Tuscany is known for its food and wine—and for good reason. We spent time doing both, and it absolutely lived up to expectations. But what stood out just as much was everything outside of the tastings.

Some of the best moments came when we stepped away from the table and into the countryside.

A Closer Look at Tuscany’s Wine Experience

We visited two wineries during our time in Tuscany, and each one came together in a different way.

San Donato (Chianti Region)

Our visit to San Donato wasn’t a formal tasting; instead, it turned into something much more personal and very casual.

We had emailed ahead to let them know we planned to stop by as recommended by Macs Adventure, but we didn’t have a reservation. When we arrived, we didn’t immediately introduce ourselves. A woman in the office just off the wine shop told us to have a seat in the courtyard and said she would bring us some wine.

It turned out she was the owner’s wife, Federica.

What followed felt less like a structured tasting and more like being welcomed as a Pilgrim passing through. She brought out wine, sat with us, and shared stories about the winery and her family. We ended up interviewing her—something you’ll hear on an upcoming episode of the Sunshine Travelers Podcast.

Before we left, she had the kitchen prepare sandwiches for us to take with us. 

Alteeza (San Gimignano Area)

We visited Alteeza the next day near San Gimignano, and this one wasn’t planned.

We had set out on a loop walk around town and came across the winery early on. We decided to stop in.

That’s where we met Gabriele, the sommelier. He shared that the winery had been in his family for generations, and once he learned we had a podcast, the experience became more in-depth. He walked us through the wines, explained the region, and spent time answering questions in a way that you don’t always get in a typical tasting.  And he was thirsty, so we needed to try more wine.

We’re hoping to bring that experience full circle and have Gabriele join us for a wine tasting at our home in the future.

It’s easy to focus on the wineries and the towns, because for most people that is what they plan their trips around.

But the part of Tuscany that stays with you is what sits between them.

Why the Countryside Matters Just as Much

It doesn’t take much to get beyond the main squares and into open landscape.

Just outside towns like Volterra, San Gimignano, and Siena, you’ll find:

• Vineyards stretching across the hills

• Olive trees that have been producing for generations

• Gravel paths with very little traffic

• Quiet surroundings where you mostly hear birds and wind

This is where everything connects. The towns, the farms, and the wineries all sit within the same landscape—you’re just moving through it.

Walking the Via Francigena: Strove to Monteriggioni

Another highlight was walking from Strove to Monteriggioni, part of the historic Via Francigena.

This route dates back to the Middle Ages and connected Canterbury to Rome, with some travelers continuing on toward Jerusalem.

These journeys often took months or longer.

Along the route:

• Towns developed to support travelers

• Inns and churches were built along the way

• Communities formed around people passing through

The section into Monteriggioni stands out because of the setting. You walk through open countryside and then approach a fully walled medieval town that still looks much as it did centuries ago.

The towers along the city walls are arranged in a way that resembles a king’s crown, which is where the town’s name is said to come from. Seeing it from a distance as you approach makes that connection easy to understand.

The trail is well-marked and easy to follow. You don’t need to walk the entire route to appreciate it—just experiencing a portion gives you a sense of its history.

Bringing It All Together

Tuscany delivers on food and wine, but the experience becomes more complete when you combine that with time outside.

You can spend part of your day at a winery and another part exploring the countryside. They don’t have to happen back-to-back, and for many people, it’s better if they don’t.

What matters is giving yourself enough time to do both.

You can plan a winery visit one day and head out on a walk the next. Or build in a lighter afternoon after a tasting and get out into the hills. However you approach it, the combination is what makes Tuscany stand out.

You taste the wine, then see the landscape it comes from.

You visit a town, then walk the paths that connect it to others.

That’s where the experience comes together.

Planning Your Own Tuscany Experience

If you’re thinking about visiting Tuscany and want help building an experience that goes beyond the typical stops, we’d love to help.

At Sunshine Travelers Experiences, we design trips that combine food, wine, and experiences like this—ones that don’t always show up in a standard itinerary.

And keep an eye out for our upcoming podcast episode, where we’ll share more from both of these winery visits.