Determined to rediscover slow travel, Alicia Erickson explores the Tuscany wine region of Chianti on two feet
On a late August morning, I wake up to the sun streaming through an arched stone window overlooking the tiny commune of Gaiole, Tuscany. Despite the plush bed inviting me to linger, I have a mission ahead of me. Over the next several days, I am walking through the pine forests and vineyards of Sienese Chianti.
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Donning a backpack filled with water, snacks and a charged phone and camera, I lace up my hiking shoes and I’m on my way. I bypass holidaygoers enjoying breakfast on the terrace and continue down into the cobblestone streets of the quaint Tuscan town painted in earthen shades of yellow, blue, orange and peach, where the early birds sip coffee at street side cafes.
The self-guided sojourn has been organised by Macs Adventures, a travel company specialising in multi-day hiking and cycling holidays in Europe and the UK. The idea is simple: ditch the vehicle and embrace the beauty of slow travel. Luggage is transported between accommodations, and the guests follow daily routes easily accessible on digital maps. My chosen route takes me through the historic towns and rolling hills of Chianti, giving me a taste of the region’s culinary finesse, wine heritage and bucolic scenery.
On my first day, feeling fresh and eager to hit the road, I take in each detail of the scenery. I walk down the steep hill into Gaiole, passing the iconic black rooster — a legendary symbol of the Chianti region of Tuscany — and briefly admire the stone cathedral. The map for today’s route directs me along a gentle path out of town. Before long, a light rain begins to fall — a welcome reprieve from the intense heat that had fallen upon much of Italy the previous weeks.
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Along the way, I pass petite, family-owned vineyards, olive oil farms and artisanal farm shops. I walk through quiet woods over a carpet of pine needles and through the unassuming hamlet of Montegrossi. Before long, the sun is shining again.
After several miles, I follow a long and winding hill to reach Badia a Coltibuono, a 12th-century monastery with hallowed halls and exquisite views over the valley below. The monastery is now home to a culinary school and café set among rose gardens. I dig into a plate of summer vegetable gnocchi and sip a glass of Vermentino — a perfect reprieve before continuing back along the winding roads to Gaiole.
There’s time to slip into Castello di Spaltenna’s sprawling infinity pool before my wine-paired tasting menu at II Pievano, Spaltenna’s Michelin-starred restaurant, where the focus is on seasonal, playful menus. Sitting beneath the stars surrounded by open castle walls, dusting off the final dessert course, I relish the many joys of slow travel.
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The next morning, I bid farewell to Spaltenna and set off, down ravines, across open fields and among ripe, leafy grape vines on the cusp of harvest season. The hills are airbrushed with orange gold, hinting at the first signs of autumn. With the sun shining brightly, I optimistically remove my raincoat. Moments later, the skies open again, but I forge on, my eyes set upon a castle atop a hill faintly visible through a sheet of rain.
By late morning, I stumble into the grand fortress of Castello di Meleto dripping wet. After a half-hearted attempt to dry off in the bathroom, I sit down for a wine tasting in a thousand-year-old castle that specialises in the production of Chianti Classico. I sample four Chianti wines, each made from Sangiovese grapes grown on different sites, and each crafted with a nod to the terroir.
Warmed from the inside out thanks to the generously poured vino, I continue towards my final destination for the day: Hotel Le Fontanelle, a restored 13th-century mansion. Pine forests and winelands blur together as my feet squish in wet socks and shoes. Growing tired of this drenched day, I check my map: still almost 10 kilometres to go.
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The damp forests eventually open up to olive farms and rustic farmhouses. I spot a welcome sight: the elegant La Fontanelle perched atop exquisite Tuscan land. With muddy, sopping shoes and a sweaty backpack, I walk through the elegant courtyard, much in need of a shower and siesta.
The next day, I take a break away from maps and hiking, and instead head to the family-run Riecine winery, where a modest tasting room overlooks deep green vineyards against the backdrop of the pine forest. Inside, wine ages in egg-shaped concrete vats, and bottles from each of the winery’s vintages, dating back decades, line the walls. We taste our way through many iterations of Chianti Classico and Rosso Tuscano. Our wine guide graciously humours my curiosity, bringing out bottles of skin contact, among other speciality vintages to try.
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In a happy daze after sampling my favourite wine in the region yet, I while the afternoon away in La Fontanelle’s picturesque pool, the sun glimmering on my face until a crack of thunder and a rainstorm opens over the rolling hills. I retreat to the cosy sitting room for an aperitivo before a dinner of spaghetti topped with shaved truffle.
On the final day of my Tuscan walking adventure, I’m bound for Siena, a medieval city that has often existed in the shadow of Florence. I savour the quiet of the countryside and the simplicity of walking through majestic green forests, bypassing regal wine estates and historic fortresses, including the Basilica dell’Osservanza, a 15th-century church.
Roads widen and cars zip by, the serenity of the countryside slowly fading. Naturally, my dreadful sense of direction kicks in, and I lose the correct path as I attempt to cross an overpass into the city. After a brief altercation with the digital map, I find my way through a steep arched entry where Siena greets me with fervour.
After refreshing in the stylish Grand Continental, I hit the city and walk to nowhere in particular, passing through narrow streets with tall stone and ochre buildings, admiring the Duomo — a soaring gothic cathedral — and eye high fashion boutiques from afar. I eventually stop at Pizzicheria de Miccoli, a cheese and charcuterie shop my Italian friend insisted was a must, where I savour a perfect spread of olives and cheese on a street-side wine barrel. I wander on to the Piazza del Campo and take a seat on the steps, the square abuzz with late summer vibes.
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To top off the evening, I grab a table in an atmospheric alley restaurant and order a plate of pici, Siena’s famed rustic pasta. Music and friendly chatter echo in the medieval corridors, as I linger, not wanting to bid farewell to Chianti just yet. But tomorrow, a walk through the farmlands of Umbria awaits.
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