Unforgettable Day Trip from Florence: Explore Cortona and Montepulciano with Guided Wine Tastings

Read the full experience

Just a short drive from Florence lies a journey through the heart of Tuscany’s rich history and world-renowned wine culture. This full-day excursion whisks you away to two of the region’s most captivating towns, Cortona and Montepulciano. Starting in Florence, you'll travel comfortably by van to Cortona, an ancient Etruscan hill town perched above the Valdichiana valley. Here, winding stone streets, medieval walls, and sunlit piazzas reveal stories from centuries past. A knowledgeable local guide leads you through Cortona’s historic center, bringing to life tales of its Etruscan origins and Renaissance splendor, with highlights including the Piazza della Repubblica and the impressive Palazzo Comunale. After soaking in Cortona’s timeless charm, the adventure continues towards Montepulciano, a town famed for its breathtaking views and robust wines. Nestled amidst the rolling Tuscan hills, Montepulciano offers a distinctive blend of splendid Renaissance architecture and viticultural excellence. At a historic winery, you’ll embark on a guided tour of the cellars, learning about the unique terroir and traditional production methods behind the celebrated Vino Nobile di Montepulciano. The tasting experience includes a variety of wines paired with a light Tuscan lunch, allowing you to savor local flavors alongside your glass. This tour crafts a seamless marriage of culture, history, and gourmet indulgence, perfect for travelers eager to dive beyond Florence’s city walls. The private van transport ensures relaxed travel between stops, while the expert guide enriches your understanding of Tuscany’s legacy. This trip stands out because it captures two distinct but complementary atmospheres: the ancient hillside village life of Cortona and the viticultural heritage of Montepulciano’s vineyards. Whether you're a history buff admiring medieval architecture or a wine enthusiast eager to explore Italy's iconic varietals, this tour offers an authentic slice of Tuscany. Cortona’s quiet charm combined with Montepulciano’s culinary and oenological richness creates a compelling travel experience hard to replicate elsewhere.

Trip highlights

Difficulty

easy.

Duration

8 hours.

Fitness level

Suitable for travelers in moderate physical shape comfortable with walking on uneven surfaces for a few hours.

Frequently asked questions

Is transportation included in the tour?

Yes, roundtrip van transportation from Florence is included for all guests.

Are the wine tastings suitable for beginners?

Absolutely, the guided tastings are designed to be enjoyable and educational for all levels.

Is lunch included during the tour?

Yes, you’ll enjoy a light Tuscan lunch paired with wine at the Montepulciano winery.

Can dietary restrictions be accommodated?

Please notify the tour operator in advance for any special dietary needs.

How much walking is involved?

There is moderate walking on uneven cobblestone streets, so comfortable shoes are recommended.

What time does the tour start and end?

The tour generally lasts about 8 hours, starting in the morning from Florence and returning in the afternoon.

Local insights

Wildlife

Common kestrels soaring over vineyards
Eurasian hoopoes spotted near olive groves

History

Cortona was one of the major Etruscan cities, later flourishing under Roman and medieval rule, enriching the area’s layered heritage.

Conservation

Many wineries here follow sustainable practices, preserving the landscape and promoting organic viticulture to protect Tuscany’s environment.

About Bologna Tour

Bologna Tour is a guided experiences provider based in Arezzo, Toscana, offering a wide selection of private and group tours across northern and central Italy. The company lists walking tours, boat tours, culinary tastings, museum and gallery visits, and full-day excursions that connect major cultural centers and smaller towns. Tour options include guided city walks in Bologna, Milan, Venice, Florence, Verona, Mantua, Vicenza, Parma and Siena; boat experiences on Lake Garda, Lake Como, the Venetian islands and Capri; motor and speedboat trips in Sirmione; and specialized itineraries to Ferrari and Lamborghini museums in Modena and Maranello. Bologna Tour’s catalog features food-focused experiences such as Taste Bologna food walks, Parmigiano and balsamic vinegar tastings, cooking classes, wine experiences in Chianti and Val d'Orcia, and regional farm visits. Cultural offerings include guided access to UNESCO sites, the Uffizi and Accademia small group visits, and archaeological excursions such as Pompeii and Matera. Transfers, private day trips from Bologna and port excursions are also provided. Bookings reference certified guides for certain city tours and include both private and small-group formats. Descriptions highlight meeting points, typical durations, and combined activities like aperitivo in Milan or boat-and-walking combinations in Sirmione. Travelers can choose experiences by city, theme or duration, matching urban exploration, food and wine, or automotive heritage visits throughout Italy. Listings include detailed summaries, meeting points, durations, and booking options for each trip, and many tours operate as private or small-group experiences across cities such as Bologna, Milan, Venice and Florence with flexible start times.

Base locationFirenze, Toscana

Tours offered199+

Specialty

Adventure tips

Book in advanceThis popular day trip fills up quickly, especially in spring and fall—reserve your spot early to ensure availability.

Wear comfortable shoesCobblestone streets and uneven surfaces in Cortona and Montepulciano require sturdy walking shoes.

Bring a light jacketEvenings can be cool, particularly outside summer months—layer up for comfort during winery tastings.

Stay hydratedCarry water while walking through towns and between venues, especially in warmer months.

Recommended gear

Comfortable walking shoes: Ideal for navigating historic streets and light hiking around vineyards.
Light jacket or layers: Provides comfort during cool autumn weather and indoor/outdoor transitions.
Reusable water bottle: Staying hydrated is key during your tour and wine tastings.
Camera or smartphone: Capture stunning hilltop townscapes and vineyard vistas.