Places: Siena, Pisa, San Gimignano, Montepulciano, Pienza, Colle di Val d’Elsa, Chianti Region, Val d’Orcia, Maremma, Livorno, Montalcino, Arezzo, Cortona, Saturnia hot springs
Tuscany isn’t just a region, it’s a vibe. Rolling hills, cypress-lined roads, medieval villages, and world-class wines make it a darling for every kind of traveler. Everyone can make the most of it, no matter what they are seeking!
Chianti Valley
For those who love picture perfect towns there is Siena, Piazza del Campo and it’s wonderful seasonal markets! God knows I have shopped everything from food to clothes, to leather bags from here! The towers of San Gimignano are UNESCO listed, but some of my best memories come from its gelato.
Right in the city center, two globally acclaimed gelaterias face each other. Obviously we tried both and were blown away by how different and distinct the gelatos were! Walking through this small medieval town, we also stumbled upon a quirky artifact shop unlike anything I’ve ever seen: it’s a treasure trove of props and memorabilia from all superhero and fiction movies you can image! That shop is a piece of art!
A stop at Pienza makes sense to taste their world famous pecorino cheese, and at Arezzo and Cortona , for the frescoed churches, artisan shops, and sweeping hilltop views for nature lovers and amazing vintage shopping for those who are like me! 🙂
San Gimignano
And now the crowning jewels of the region, Val d’Orcia a forever favorite movie location, and Montepulciano & Montalcino! Did you know that these two regions produce two unique wines Vino Nobile and Brunello that is not found anywhere else in the world?
One of our fondest memories of this region is driving through the valley during sunset, and going wine tasting in a boutique vineyard! The vineyard, run entirely by women, owned by two sisters, arranges these curated wine tasting experience in their property, overlooking the valley and produces only 5000 bottles of wine every year, that is delivered to only special guests and partners!
Val D Orcia
I cannot end without mentioning Saturnia hot spring, the cascading turquoise pools, fed by warm sulfur-rich waters that stay around 37°C year-round. And the more elusive Bagni San Filippo, tucked inside a forest, making it a favorite of localites and photographers!
No matter what draws you to Tuscany, whether it’s sipping wine on a hilltop, exploring ancient streets, chasing the perfect pasta, or lounging on a hidden beach, this region delivers.
The key to best enjoy Tuscany is to plan your route around the season, choosing destinations that match your travel mood, designing your road trip for the best experiences, and knowing how to reach those secluded gems!
An Afternoon at a Tuscan vineyard in Montepulciano
Author – Adrita
The crown jewel of the Tuscan region (no points for guessing) is its world class wines. Yet so many tastings today feel rushed and clinical, an item to check off rather than an experience to truly relish!
I wanted something different, something warm, personal, and rooted in the stories of the people. We started with our research and soon enough stumbled upon just this incredible place!
Perched on a medieval hilltop town of Montepulciano, this vineyard sits at the end of a long beautiful path lined with tall Tuscan cypresses. As you drive into the walkway, the view opens onto a rolling vineyard stretching as far as the eye goes. To the left stands a charming old chateau, with a glass and stone patio. The chateau houses around 12 rooms for guests who want to enjoy a vineyard retreat.
As soon as we stepped out of the car, we realized the air was a heady blend of fruits, flowers and earth. Waiting to greet us was a group of women, gracious and smiling!
This vineyard, a vintage family estate now run by two sisters, is tended entirely by women, from the rows of grapes to the heart of the cellar. We began with a tranquil walk through the vines, learning about the ‘grape sleeping season’ before wandering into their compact but fascinating production area. Massive steel vats brimmed with grape slurry in varying stages of becoming wine, powered entirely by women. We learned that this vineyard produces only 5,000 bottles a year, shared exclusively with a select circle of partners and clients and they plan to keep it that way.
After the tour, we settled into the patio for our wine tasting. The chef emerged with their charcuterie board of cheeses, fresh fruits, jams, crackers, and cured meats. We took our seats around an antique chestnut table, its centerpiece adorned with pinecones, candles, and dried blooms. One stone wall had been converted into a wine chest showcasing bottles aged up to 18 years.
Family owned wine estate
We had just settled down when one of the sisters holding a bottle of deep red, began to pour. As the ruby liquid shimmered in our glasses, she shared charming anecdotes about being women in the wine industry. One pour led to another, and laughter and stories flowed as easily as the wine.
It felt less like a tasting and more like an afternoon among friends, sharing tales about our lives away from India, our love of travel, and the more inexplicable things that connect people across the globe! We asked about staying a night at their beautiful vineyard retreat, only to be told it’s booked months in advance (no surprise there)
When it was finally time to leave, a couple traveling from the Caribbean arrived and joined us for one last toast. As we waved goodbye, we knew we’d be back, not just for the wine, but for the warmth and women who made that afternoon unforgettable!
Enroute wine tasting in this age old castle vineyard
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