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Cruise Tuscany’s iconic Chianti hills in a vintage car, visit top local wineries, and savor a vineyard lunch that showcases the region’s best wines and flavors. This intimate five-hour tour offers both scenic beauty and authentic Tuscan hospitality.
Cruise Tuscany’s iconic Chianti hills in a vintage car, visit top local wineries, and savor a vineyard lunch that showcases the region’s best wines and flavors. This intimate five-hour tour offers both scenic beauty and authentic Tuscan hospitality.
Book with Tuscany on Wheels
Verified experiences and guided adventures in the surrounding area.
Operated by Tuscany on Wheels · Cipressino, Toscana
Set against the rolling hills of Tuscany’s Chianti region, the Chianti in Maggiolone tour invites travelers to step back in time aboard a classic vintage car, winding through some of Italy’s most celebrated wine country. This five-hour journey begins in Cipressino, a tranquil town in the heart of Toscana, where the landscape is defined by undulating vineyards, olive groves, and medieval hilltop towns. It’s the perfect playground for wine lovers and cultural explorers eager to taste authentic Tuscan flavors amid shimmering cypress-lined roads and panoramic vistas.
Your local guide welcomes you at Tuscany on Wheels before setting off on this unique adventure, where the magic is in both the destination and the ride. The gently purring vintage Maggiolone (Volkswagen Beetle) crisscrosses the scenic routes near San Gimignano, known for its towering skyline and Vernaccia white wine. Two intimate winery visits are included, each offering a rich dive into DOCG-certified wines. The first stop is a boutique vineyard that specializes in Vernaccia, where you learn the nuanced wine-making process and enjoy a tasting that brings the crisp regional whites to life.
The tour’s second winery is a family-run estate recognized for its Chianti Classico and Brunello di Montalcino, alongside renowned Super Tuscan blends. Here, a passionate vintner leads a guided tasting of up to nine Tuscan wines, balanced with rare balsamic vinegar aged for over three decades and exceptional truffle-infused extra virgin olive oil. This immersive tasting hones your palate, deepening appreciation for Tuscany’s famed agricultural heritage.
After savoring the varietals, the journey culminates in a romantic lunch right in the vineyard, surrounded by neatly lined grapevines swaying in the Tuscan breeze. This al fresco meal highlights local ingredients and traditional recipes that celebrate the region’s flavors, making each bite a sensory extension of the tour.
Chianti in Maggiolone stands out for its blend of classic style, intimate group size, and genuine connection to local culture through wine and food. Unlike mass-tourism winery visits, this tour feels personal and educational, appealing to travelers seeking a richer understanding of Tuscan viticulture and countryside life. Whether you’re a seasoned oenophile or simply chasing a scenic escape, this classic car wine tour pairs adventure, history, and taste to create an unforgettable Tuscan experience.
Yes, round-trip transportation in a vintage Maggiolone is included, so you won't need to drive.
A leisurely lunch in the vineyard is part of the experience, featuring local Tuscan dishes.
Up to nine Tuscan wines are sampled, including Chianti Classico, Brunello di Montalcino, and Super Tuscans.
Please notify the tour provider in advance to discuss any special dietary needs.
Guests must be at least 18 years old to participate due to alcohol tasting.
Currently, tours are given in English and Italian.
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