This article was adapted from the original video published through her You Tube channel @texastomilandiyitaly

Weekend Trip To Tuscany

Looking back on my adventures, one of the most unforgettable weekends was my trip to Tuscany, where I explored Italy’s largest antique market in Arezzo, wandered the medieval streets of Orvieto, and stayed in a real-life castle—Castello di Valenzano. It was an early wedding anniversary getaway filled with history, incredible vintage finds, and stunning landscapes.

First Stop: Exploring Orvieto’s Historic Charm

Our weekend adventure kicked off in Orvieto, a striking hilltop town in Umbria. Built on a volcanic bluff, the city looks like something out of a storybook, with its medieval streets, dramatic cliffs, and fascinating underground tunnels.

We battled strong winds as we wandered through Orvieto’s charming alleys, but nothing could distract from the beauty of the place. The Duomo di Orvieto, with its golden mosaics and Gothic spires, was absolutely breathtaking. We also visited the 12th-century Church of Sant’Andrea, a hidden gem with stunning Romanesque architecture. Of course, a trip to Orvieto isn’t complete without trying its famous white wine—Est! Est!! Est!!! The legend behind the name? A German bishop’s servant was so impressed with the local wine that he marked “Est! Est!! Est!!!” (Latin for “It is! It is! It is!”) on the doors of the inns serving it. Naturally, I had to grab a bottle for myself.

Our Fairytale Stay at Castello di Valenzano

That night, we checked into Castello di Valenzano, a magical Tuscan castle nestled in the hills. Stepping inside felt like traveling back in time—stone walls, towering turrets, and grand halls filled with antiques. The castle’s misty, moody surroundings made it feel like a scene straight out of a medieval fantasy novel.

Each room had its own unique history, and I couldn’t help but imagine the nobles, warriors, and maybe even ghosts who once lived there. Waking up in a castle? Absolute dream.

Arezzo’s Largest Vintage Treasure Hunt

The next morning, I set off for Arezzo’s famous antique market—held on the first Sunday of every month (and the Saturday before). This is one of Italy’s largest and most prestigious antique fairs, drawing collectors and vintage lovers from all over the world.

The market sprawls across Arezzo’s historic center, winding through cobbled streets and picturesque piazzas. Every corner revealed something new—antique furniture, rare books, vintage jewelry, ceramics, and art. It was wonderfully overwhelming, and I had to resist the urge to buy everything in sight.

Some of my favorite finds:

• A vintage nativity set (presepe) – In pristine condition and so beautifully detailed.
• Intricate tasseled curtain tiebacks – Something I had been searching for forever!
• A set of ceramic ship coasters – A sneaky purchase that I initially resisted but now absolutely love.
• A tiny wind-up boat – The cutest addition to my Christmas decorations.

One of the most fascinating things I stumbled upon? An antique telescope from the East India Company, dating back to the 19th century. Just imagine the adventures it had seen!

Exploring Arezzo Beyond the Market

Beyond the antiques, Arezzo itself is a Tuscan gem. I wandered through its streets, discovering hidden courtyards, charming cafés, and beautiful Renaissance architecture. The Duomo di Arezzo was a highlight, with its stunning stained-glass windows and gothic interiors. And from behind the cathedral, I soaked in breathtaking views of the rolling Tuscan countryside.

What makes this market special is how seamlessly it blends into the historic cityscape. Unlike other markets, which are often tucked into squares or halls, Arezzo’s antique fair feels like it takes over the entire town, making the whole experience even more immersive.

As we drove back to Milan, our car packed with vintage treasures, I couldn’t help but feel grateful for such an incredible adventure. Between the breathtaking landscapes, the thrill of the antique hunt, and the magic of staying in a castle, this trip had it all.

If you ever find yourself in Tuscany on the first weekend of the month, the Arezzo Antique Market is an absolute must-visit. Whether you’re a seasoned collector or just love discovering unique vintage pieces, it’s an experience like no other.

Want to see the adventure in action? Watch the full video on YouTube here:

Arezzo Antique Market & Tuscany Travel Vlog.

Until the next adventure—happy thrifting and happy travels!