THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover Tuscany’s stunning Chianti region aboard a vintage Ape Calessino. This customizable tour offers panoramic views, local insights, and a charming way to explore rural Italy at your own pace.
Discover Tuscany’s stunning Chianti region aboard a vintage Ape Calessino. This customizable tour offers panoramic views, local insights, and a charming way to explore rural Italy at your own pace.
Book with Tuscany on Wheels
Verified experiences and guided adventures in the surrounding area.
Operated by Tuscany on Wheels · Cipressino, Toscana
Experience the heart of Tuscany like never before with the Custom Tour: Ape Calessino, a charming way to explore the iconic landscapes of this famed Italian region. Operating out of Cipressino, a quaint Tuscan village steeped in rustic charm, this tour offers a unique chance to traverse the Chianti hills aboard a classic Ape Calessino – a three-wheeled vehicle beloved for its vintage character and nimble handling on narrow country roads.
The base tour lasts for two hours, during which you'll glide through panoramic vistas of rolling vineyards, olive groves, and cypress-lined lanes that define the Tuscan countryside. Guided by a knowledgeable local, you'll gain insider perspectives on regional culture, history, and agricultural traditions, bringing Tuscany’s famed landscapes vividly to life. The flexibility to extend your experience up to six hours allows you to customize your route, adding stops like artisan wineries or medieval villages, tailoring your journey to match your adventure spirit.
What sets this tour apart is not just the destination but the mode of transport: the Ape Calessino offers a distinctive blend of nostalgia and intimacy with the surroundings. Unlike large tour buses, this vehicle allows for an immersive sensory experience—the scent of wild herbs, the warmth of the Tuscan sun, and unobstructed views that invite spontaneous photo stops and quiet moments.
Cipressino itself is a tranquil gateway to Tuscany’s rich outdoor recreation. Its location in the Chianti region makes it an ideal base to explore not only Tuscan landscapes but also local food and wine culture, art, and historic villages. The roads you’ll travel after departing Cipressino wind past Renaissance estates, ancient castles, and vineyards producing world-renowned Chianti Classico wines.
The Custom Tour: Ape Calessino is particularly well suited to travelers seeking intimate, flexible experiences away from crowded tourist routes. Whether you’re a couple, a small group of friends, or solo adventurers, this ride lets you set your pace while uncovering the quiet corners of Tuscany’s outdoor allure.
This tour is a stand-out in Tuscany’s extensive offering for its low-impact approach to exploring nature and culture combined. The exclusive use of the vehicle, included gasoline, and attentive accompaniment by your guide ensure a smooth and safe outing. Ideal for spring through fall, this experience blends adventure, relaxation, and local discovery into one unforgettable Tuscan day.
easy.
2–6 hours.
Minimal physical exertion required; suitable for all fitness levels comfortable with sitting and occasional short stops.
The minimum age for participants is 18, so the tour is designed for adults only.
Yes, the base tour is two hours but you can add experiences up to a six-hour customized adventure.
The vehicle is used exclusively by your group, ensuring a private and personalized experience.
The base tour includes the vehicle and guide only; additional stops such as wine tastings can be added upon request.
Guides are local experts and typically fluent in Italian and English, ensuring clear communication for international visitors.
Booking at least a few days in advance is recommended to secure your preferred date and customization options.
The Chianti region has been a center for winemaking since the 13th century, shaping the landscape and culture seen on this tour.
This tour emphasizes low-impact transport and supports local businesses to maintain the region’s ecological and cultural balance.
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