THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Drive a restored vintage Fiat 500 through the rolling hills and villages of Tuscany with Tuscany on Wheels. Discover a hands-on way to immerse yourself in Italy’s celebrated landscape and culture.
Drive a restored vintage Fiat 500 through the rolling hills and villages of Tuscany with Tuscany on Wheels. Discover a hands-on way to immerse yourself in Italy’s celebrated landscape and culture.
Book with Tuscany on Wheels
Verified experiences and guided adventures in the surrounding area.
Operated by Tuscany on Wheels · Cipressino, Toscana
Situated along Strada di Sant' Appiano in Barberino Tavarnelle, Tuscany on Wheels offers a distinctive way to navigate the Italian countryside—behind the wheel of a restored vintage Fiat 500. This isn’t just a car rental; it’s a retro adventure through one of Italy’s most iconic regions, where history, culture, and landscape converge in vivid, tangible ways.
Barberino Tavarnelle lies in the heart of Tuscany’s rolling hills, an area defined by patchwork fields of vineyards, olive groves, and medieval villages. The region is celebrated for its gentle contours shaped by centuries of cultivation and its timeless beauty sculpted by human hands and natural processes. Driving a classic 1973 Fiat 500 here allows adventurers to move at a pace that invites attention to every detail—the terra-cotta rooftops, the rustic stone walls, and the vibrant wildflowers lining country roads.
Tuscany on Wheels specializes in providing meticulously restored Fiat 500s, boasting manual transmissions that call for an engaged driving experience. Rentals include 80 kilometers and personalized route suggestions, highlighting lesser-known hilltop towns, artisan wineries, and panoramic vantage points that reveal the iconic Tuscan landscape. Whether used for romantic day trips or leisurely independent journeys, this unique offering connects travelers more intimately with the region than conventional tours typically allow.
The company’s location provides easy access from Florence, making it an attractive option for visitors looking to complement their city stays with an authentic countryside excursion. The vintage 500s here stand out not only as vehicles but as symbols of Italy’s rich automotive and cultural heritage—a perfect match for Tuscany’s enduring charm.
For outdoor and adventure travelers eager to pair scenic drives with meaningful local experiences, Tuscany on Wheels offers a stylish, slow-motion alternative to the high-speed nature of modern touring. Here, the road itself becomes part of the adventure, revealing Tuscany’s historic soul with every turn.
easy.
up to 8 hours.
Suitable for any physical condition; mainly seated driving with light walking for stops
Renters must be at least 21 years old with a valid driver’s license.
Yes, rentals include 80 kilometers; additional mileage may be arranged in advance.
A valid Italian or international driver’s license and a credit card for the deposit are required.
Yes, roadside assistance comes with every rental for peace of mind during your drive.
Yes, Tuscany on Wheels offers picnic baskets and wine tasting options upon request.
In case of dangerous weather, you can reschedule your rental or receive a voucher valid for 12 months.
Tuscany’s hill towns grew around medieval fortresses and monasteries, showcasing a layered history dating back to Etruscan times.
This area supports sustainable tourism with efforts to preserve its agricultural landscapes and reduce vehicle emissions while using classic cars.
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