Florence/Tuscany Region, Italy

Our son just graduated from the University of Michigan (Go Blue!), and to celebrate, we gave him the choice of a dream trip—anywhere in the world. His pick? The breathtaking Florence and Tuscany region of Italy! And wow… what an unforgettable experience!

From the moment we arrived, we were blown away. The rolling hills were a patchwork of lush green, the air smelled like fresh herbs and vineyards, and every turn revealed a postcard-worthy view. Tuscany’s beauty is the kind that just doesn’t translate fully into photos—but we tried! Scroll down to see some of our favorite snapshots.

And yes… we stayed in an actual castle (how cool is that?). Below the pictures, we’re sharing more details about this magical place, plus highlights from the historic towns we explored—like Florence, Siena, and San Gimignano—and of course, the incredible wineries we visited (because when in Tuscany… 🍷). Whether you’re planning a trip or just daydreaming, we hope this inspires a little wanderlust!

🏛️ First Stop: Florence

We kicked things off with a full day in Florence—and wow, did we put some serious miles on our tennis shoes! 👟😅 Florence is a beautiful mix of Renaissance history, world-famous art, and vibrant city life.

Here are just a few highlights we packed into our first 24 hours:

• Piazza della Signoria – An open-air museum filled with incredible statues, including a replica of Michelangelo’s David 🗿.

• Medici Riccardi Palace & Basilica di San Lorenzo – Key spots to understand the influence of the powerful Medici family.

• Medici Chapels (Cappelle Medicee) – Where the Medici rulers are buried, featuring stunning tombs designed by Michelangelo himself 😲.

• Cattedrale di Santa Maria del Fiore (Il Duomo) – The city’s most iconic church with its massive red-tiled dome. We climbed to the top and were rewarded with jaw-dropping views of Florence! 🏰

• Campanile di Giotto (bell tower) – More stairs… more amazing views.

• Baptistery of St. John – Known for its “Gates of Paradise” doors—true masterpieces in bronze.

• Galleria dell’Accademia – Home to the original Michelangelo’s David… and yes, he’s as impressive in person as you’d expect 💪.

• Uffizi Gallery – A must-see for art lovers, featuring works by Botticelli, Da Vinci, and Caravaggio.

We soaked up every moment before heading to what would be our home base for the next few days…

🏰 Our Airbnb CASTLE in Tuscany

Yes, you read that right—we stayed in a CASTLE! 👑

Our amazing Airbnb host, Pietro, welcomed us to Castello di Valle, which has been in his family for over 200 years. He gave us a personal tour of the historic wine cellar (you can see the HUGE old barrels in the pics!) and showed us around the 7-bedroom, 5-bathroom property. It sleeps up to 25 guests—so if you’re planning a group trip, hit us up for the details!

To surprise the kids, we worked with Pietro to bring in a private chef to cook our first dinner at the castle. Melissa coordinated the menu to make sure everyone had something they loved. We started (of course) with a glass of wine 🍷, followed by an unforgettable multi-course meal… topped off with a fire in the fireplace and—let’s be honest—another bottle of wine. 🔥🍾

🏰 Charming Towns, History, and Wine (LOTS of Wine)

🚗 Day 2: San Gimignano & Siena

• San Gimignano – Known for its medieval towers and charming squares. We loved Piazza della Cisterna, the Duomo di Santa Maria Assunta, and wandering the cobblestone streets.

• Siena – This historic city blew us away. We visited Basilica San Domenico, the Sanctuary of St. Catherine, and the gorgeous Piazza del Campo, home to the famous Palio horse race 🐎. The Duomo di Siena is a gothic masterpiece, inside and out. Plus… shopping and wine tasting? Yes, please! 🛍️🍷

🍇 Day 3: Wine Tour Day (Driver Required! 😄)Melissa hired a driver (thank you, Roberto! 🙌), so I could enjoy the wine without worrying about the roads. Best decision ever!

Here’s where we went:

1. Fattoria di San Michele a Torri – A beautiful estate where we learned about soil types, olive trees, and wine aging. They even had a wine gas station! Locals bring bottles to fill up on their favorite wines. So cool! ⛽🍷

2. Podere dell’Anselmo – Our absolute favorite!! Fabrizio, the owner (you’ll see him in our pics surrounded by 12 bottles 😆), was SO much fun—full of stories, knowledge, and charm. We laughed, we learned, and we tasted wine like pros. If you visit just one winery in Tuscany, make it this one! We seriously wanted to bring Fabrizio home with us to host tastings 🍇😂.

3. Tenuta Torciano – Our last stop (not that we needed more wine after Fabrizio’s flight of 12!). We tasted 10 more wines paired with an amazing meal. Then it was straight back to the castle for a much-needed nap. 😴🍝🍷

🏞️ Wrapping Up the Trip

Our final few days were just as magical. We explored:

• Montepulciano – Famous for its wine and hilltop views 🍷⛰️

• Pienza – A tiny gem known for pecorino cheese 🧀 and perfect Renaissance planning

• Montalcino – Home of the prestigious Brunello wine region 🍷

• Pisa – Of course, we took the classic “holding up the Leaning Tower” photo! 🗼😂

• Lucca – A walled city with quiet charm and great walking paths 🚶‍♀️🚴

We spent our last night back in Florence, did some final shopping, had a delicious farewell dinner, and got a few hours of sleep before our early flight home ✈️.

💙 Final Thoughts

This trip was, hands down, one of our favorite family vacations ever. Our son did an incredible job researching and planning it all—seriously, he could be a travel agent! 🙌

Driving in Tuscany was surprisingly easy (Florence… a little less so thanks to all the fearless motorbikes weaving through traffic 😅). But everything else? Absolute perfection.

If you’ve ever dreamed of visiting Italy—especially Florence and Tuscany—go! The beauty, the people, the food, the history, the wine… it all lives up to the hype.

We’re already dreaming about our return trip. Until next time, Italia 🇮🇹❤️