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Drive a vintage Fiat 500 through Tuscany’s rolling hills, visiting handpicked wineries to sample Chianti wines and local delicacies. Join Tuscany on Wheels for an authentic small-group adventure in Barberino Tavarnelle.
Drive a vintage Fiat 500 through Tuscany’s rolling hills, visiting handpicked wineries to sample Chianti wines and local delicacies. Join Tuscany on Wheels for an authentic small-group adventure in Barberino Tavarnelle.
Book with Tuscany on Wheels
Verified experiences and guided adventures in the surrounding area.
Operated by Tuscany on Wheels · Cipressino, Toscana
Set in the heart of Tuscany’s renowned wine country, Tuscany on Wheels offers an immersive ride through rolling hills and iconic vineyards, departing from Strada di Sant' Appiano, 9/i in Barberino Tavarnelle. This unique adventure invites you behind the wheel of a vintage Fiat 500—a classic Italian car that perfectly complements the timeless landscape. Over five hours, you’ll trace winding backroads that snake through olive groves, cypress-lined lanes, and medieval villages, all while enjoying the perfect blend of scenic driving and localized viticulture insights.
The tour’s intimate design accommodates two travelers per car, fostering a personalized experience. The highlight lies in visits to two carefully selected local wineries, where you’ll savor up to seven varieties of Chianti-classic wines, alongside tastings of extra virgin olive oil and aged balsamic vinegar, products that define Tuscan culinary heritage. Beyond the tastings, knowledgeable guides delve into the region’s winemaking traditions and cultural background, providing depth to each sip.
What sets Tuscany on Wheels apart is its dedication to authenticity and intimacy: from the hands-on vintage driving experience to the small group size, ensuring each participant feels connected to the land and its stories. The tour culminates with breathtaking stops for photographers and wine lovers alike—hilltop viewpoints offering sweeping panoramas of vineyards stretching towards the horizon. Whether you’re drawn by classic Italian automotive charm, exquisite wine culture, or the striking rural vistas, this trip delivers a thoroughly distinctive way to engage with Tuscany’s outdoors and heritage.
Situated less than 30 kilometers south of Florence, Barberino Tavarnelle serves as a gateway to Tuscany’s famed Chianti zone, making Tuscany on Wheels a standout choice for travelers seeking more than just a drive, but an authentic cultural and outdoor leisure experience.
Yes, since the Fiat 500 is a manual transmission, basic experience is needed to operate it confidently during the tour.
Yes, wine tastings at two local wineries, along with samples of olive oil and balsamic vinegar, are included.
Tours are small and intimate, with two people per vintage Fiat 500 ensuring personalized attention.
Participants must be at least 18 years old to drive and join the tour.
No, travelers must arrange their own transport to Strada di Sant' Appiano, 9/i in Barberino Tavarnelle.
Yes, the vintage Fiat 500 is small with limited space, so it’s advisable to bring only essentials.
Tuscany on Wheels is a touring company based in Cipressino, Toscana, offering vehicle-based and culinary experiences across the Chianti hills and nearby towns such as San Gimignano and Siena. The business provides Vespa rentals (including helmets and maps), guided Vespa tours, vintage Fiat 500 experiences, tuk tuk drives, self-guided bike tours with picnic options, cooking classes, wine tours, and custom vehicle-based excursions. Tours listed include Chianti wine itineraries, Vernaccia tastings in San Gimignano, two-hour private tuk tuk drives combined with hands-on cooking at a local farm, and multi-stop day trips to Siena, Monteriggioni, Montepulciano, and Val d’Orcia. Many offerings combine scenic drives, winery visits, traditional Tuscan meals and guided or self-guided formats. Tuscany on Wheels operates a fleet that appears in its trip names: 50cc Vespas, vintage Fiat 500 cars, Ape Calessino vehicles, tuk tuks, and Vespa sidecars. The company lists options for self-guided rentals, guided afternoon and full-day tours, family-friendly wine-free options, and specialty experiences such as horse riding and cooking courses. Booking details, schedules and availability are provided per tour. The business highlights local producers and stops in historic towns, offering tastings and regional meals on several itineraries. Tuscany on Wheels is positioned for travelers seeking vehicle-based exploration of Tuscany from a base in Cipressino. Third-party reviews, booking platforms and tour listings provide additional guest feedback and practical booking information. Availability, durations and specific inclusions vary by tour; travelers should consult the tour listing for exact schedules, equipment included (helmets, maps, picnic menus) and any seasonal changes before booking.
Book with Tuscany on Wheels