Under the Tuscan Sun: Our Italy Itinerary
After celebrating my 40th birthday at Borgo San Felice and along the Italian coast, we knew we had to return to Italy… but this time with a focus on wine country. And oh my goodness, did Tuscany deliver. From the rolling hills and storybook villages brimming with old-world charm to the food, the wine, the friends, and the laughter… it was the kind of trip that settles deep into your soul. We left a few pieces of our hearts in Cortona, no doubt about it.
Our villa was chock full of charm and character… surrounded by picturesque grounds, complete with a pool I had to be physically pried away from. The interiors were rich with history and rustic elegance, comfortably housing our group of four couples. With concierge service on hand (shoutout to Johnny for helping plan the most seamless itinerary), the entire experience felt effortless and oh-so-special.
It’s nearly impossible to choose a favorite moment, because the whole trip was a highlight reel. But if you’re twisting my arm, I’d say the e-bike wine tour followed by a beautifully curated lunch might take the top spot. Then again, the Mediterranean coast was pure magic. So was dinner at Il Falconiere. And don’t even get me started on the wine pairing at Cantina Canaio. The Tuscan countryside truly is as dreamy as they say.
Sharing our full itinerary below… plus my packing list for those of you dreaming up your own Tuscan escape.
DAY 1
We arrived in Rome on Saturday, picked up our rental cars from Sixt, and made a quick pit stop for lunch and gelato while waiting for the rest of our group to land. From there, we drove to Cortona and checked into Villa Garavaglia. That first evening, we headed into Cortona village to indulge in pizza, wine, and (of course) more gelato… because when in Italy, right?
DAY 2
On Sunday, we kicked things off with a slow villa morning, breakfast courtesy of Chef Marcia (who absolutely spoiled us all week). Most of the day was spent poolside soaking in the sunshine. That evening, we dressed up for dinner at the Michelin-starred Il Falconiere… an experience I’ll never forget.
DAY 3
On Monday, we enjoyed another delicious breakfast at the villa before setting out for a full day of winery tours in Montepulciano. Our stops included La Braccesca and Cantina Canaio, where we enjoyed the most delicious wine-paired lunch overlooking the vines. Dinner that night was in Cortona at La Loggetta, tucked in a charming village square.
DAY 4
Tuesday was unforgettable. We took private e-bike private tours through the Tuscan countryside… rolling hills, vineyards, wildflowers… and ended with lunch and a wine tasting at Poggio Sorbello Winery. That evening, we kept things casual with a pizza party by the villa pool.
DAY 5
Wednesday took us to Siena for a guided food and wine tour arranged by our villa concierge. We made sure to pop into local favorites like Antonio the Butcher and Nino and Friends for the best bites and treats. That evening, we returned to the villa for a hands-on cooking class, which made for such a fun, cozy night in.
DAY 6
On Thursday, we headed out to the coast for a boat tour of Porto Ercole with Bryant Wood from The Travel Boutique… the sparkling water and coastal views took our breath away. We enjoyed dinner back in Cortona at Caffe Del Torreone (easily the best pizza everrrr) with live music made for a perfect summer night.
DAY 7
Friday… our final full day was intentionally left open. The girls spent the morning shopping in Cortona while the guys visited the Gladiator filming location. We regrouped for a slow dinner at Bistrot agli Amici, soaking in our last golden evening in Tuscany.
DAY 8
Saturday came too soon, and after a bittersweet farewell to the villa and our friends, we headed home… our hearts full, our bags fuller, and our souls deeply touched by the magic of Tuscany.
If you're planning your own Italian getaway, I’ve included my Tuscany packing list below! I hope this itinerary inspires your own unforgettable adventure.
