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Ride through Chianti’s vineyards with Tuscany on Wheels, tasting Chianti Classico, Brunello, and Vernaccia before a stroll in historic San Gimignano. Discover the art and flavor of Tuscany’s winemaking tradition on this full-day guided tour.
Ride through Chianti’s vineyards with Tuscany on Wheels, tasting Chianti Classico, Brunello, and Vernaccia before a stroll in historic San Gimignano. Discover the art and flavor of Tuscany’s winemaking tradition on this full-day guided tour.
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Operated by Tuscany on Wheels · Cipressino, Toscana
Tuscany on Wheels delivers a crisp, authentic dive into the core of Tuscany’s celebrated wine country with its TOUR DEL VINO: Vernaccia & San Gimignano. This six-hour journey threads through the rolling hills of Chianti, a region famed for its sun-drenched vineyards and centuries-old winemaking traditions. Starting from Cipressino near Barberino Tavarnelle, you'll ride in comfort aboard a bus designed to whisk you away to two renowned family-owned wineries, each offering distinct, hands-on tastings designed to sharpen your palate and deepen your appreciation for Tuscan terroir.
At the first winery, the spotlight is on legendary reds like Chianti Classico and Brunello di Montalcino, alongside Super Tuscan blends and an exquisite 30-year aged balsamic vinegar. The producers here share craft secrets and tasting techniques, enriching your understanding beyond the usual sip. The tour then moves to a vineyard facing the iconic towers of San Gimignano, famed for the Vernaccia white wine, an elegant counterpart to the robust Chiantis of the region. This stop includes tastings of Vernaccia and Chianti Colli Senesi D.O.C.G., plus samples of truffle-infused olive oil.
After the winery visits, the tour winds down with a stroll through San Gimignano’s medieval streets, offering a window into Tuscany’s rich history with its uniquely preserved towers and vibrant piazzas. This stop enables a relaxed pace for visitors to absorb the atmosphere or enjoy a gelato before the return trip. With local guides providing insightful narration throughout, Tuscany on Wheels offers a well-rounded, accessible experience that suits wine lovers and cultural enthusiasts alike. The motto speaks volumes: “Think about drinking, we’ll handle the driving.”
This tour stands out as an exemplary taste of Tuscany’s outdoor lifestyle—where nature, heritage, and savor meet. It’s a must for anyone wanting to move beyond the typical and immerse in the flavors and landscapes that define one of Italy’s most iconic regions.
easy.
6 hours.
Suitable for most fitness levels with light walking on uneven ground and village strolls.
This tour is designed for adults due to wine tastings. Guests aged 14-18 are welcome but cannot participate in tastings.
Yes, you can request to finish the tour in San Gimignano instead of returning to the starting point.
Wear comfortable shoes for walking and bring a water bottle and light layers depending on the season.
Yes, the tour includes a free stroll through San Gimignano before heading back.
Up to nine different Tuscan wines are sampled across the two wineries.
Yes, Tuscan snacks are provided to complement the wine experience.
San Gimignano’s medieval towers date back to the 12th century and are a rare surviving example of urban defensive architecture in Tuscany.
Family wineries emphasize sustainable farming practices, with many focusing on organic viticulture to preserve soil health and biodiversity.
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