Planning a trip across the pond to Italy? I recently soaked up an incredible 7 days in Tuscany, Italy with my family, and boy, was it a whirlwind of pasta, vino, and unforgettable experiences. If you’re looking for a week of pure bliss, look no further than the rolling hills and charming towns of Tuscany. So, pour yourself a glass of vino and let me take you on a journey through the land of art, history, and indulgence.

DAY 1: GETTING THERE

Our adventure started with a hop, skip, and a jump from Denver to Rome. (There may have been some lost luggage along the way but let’s forget about that.) From Rome, we hopped on a train to Florence to get to our chariots for the week, aka our rental cars. Driving on the busy streets of Florence all the way to San Gimignano was a thrilling way to start the week to say the least, but we made it!

Where to Stay

When in Tuscany, do as the Tuscans do! We stayed in an incredible Tuscan villa, Rosso Fiorentino. It was our home away from home for the week, only better. With an outdoor pool, a view of Sam Gimignano int the distance, and an outdoor wood-fired pizza oven, it was the perfect home base to relax and explore nearby gems.

DAY 2: MONTALCINO

Let the grape adventures begin! On Day 2 we kicked off our Tuscan escapade with a scenic drive to Montalcino, where we landed at Podere Le Ripi for a wine tour. Sipping on vino while taking in the lush vineyard views was just what the doctor ordered. We had a private lunch in the tasting room above the wine cellar that I’m still dreaming about weeks later.

Then, with our spirits lifted (quite literally), we made our way to the captivating town of Siena. Trust me, you’ll feel like you’ve stepped into a time machine with all the medieval charm. The Siena Cathedral is an absolute must when you’re in town.

That night, just minutes from our villa, we went to Mormoraia agriturismo (a farmstay with a restaurant, lodging, and winery all in one place) recommended by our villa host. Everything from the food to the views to the wine was incredible – add it to your must-see list!

DAY 3: FLORENCE

On Day 3, we drove back to Florence for an entire day dedicated to the city of art, history, and drool-worthy food. Our day started with a food tour with Christy of Tuscany Flavor that set the bar HIGH. We explored a local market, tried paninis, chocolate, wine, and gelato all in a couple of hours. If you’re in Florence, this food tour is a must along with a stroll across the Ponte Vecchio and seeing Michelangelo’s David in person. If you have time, head to a historic wine window! This one had a line around the block, but it was worth the wait. Don’t feel like waiting? Head to the rooftop above Rinascente Firenze for drinks and a view of the Duomo.

DAY 4: SAN GIMIGNANO

Day 4 was all about immersing ourselves in the enchanting land of San Gimignano. It’s a teeny town but feels like walking through the pages of a storybook with cobblestone streets and charming shops. Pro tip: Keep an eye out for street cats—they add that extra touch of cuteness! I highly recommend grabbing a panini at Da i’Mariani for lunch or an afternoon snack. Dinner at La Vecchie Mura was the absolute highlight of San Gimignano. Make a reservation just in case!

DAY 5: LUCCA & PISA

Time for an adventure on two wheels! We headed to Lucca, a totally underrated gem, for a bikes and bites tour. Honestly, Lucca was the highlight of my entire trip. It felt like we were pedaling through history and the bike trail along the town’s medieval walls was a stunning way to see the city. On the way there or back, I recommend stopping at the Leaning Tower of Pisa just to see it. I was shocked at how breathtaking it was in person! That 3-degree lean is a sight to behold.

DAY 6: LIVORNO

After all this time landlocked in the rolling hills, we were craving water views on Day 6. We headed to Livorno, a port town that gave us serious Venice vibes with its canals and boats. The Mercato Centrale is worth a visit to try local food and grab a coffee to fuel up. For lunch, we found a restaurant with a floating dock right in the canal and watched the boats go by as we feasted on fresh seafood. I’m still dreaming about it!

On our last night in the villa, a private chef cooked our family one of the best meals we had all week right in our own kitchen. If you can, I highly recommend booking a chef during your Tuscany trip to have an authentic home-cooked Italian dinner experience!

DAY 7

On Day 7, it was time to bid farewell to Tuscany. We returned our rental car in Florence and hopped on a train back to Rome for a final hurrah. This was a whirlwind day of seeing as much as we possibly could in Rome. We hit all the must-sees—the Coliseum, Trevi Fountain, and the Forum—but the Coliseum at night stole the show. Talk about a dramatic exit!

So, there you have it—a week in Tuscany packed with pasta, vino, and unforgettable moments. Italy has a way of stealing hearts, and Tuscany is no exception. So, when you plan your own Tuscan escapade (and trust me, you will), be ready to fall in love with la dolce vita over and over again. Happy travels!