On July 13, 2015, I joined a small-group walking tour with Walks of Italy through the heart of Tuscany. The itinerary promised a day of rolling hills, medieval hill towns, and local food — but what I hadn't expected was how perfectly it suited a solo traveler. No awkward silences, no forced group bonding. Just a dozen people who wanted to walk, taste, and listen, each at their own pace.
The meeting point was at a café near Florence's Santa Maria Novella station. Our guide, a woman named Elena who had grown up in a village outside Siena, carried a leather satchel stuffed with maps and a thermos of espresso. She didn't start with a lecture. She simply asked us what we wanted to see. One woman said "a vineyard where I can touch the grapes." Another said "a view that makes me stop talking." Elena smiled and said, "That's easy."
Walking Through the Landscape
We drove out of Florence in a minivan, windows open to the scent of hay and wild fennel. The first stop was a short walk from a farmhouse near Greve in Chianti. The path was narrow, lined with olive trees and wild rosemary. Elena pointed out a small stone chapel half-hidden by ivy and told us it had been a resting place for pilgrims since the 13th century. I walked at the back of the group, letting the sound of footsteps and birds replace conversation.
For solo travelers, this kind of guided walk is a quiet gift. You are never alone, but you are never required to perform. You can ask a question or simply observe. The group itself becomes a gentle container — you share a table at lunch, you pass the water bottle, you help someone take a photo. But the experience remains yours.
Monteriggioni: A Town That Refuses to Rush
By late morning we reached Monteriggioni, a walled village that has changed little since Dante wrote about it. The main street is a single cobbled lane. Elena led us to a tiny courtyard where a woman named Lucia was making pici pasta by hand. We watched her roll the dough into thick, uneven strands, then ate them with a sauce of garlic, tomato, and pecorino. There was no menu, no prices. Lucia simply brought out bowls and told us to eat.
That meal taught me something about slow travel that I still carry. The best experiences are not curated. They happen because someone trusts you to be present. Lucia didn't check our IDs or ask where we were from. She just handed me a bowl and said, "You look hungry." I was.
Wine and the Art of Not Doing
After lunch we visited a small winery on a hillside near Castellina in Chianti. The owner, a man in his seventies named Paolo, walked us through his cellar — a cool, dark space where the barrels were stacked three high. He spoke in Italian, and Elena translated only when he paused to laugh. Paolo didn't explain the wine. He poured it. Then he poured it again.
I sat on a stone wall outside, glass in hand, watching the light change over the valley. A woman from the group joined me and said, "I've been trying to take a picture of this view for ten minutes. It doesn't work." She was right. Some things resist being captured. That's the point.
Wine tasting in Tuscany can feel performative — swirling, sniffing, using the right adjectives. But Paolo's approach was the opposite. He handed me a glass of Chianti Classico and said, "Drink it now. Or later. I don't care." That freedom, the permission to simply be, is what makes solo travel so transformative. As I wrote in a previous post about 8 Films That Will Make You Want to Travel Solo (Reader Favorites), the best journeys are the ones where the script is unwritten. This day was exactly that.
Practical Details for the Solo Traveler
- Tour size: Walks of Italy keeps groups small — ours was 12 people. This makes it easy to chat without feeling crowded, and you never lose the guide in a crowd.
- Pacing: The walking is moderate. You cover about 5 kilometers total, with plenty of stops. Wear comfortable shoes, but leave the hiking boots at home — the paths are well-trodden.
- Food: Lunch is included and generous. If you have dietary restrictions, let the company know in advance. Lucia's pasta was vegetarian-friendly, but the cheese course may not be.
- Solo-friendly: The tour is designed for individuals, not just couples. I saw several solo women in the group, and the guide made a point of checking in with each person without being intrusive.
San Gimignano and the Art of Leaving
Our final stop was San Gimignano, famous for its surviving towers. Elena gave us an hour to explore on our own. I climbed one of the towers — a narrow, steep staircase of 200 steps — and at the top, the view opened across the entire Val di Elsa. I could see the road we had driven, the vineyard where Paolo had poured wine, and far in the distance, the dome of Florence's cathedral.
Standing there, I felt the particular loneliness that solo travelers know: not sadness, but a kind of clarity. I was the only person seeing this exact moment. No one would ask about it later. The memory belonged entirely to me. That is the trade-off of traveling alone — you lose the shared story, but you gain a private one.
On the drive back to Florence, the group was quiet. Someone fell asleep. Someone was reading a guidebook. I was thinking about how a single day can feel like a week when it's filled with the right kind of attention. Just as a Perfect Day in Split: A Local's Itinerary showed me that a well-planned day can unlock a city, this Tuscan walk unlocked an entire region.
What I Would Do Differently
If I could redo that day, I would bring a small notebook. Not for notes on the tour, but for the names of the people I met — Lucia, Paolo, the woman from the group who shared her water. I would also skip the espresso at the meeting point and save my caffeine for the afternoon, when the wine started to make me sleepy. And I would wear a hat. The July sun in Tuscany is generous, but it does not negotiate.
The tour ended at 6:30 PM back at Santa Maria Novella. I walked to a nearby trattoria and ordered a plate of ribollita, the Tuscan bread soup, alone. The waiter asked if I was on a tour. I said yes. He said, "You look like you found what you were looking for." I smiled and said, "I think so."
