THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the historic charm of Cortona paired with the rich Syrah wines of Val di Chiana on a private, full-day tour. Enjoy a Tuscan lunch amid vineyards and olive groves far from the usual crowds.
Discover the historic charm of Cortona paired with the rich Syrah wines of Val di Chiana on a private, full-day tour. Enjoy a Tuscan lunch amid vineyards and olive groves far from the usual crowds.
Book with De Gustibus Tours
Verified experiences and guided adventures in the surrounding area.
Operated by De Gustibus Tours · Firenze, Toscana
Tucked within the undulating hills of Val di Chiana, just south of Florence, the historic town of Cortona offers an intimate tapestry of Tuscan life far from the typical tourist trail. De Gustibus Tours' Private Cortona and Syrah Under the Tuscan Sun is an eight-hour journey that stitches together wine, history, and the countryside’s raw charm into one immersive experience. This private tour delivers a nuanced glimpse into one of Tuscany’s best-kept secrets—its Syrah vineyards—and the enduring legacy of a town that has long inspired artists, writers, and wine lovers alike.
Cortona’s ancient stone streets lead you through a living museum of Etruscan ruins and Renaissance echoes, resting atop a hill nearly 500 meters high and overlooking the vast fertile valley below. The Val di Chiana is shaped by a microclimate and soil composition favorable for Syrah grapes, which local vintners have cultivated for decades, crafting wines that have garnered international acclaim. The sip of a robust Syrah here carries the earth, sun, and history in every bottle.
Beyond wine tasting, visitors will enjoy a traditional Tuscan lunch set against the backdrop of vineyards stretching alongside olive groves and golden wheat fields. This landscape shifts with the seasons, revealing stunning palettes of color from the fresh greens of spring to the sun-drenched ripeness of fall. De Gustibus Tours’ commitment to family-owned, organic, and biodynamic wineries ensures that guests connect with sustainable practices and authentic craftsmanship.
This experience offers a rare chance to step off popular routes and savor Tuscany’s quieter, more genuine rhythms. With personalized attention, wheelchair accommodations upon request, and options for food allergies, the tour is accessible and welcoming. Whether a wine aficionado or a curious traveler, this journey through Cortona and its valleys is a powerful reminder of Tuscany’s enduring allure beyond postcard vistas.
easy.
8 hours.
Suitable for most fitness levels; involves comfortable walking on uneven surfaces with frequent stops.
Yes, all ages are welcome; however, under-16s will be served non-alcoholic beverages in compliance with Italian law.
Absolutely. Please inform De Gustibus Tours at booking about any allergies or food preferences.
Yes, private transfer is included to and from your designated meeting point in Florence.
De Gustibus partners with family-owned vineyards emphasizing organic and biodynamic practices.
The tour includes light to moderate walking over uneven terrain, suitable for most fitness levels.
Yes, the tour operates throughout the year with slight adjustments to seasonal conditions.
Cortona, dating back over 2000 years, thrived during Etruscan and Renaissance periods, attracting cultural figures and wine enthusiasts alike.
The tour highlights sustainable vineyard practices that preserve soil quality and promote biodiversity in this region.
De Gustibus Tours is a Florence (Firenze, Toscana) based tour operator offering a range of private and curated experiences across Tuscany. The company presents a variety of itineraries that combine wine tasting, regional cuisine, historic towns and unique transport options such as vintage sidecar rides. Many published itineraries include private options and range from short city food rides to full-day wine and culinary tours. Published trip descriptions show itineraries to key Tuscan destinations including Chianti, San Gimignano, Montalcino, Montepulciano, Cortona and Val di Chiana. Signature experiences listed include sidecar aperitivo rides at sunset, street-food sidecar tours in Florence, Brunello and Vernaccia wine tastings, saffron- and pecorino-focused lunches, cooking classes in a Chianti farmhouse, and truffle hunting excursions. Several tours note visits to family-run wineries, organic farms for Tuscan lunches, and opportunities to sample local products such as Vino Nobile di Montepulciano, Vernaccia di San Gimignano, Brunello di Montalcino, Syrah from Cortona, pecorino cheese and saffron. Trip durations in published summaries vary from approximately two hours (street food rides) to five-hour sidecar excursions and seven- to eight-hour full-day tours. Departures are described as originating from Florence and cover regions such as Chianti Classico, Val d'Orcia and the hill towns surrounding the city. All information above reflects De Gustibus Tours’ published itineraries and trip summaries.
Book with De Gustibus Tours