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Travel Story: On Foot Through Picturesque Tuscany

Lilly shares her story of exquisite cuisine and places to fall in love with
Woman hiking through green vineyard rows in Tuscany with cypress-lined hills and historic buildings visible in the background under blue sky.

New year, new journey—but this time, I wanted to try something different. Over the past two years, I’ve explored Italy by bike, sharing my experiences from Bolzano to Venice and from Pisa to Florence. Italy is, without a doubt, one of my favorite destinations in Europe.

This year, however, I’m leaving the bike at home. Instead, I’m packing my hiking boots and my dear friend, Robert. We are both so excited to experience the picturesque Tuscan landscape up close and on foot. Robert and I have one big thing in common: we love great food and are "active foodies" through and through. Between the stress of home renovations and the daily grind of a construction site, this was going to be the special getaway we’d been looking forward to for months. 

Our journey takes us from one stunning city to the next, straight through the lush greenery of Tuscan wine country, all the way to the Tyrrhenian Sea.

Woman hiking through green vineyard rows in Tuscany with cypress-lined hills and historic buildings visible in the background under blue sky.

Arriving in My Beloved City: Florence

The city of art, the cradle of the Renaissance, and the heart of Tuscany. To spend time here is to breathe pure history while soaking in the vibrant life between magnificent palaces and golden sunsets over the Arno. We knew beforehand that we had to plan a few extra days both before and after, to truly dive into the dolce vita and explore my favorite city. I love jogging across the Ponte Vecchio in the early morning, just as the city begins to wake and the light bathes the river in warm, golden tones.

Then, it’s time for a cappuccino at a small café to people-watch and simply settle in. Between visiting the imposing Santa Maria del Fiore Cathedral and shopping in the Santo Spirito district, a stop at one of the famous wine holes—the buchette del vino—is a must. You ring the bell, and an arm reaches out of a tiny window with a glass of red wine; it’s the kind of experience you can only find in Florence.

Greve in Chianti: A Tuscan Picture-Book Setting

On Sunday morning, after our hotel briefing, we made our way to the bus stop. We boarded the bus to Il Ferrone in pouring rain—not exactly an ideal start! But it quickly led to our first friendly encounters with fellow travelers embarking on their own Eurohike adventure through Tuscany. A quick glance at the weather forecast lifted our spirits: after the 45-minute ride, the sun was expected to chase away the downpour.

And sure enough, it did. Following the Eurohike on Tour app through airy stretches of woodland, Tuscany suddenly revealed itself in all its classic, dreamlike glory—vineyards, ancient stone houses, and towering cypress-lined avenues. We arrived in the charming town of Greve in Chianti and treated ourselves to a light afternoon snack before checking into our stunning hotel, Pietra del Cabreo.

MY TIP:

For this night, we opted for an upgrade to a ‘Charm’ hotel—for an extra fee—and it was absolutely worth it. Along with a beautiful suite and a pool overlooking the picturesque vineyards, we savored an exquisite dinner at the on-site CABREO Ristorante. Dining here is truly top-tier. If you enjoy a luxurious, indulgent evening to unwind, be sure to explore our Hike and Charm category.


 

Woman hiking through green vineyard rows in Tuscany near Castello Vicchiomaggio, with rolling hills and mountains under blue sky.

Wine Culture Heritage: Castellina in Chianti

Bathed in brilliant sunshine and fueled by a delicious breakfast, the first highlight of today’s hike awaited us right from the start: the small, quiet, and authentically Italian village of Montefioralle. At 9:00 AM, the village and its residents were still fast asleep, but we couldn’t resist quietly wandering through the narrow streets and along the medieval stone-paved lanes.

Our route then led us through woodland and past the rolling Chianti vineyards, with sweeping views over the vibrant green countryside. For early October, this isn’t something you can take for granted—but the rainy weeks beforehand had created a lush, late-autumn landscape.

By midday, we arrived in Panzano, a small town with a rich history. In the 12th and 13th centuries, it served as an important defensive and trading post for the already-famous Chianti wine. For us, it was time for a light lunch on the panoramic terrace of Bar Strafico.

We continued to Lucarelli, where we caught the bus to Castellina. At our destination, we redeemed our included voucher for a wine tasting at Ristorante Il Cantuccio and looked forward to a well-earned wood-fired pizza.

Two hikers with backpacks walking through green vineyard rows in Panzano, Tuscany. Rolling hills and olive trees frame the sunny landscape.

Siena: The City of the Palio and Medieval Streets

We set off early in the morning, stopping by the local panetteria to pick up some snacks for the road. From there, the path takes us downhill along gravel roads, past Tuscan villas and numerous agriturismi. The landscape here changes noticeably, shifting from the deep green of the vineyards to the earthy brown of the tilled fields.

