Gimignano

With full bellies and satisfied smiles, you’ll ride back to San Gimignano along scenic roads. The tour ends at the same meeting point in Via San Giovanni, leaving you free to continue exploring the town or simply head home with your helmet full of memories.

Customer Reviews

4.93 (113)

Leave a review

Logan Zhu, 01 November 2025

Peaceful Hill Escape

Jay Norton, 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 Zhou, 14 October 2025

Aadya Xu, 08 October 2025

Unforgettable Vespa Tour

Samuel Mcbride, 05 October 2025

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

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Frequently Asked Questions

What to bring?

A valid international driver’s license is required. Please also bring along a credit card to guarantee your rental. Closed-toe shoes, sunscreen and sunglasses are also recommended.

Is there any chance my tour might be canceled?

In case of extreme weather, the tour may be modified or canceled for safety reasons. You’ll be offered an alternative or a refund.

Is this tour run by The Tour Guy?

No, this tour is operated by one of our trusted and vetted partners in Tuscany.

What if I have concerns about my ability to drive the Vespa?

All drivers must have experience operating a scooter. If the staff believes you’re not confident or safe, they may reassign you as a passenger or, if available, offer an alternative like a tuk-tuk or Fiat 500.