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ITALY
La Dolce Vita, Uncrowded
From olive oil mills to castle estates, discover the flavours, textures and warmth of Tuscany’s off-season—crafted with intention by Victory Travel & Events, specialists in bespoke small-group touring.
By Madelaine Laframboise
Tuscany in mid-fall feels like a long, slow exhale. The summer heat softens, crowds thin, and the region reveals a quieter side. There’s no rushing only savouring the tastes alongside the noble terroir.
Travelling with Victory Travel & Events, a bespoke small-group company with more than 20 years of experience crafting intimate journeys, I join 15 to 20 guests. Our group is small enough for deep connections, yet large enough to share discoveries. With our guide orchestrating every detail for this adults-only culinary tour, all I needed to bring was curiosity and an appetite for slow travel.
Settling into Siena
The tour starts in Rome, but Tuscany truly takes shape in Siena, where medieval walls glow warmly under autumn light. Our base, Villa Scacciapensieri, sits just outside the historic centre, surrounded by fragrant gardens clinging to their last roses. Victory Travel & Events’ philosophy—fewer hotel changes, more immersion—sets the tone of relaxed elegance. I drop my bags, and ease into a slower Tuscany.
Our welcome dinner unfolds at the villa. Wood-fired pizza, local wine and a soft jazz trio ease us into Tuscan evenings. No chain hotels here.
The next morning, I step into the sunlit kitchen of Fonte Giusta Academy. A local chef presses dough into my palms, guiding me through kneading, folding, and shaping. The repetitive motions are meditative, and by the time we taste our pasta, the act of cooking grounds me in this moment.
Vineyards, Olive Mills, and Tuscan Flavours
We travel deeper into the southern Chianti region and the “Slow City” of Castelnuovo Berardenga. At Cantina Vallepicciola, Tuscany literally appears in a glass. Cypress-lined vineyards frame a tasting of Chianti reds, their notes of berries and forest echoing the autumn landscape. The winemaker lingers with us, sharing stories as rich as the wine.
Leaving Siena, our private bus follows winding ridgelines to Abbazia Monte Oliveto Maggiore, a Benedictine monastery tucked into the countryside. Cool cloisters offer a moment of stillness before we sample the monks’ wines, each sip a reminder of craft and history. Later, at a local olive mill, bright green olio nuovo drips onto warm bruschetta, its bite a delicious hallmark of the harvest.
San Gimignano greets us with towers rising into a crisp blue sky. Nearby, Pienza, a Renaissance gem glows in soft fall light. In both towns, Victory Travel & Events builds in generous free time—no guided tours, no rush—just space to linger and enjoy the ambiance.
Castles, Cellars, and Florence’s Quiet Splendour
In Montalcino, the landscape shifts to wilder valleys. Here, Castello Banfi, a MICHELIN Key-rated castle-on-a-hill, welcomes us with its vaulted cellars. Dinner is intimate: pillowy ravioli, braised beef cheeks, and rustic apple pie. Each dish is paired with Banfi wines that glow ruby by candlelight.
For more wine pleasure, we raise even more glasses at Antinori Winery. Considered Italy’s top wine producer, the modern winery pairs its jaw-dropping, earth-sculpted architecture with voluptuous, berry-rich pours.
Our final day unfolds in Florence, the birthplace of the Renaissance. Our hotel, Croce Di Malta, has a rooftop bar that is so close it feels like you can touch the Duomo. In the afternoon, I stand inside the Duomo, climb Giotto’s bell tower, and wander the Baptistery of San Giovanni, without the crush of summer tourists. And with Victory Travel & Events, in this quiet season, la dolce vita unfolds at exactly the speed it’s meant to.
2026 Tuscany Wine and Food Tour | October 1-10, 2026
Experience Tuscany on a small-group journey curated by Victory Travel & Events. With a maximum of 30 guests, this 9-day itinerary blends culinary discovery, culture, and unhurried immersion in some of Tuscany’s most storied landscapes. Inclusions: accommodations, ground transportation, transfers, excursions and city tours, four winery tours, and most meals and drinks. Rates are from $5,000 CAD. Airfare is additional.
Travel Planner
For booking information about the 2026 Tuscany Wine and Food Tour, visit www.VictoryTravel.ca or email info@victorytravel.ca
