

Tuscany and Umbria without the crowds
26 October - 2 November 2025
Embark on a soul-stirring journey through Tuscany and Umbria, where each day is a celebration of Italy’s culinary heritage, timeless landscapes, and warm-hearted traditions. From savouring legendary steak at a legendary butcher shop to cycling around Lake Trasimeno, cooking in a farmhouse kitchen, and foraging for truffles on a scenic Umbrian farm, every experience is rich with authenticity. Explore medieval Siena, sip Brunello in Montalcino, and soak in Florence’s Renaissance splendor—with plenty of time to linger in charming piazzas, toast with local wine, and enjoy the slower rhythm of Italian life. This is not just a trip—it’s a love letter to la dolce vita.
This trip is perfect for food enthusiasts, wine connoisseurs, history lovers, and adventure seekers who want to immerse themselves in the authentic experiences of Tuscany and Umbria. Whether you’re passionate about cooking, indulging in local wines, cycling through picturesque landscapes, or exploring centuries-old towns, this tour offers a blend of luxury, culture, and adventure. It’s ideal for those looking to explore Italy’s culinary heritage, charming villages, and rich history in a truly unforgettable way.
Highlights:
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five nights in a five star boutique hotel in the historic centre of Cortona
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two nights in a four star boutique hotel in the historic centre of Florence
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a day of cycling around Lake Trasimeno
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a hands-on cooking class in the countryside outside Siena
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truffle hunting and lunch in Umbria
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a winery visit and lunch
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time each day to do as you please
Sample day:
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8:00am: breakfast at our hotel
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9:00am: depart for a farmhouse in the countryside outside Siena for our hands-on cooking class and lunch
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2:30pm: arrive in Siena to explore at our leisure
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6pm: return to Cortona
This trip includes:
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Five nights shared (double) accommodation in a luxury boutique hotel in the historic center of Cortona
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All activities, tours and tastings outlined in the itinerary as well as private transportation to/from these activities
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Breakfast every day, three lunches and two dinners
The trip does not include:
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Flights
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Airport transfers
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Alcohol outside of included tastings
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Mandatory medical insurance
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Optional trip cancellation insurance
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Incidentals
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Gratuities
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Anything not outlined in “included” list
Something to consider:
We will spend a couple of hours each day in an air-conditioned vehicle, driving through the beautiful Tuscan countryside in order to reach the various wine-growing regions and travel between wineries. Tuscany is 68% hill! Expect to come across some steep climbs and cobblestone paths, but the views are worth it!
Trip cost:
$6300 Canadian dollars