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.
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
Meeting point
You’ll meet your escort and group at Via San Giovanni, one of the most iconic streets in San Gimignano.
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.
Chianti hills scenic ride
Cruise through the rolling hills of Chianti, past vineyards, olive groves, and sunflower fields. The scenery is pure postcard Tuscany.
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.
Winery tour
Arrive at a family-run winery and join a guided visit through vineyards and production areas, learning how Chianti wines are made.
For Reference Only. Itineraries are subject to change
Select participants and date
Start times are in the product’s local time
Wed, 28 Jan 2026
...
...
4.93
113 Ratings
5
109
4
2
3
0
2
2
1
0
Logan Z.
Verified Review
November 01, 2025
Peaceful Hill Escape
Jay N.
Verified Review
November 01, 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.
Verified Review
October 14, 2025
Aadya X.
Verified Review
October 08, 2025
Unforgettable Vespa Tour
Samuel M.
Verified Review
October 05, 2025
We had a wonderful experience!! The highlight was definitely the ride through Chianti and the delightful wine!
Scenic Ride Bliss
Moritz L.
Verified Review
October 02, 2025
Loved, loved this Vespa trip! The views, the food, and the relaxed pace made it a day to remember. An authentic local experience for a change.
Elijah W.
Verified Review
October 02, 2025
Amazing Chianti Drive
Aditya K.
Verified Review
September 29, 2025
Better than I had expected. Driving down quiet roads with olive groves was like magic. The wine tasting afterwards was just yummo and true.
Ultimate ride
Isabella J.
Verified Review
September 26, 2025
The Vespa was easy to handle and scenic route through the Chianti hills was gorgeous, the lunch at the winery was truly authentic & delicious!!I really enjoyed the ride & food. 10/10 would recommend this tour!!
Anton W.
Verified Review
September 26, 2025
Beautiful Day Adventure
Ben I.
Verified Review
September 23, 2025
The countryside was lovely. Riding freely down open roads gave me the most marvelous travel experience. Lunch at the winery was fresh, savory, and quaint.
Authentic and Fun
Nikhil H.
Verified Review
September 20, 2025
This tour is simply the best in Tuscany-Good wine and the stunning scenery of San Gimignano!!
Siddharth H.
Verified Review
September 20, 2025
Worth it!!
Eva G.
Verified Review
September 17, 2025
Really enjoyed the tour our guide Beatrice was very knowlegeble and informative! The wine and olive oil tasting was a treat. Definitey a must when visiting the city!!
Ride And Relax
Noah F.
Verified Review
September 14, 2025
The perfect mix of enjoyment riding and peaceful sightseeing. The small group made it feel like a personal experience, and every stop was masterfully arranged. Highly recommend it.
Harper G.
Verified Review
September 14, 2025
Breathtaking & Delicious
Ashwin D.
Verified Review
September 11, 2025
The Vespas were fun, the scenery was unreal and the lunch with local wine was so chill and authentic!!
Tuscany Dream Ride
Aiden C.
Verified Review
September 08, 2025
I have gone on many tours, but this was unique. The Vespa creates a feeling of freedom you can't find on a bus. Every stop had something beautiful.
Max C.
Verified Review
September 08, 2025
Scenic Road Views
Zoe B.
Verified Review
September 05, 2025
Every turn delighted me with postcard views. I loved the easy pace of country living. The hilltop lunch was home-cooked perfection.
Top Notch experience
Clara W.
Verified Review
September 02, 2025
The tour & experience was 10/10 - scenic, well-paced and totally authentic!!
Arpit T.
Verified Review
September 02, 2025
Absolutely Magical
Jakob U.
Verified Review
August 27, 2025
The tour was incredible!! The Vespa ride offered stunning countryside vistas before arriving at San Gimignano!! The vineyard wine tasting was authentic & delicious!!
Great Local Experience
Rumi T.
Verified Review
August 21, 2025
The tour was genuine and real. No tourist mayhem, just fine people, lovely roads, and excellent wine. The perfect half day spent.
Pure Magic
James S.
Verified Review
August 15, 2025
The Vespa ride was worth it but the wine tasting and views over San Gimignano were simply divine! Our guide was fantastic & shared local insights!!
