Unforgettable Day Trip from Florence: Explore Cortona and Montepulciano with Guided Wine Tastings
Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for travelers in moderate physical shape comfortable with walking on uneven surfaces for a few hours.
Overview
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.
From Florence: A Day in Cortona and Montepulciano with Wine Tasting
550€ per Person | 8 hours | Discover Cortona and Montepulicano
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Adventure Photos
About This Adventure
Embark on a private tour from Florence to the enchanting towns of Cortona and Montepulciano. Explore Cortona's historic center with a knowledgeable guide, then indulge in a guided winery tour in Montepulciano, complete with exquisite wine tastings and a light lunch. Experience the perfect blend of history and fine wine in Tuscany.
Embark on a private tour from Florence to the enchanting towns of Cortona and Montepulciano. Explore Cortona's historic center with a knowledgeable guide, then indulge in a guided winery tour in Montepulciano, complete with exquisite wine tastings and a light lunch. Experience the perfect blend of history and fine wine in Tuscany.
Adventure Tips
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.
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.
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Adventure Hotspots in Florence
Frequently Asked Questions
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.
fall specific
Reusable water bottle
Staying hydrated is key during your tour and wine tastings.
summer specific
Camera or smartphone
Capture stunning hilltop townscapes and vineyard vistas.