After the bustling energy and historic sprint through Rome, the second stop on our Italian adventure brought a welcome change of pace. Nestled in the heart of the countryside, Tuscany gave our family a chance to slow down, take a deep breath, and truly soak in the breathtaking beauty of Italy’s rolling landscapes.

If you are planning your own Tuscan getaway, here is our guide to where we stayed, our favorite day trips, and essential tips for making the most of your time here!

Getting Around: Why You Need a Car

Before diving into where we stayed, there is one essential thing to know: you really should rent a car if you stay on the outskirts.

While you can technically take the train between major regions, getting to rural towns or country estates requires a personal vehicle or arranging rides. Having our own car gave us total freedom to explore local spots on our own schedule, navigate scenic backroads, and take day trips without hassle.

Pro Tip: Make sure your rental car booking is sorted well before you arrive, and ensure you have local currency on hand for toll roads!

Where We Stayed: The Hidden Gem of Reggello

For our base in Tuscany, we stayed in Reggello at the beautiful Fattoria Degli Usignoli.

Reggello is a charming town situated just on the outskirts of local hot spots, making it a hidden gem for travelers looking to escape the heavy crowds and submerge themselves in true Tuscan culture. Surrounded by rolling hills, vineyards, and olive groves, it provides a tranquil setting while still serving as an ideal base for day trips to Florence and the Chianti region.

Our time spent directly at Fattoria Degli Usignoli provided some of our favorite moments of the entire trip:

• Horseback Riding: Exploring the countryside on horseback was an unforgettable experience for the family.

• Hiking: Easy access to trails right outside our doorstep allowed us to explore at our own pace.

• Olive Groves: Walking through the estate’s stunning olive groves offered a peaceful, quiet escape that allowed us to step away from screens, restore our spirits, and enjoy uninterrupted family time.

Quick NOTE: While the grounds were absolutely stunning, the sleeping accommodations did not impress as much. Unfortunately, the beds were not that comfortable. I wouldn’t say it was horrible, but I do think it is worth noting.

Highlights & Day Trips

While our base was peaceful, we made sure to balance our downtime with some incredible day trips across the region.

1. Leaning Tower of Pisa & Piazza dei Miracoli

Visiting Pisa was a truly fun day out! And yes—the lean is just as obvious in person as it looks in photos.

Of course, we had to snap the classic family photos “holding up” the tower, but exploring the surrounding Piazza dei Miracoli was just as wonderful. Standing together beside such ancient, iconic architecture is always awe-inspiring, no matter how many times you’ve seen it in pictures.

Pisa is so much more than just a tower or structure or place to take a clever picture. The surrounding area is absolutely beautiful and rich with history. I am so glad we took time to enjoy

2. The Ferrari Museum

Even though we are seriously unlikely to ever own a collection of iconic vehicles (or even a single one!), we couldn’t pass up the chance to visit the Ferrari Museum while staying so close by. It turned out to be fascinating and a highlight for everyone. This is definitely worth adding to your itinerary if you’re traveling through the region. I mean you can dream, right?!

Quick Tips for Your Italy Trip

To help you prepare, here are a few quick practical tips to keep in mind (including a few carry-overs from our Rome guide that are just as crucial here!):

• Bring Cash (Euros): Cash is king for highway tolls and parking meters. Many places we visited did not accept credit cards.
• European Adapters: Pack wall adapters compatible with European standards so your devices stay charged.
• Passport Safety: Keep a clear photocopy of your passport saved in your email or printed at home as a secure backup.
• Language Assistance: Download Google Translate ahead of time. While tourist hubs have English speakers, many locals in smaller Tuscan towns do not.
• Dining Schedules: Italian breakfasts are light (usually just a coffee and a pastry). Keep in mind that many restaurants do not open for dinner until 7:00 PM—plan afternoon snacks accordingly if your family prefers eating earlier!
• The “Pizza Rule”: Proceed with caution when ordering pizza! In many places, toppings are added after the crust is baked, which can leave you with cold toppings on a warm crust.

Final Thoughts

Tuscany delivered the perfect balance of iconic sight-seeing and meaningful family connection. Whether we were marveling at Pisa, admiring supercars, or riding horses through olive groves in Reggello, it was a stop on our Italy trip that we will cherish for years to come.

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Happy FunCycling Friends,
Sarah ; )

Because home is where peace begins.