We enjoy the peace of the Via Romea and the great conversations with every step as we hike toward the eternal city of Siena. In Quercegrossa, all the Eurohike guests gather; as it turns out, hiking into a major city sounds much more romantic than it actually is. Instead, we hop on the bus to save our energy for an extensive walking tour of the city itself.

Piazza del Campo in Siena with the medieval Palazzo Pubblico and its tall Torre del Mangia tower under a clear blue sky. People gather on the square.

The Famous 5 Towers of San Gimignano

Leaving the small villages behind, we started our hike toward San Gimignano, full of anticipation for this iconic city and symbol of Tuscan history. After a bus ride into the sleepy Val d’Elsa, we climbed the steep cobblestone streets from the lower square up into the old town. Early in the morning, the streets were empty; the silence and the crisp morning air were a true delight and left us with so many wonderful impressions. Once we left the town, we hiked mostly on paved roads and small meadow paths. Admittedly, this stretch isn't particularly spectacular, but it was made all the more enjoyable by the company of so many wonderful Eurohike guests. We spent most of this stage walking together, deep in conversation, including a lovely stop at a hidden "pilgrim café" tucked away in the woods.

A portion of today's route even follows the famous Via Francigena, a historic pilgrimage and trade route—though in our case, we weren't heading toward Rome with the rest of the pilgrims, but rather in the opposite direction. From afar, we caught our first glimpse of the town's famous and exceptionally well-preserved medieval towers. These "tower houses" once reflected the wealth and power of rival families and still give the city its unique, iconic skyline today. Since the day with our new hiking friends had been so pleasant, we decided—after a short rest at the hotel—to head out together to taste "the best gelato in the world" and round off the evening with a magnificent meal and excellent red wine.

Volterra: In the Footsteps of Etruscans and Alabaster

Today’s stage begins with a Eurohike-arranged bus ride into the Monte Nero Nature Reserve. Upon arrival, we hiked along an adventurous forest trail to a brief, but manageable, exposed section near a waterfall. While the tour description noted a "rushing waterfall," it turned out to be more of a small trickle in the autumn. For anyone feeling unsure about this specific passage, there is an alternative to stay on the bus for a few more stops.The final stretch along the Via del Sale (the ancient Salt Road) led us past accessible Etruscan burial chambers and the excavations of the Roman Amphitheater before reaching the city gates of the "Alabaster City," Volterra.

After a refreshing shower, we wandered through the narrow alleys until I stumbled upon a tiny, inconspicuous alabaster workshop. I’m so glad I followed my curiosity, or we surely would have missed this highlight! The elderly artisan showed us his works of art, and after I purchased one of his masterpieces, he even let me watch as he carved a small alabaster heart just for me as a thank-you.

Historic hilltop town of Volterra in Tuscany at sunset, showing terracotta rooftops, stone buildings, a dome, and a tall bell tower.

Sea in Sight: Reaching Cecina di Marina

On a clear day, you can spot the shimmering blue of the horizon right from Volterra. From there, we took the bus to the terminal in Cecina and continued on to the Marina district. A peaceful stroll along the shores of the Tyrrhenian Sea followed, until we could see the dense pine forests appearing in the distance. The sun was shining, and even for early autumn, it was significantly warmer than expected—which made us appreciate the soothing shade of the trees even more as we walked barefoot over the soft carpet of pine needles.

Since the town is nearly deserted in early October, we had the sandy beach all to ourselves. We spent time looking at the heavy pieces of driftwood that serve as a natural building kit for visitors of all ages; this stretch of beach is dotted with everything from simple structures to impressive works of art created by both nature and human hands. To top off our seven-day hiking adventure, a dip in the refreshing water was an absolute must. It was the perfect conclusion to an unforgettable journey.

Olive tree in foreground with rows of vineyards in Greve in Chianti, Tuscany. Rolling hills and blue sky with clouds in background.

My conclusion:

A journey that will stay with you for a long time to come. If you want to combine enjoyment and culture with an active break, this tour is just right for you. Even if not every stage features high mountains and impressive coastal views, you can really switch off and do something good for yourself here. The reward awaits you after every stage of the hike.

My Favorite Active Moments Along the Way

While traveling along the most beautiful hiking trails in Tuscany, it is no easy task to pick just one favorite place. Often, it’s the many small moments along the way that truly make a journey special. As a culture lover, the unique flair of these Mediterranean cities was an absolute highlight of the tour for me. After a long day of hiking filled with great conversation, we stood together with our fellow travelers in awe of the famous towers of San Gimignano—a city that truly lives up to its history. 

Looking for even more inspiration from my hiking adventure through Picturesque Tuscany? Then sit back and join me for the most beautiful moments of the journey on our Eurohike YouTube channel

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