550€ per Person | 8 hours | Discover Cortona and Montepulicano
Take a private tour from Florence to the historic hilltowns of Cortona and Montepulciano. Explore Etruscan history before indulging in castle winery tours and classic Tuscan wine tastings.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for travelers in moderate physical shape comfortable with walking on uneven surfaces for a few hours.
Wildlife
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.
Bologna Tour
550€ per Person | 8 hours | Discover Cortona and Montepulicano
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 Location
Arezzo, Toscana
Tuscan headquarters
Private & Group
Private & Group Tours
Options for couples to groups
Destinations Covered
Italy-wide
From Milan to Sicily
Tour Types
Walking, Boat, Wine
Cultural, food & day trips
Find private or group experiences from Arezzo, Toscana to Milan, Venice and beyond — check availability and book clear itineraries online.
Book in advance
This popular day trip fills up quickly, especially in spring and fall—reserve your spot early to ensure availability.
Wear comfortable shoes
Cobblestone streets and uneven surfaces in Cortona and Montepulciano require sturdy walking shoes.
Bring a light jacket
Evenings can be cool, particularly outside summer months—layer up for comfort during winery tastings.
Stay hydrated
Carry water while walking through towns and between venues, especially in warmer months.
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.
fall
Reusable water bottle
Staying hydrated is key during your tour and wine tastings.
summer
Camera or smartphone
Capture stunning hilltop townscapes and vineyard vistas.