Anyone who knows me knows I absolutely LOVE a girls’ trip! There’s truly nothing that feeds my soul more than spending time exploring a new corner of the world with ladies that I adore.
Every other year there are 12 of us who vacation together. These adventures are always eagerly anticipated, filled with laughter, exploration, dining, shopping, and simply enjoying each other’s company.
THE DESTINATION
When it came time for us to decide where to go for our biennial trip, Tuscany was the clear favorite, so I got to planning!
THE VILLA
After browsing through countless home rental sites searching for the perfect villa, I came across this gem in Cortona.
I really can’t say enough great things about Villa Caprile. To read more about it, see my detailed write up about it here.
With six bedrooms, six bathrooms, a pool, alfresco dining, a pizza oven, and lots of space to relax in our down time, it ended up being the perfect place for us to enjoy our time together. We spent several evenings in the outdoor space, belting out tunes, busting out the dance moves, enjoying some vino, and sharing in endless laughter. Not only was the villa pure perfection, but the location was the perfect jumping off point for exploring the many towns of Tuscany.
DAY TRIP ADVENTURES
Day 1: ARRIVAL DAY – Everyone arrived in Italy and made their own way to the villa. We spent the remainder of the afternoon/evening hanging out at the pool and acquainting ourselves with the villa. The villa caretaker prepared dinner for us.
Day 2: FLORENCE – Rather than drive our rental cars, we opted to take the train which was a great decision. We spent a fabulous day exploring all of the highlights of Florence.
Florence is an absolutely beautiful city that you could easily spend a week or more exploring. If, like us, you only have a day, here’s how I’d suggest you spend it: Start with a visit to the iconic Duomo and climb to the top for breathtaking views. Wander through the Uffizi Gallery to marvel at Renaissance masterpieces, then stroll across the Ponte Vecchio. Take some time to relax in the Boboli Gardens before finishing your day with a dinner at a local trattoria.
Day 3: CORTONA – After sleeping in a bit, we made our way to Cortona and spent the day exploring this Tuscan gem. Old Town Cortona is an utterly charming spot that feels like stepping back in time. Its narrow, winding streets are lined with centuries-old buildings and cozy cafes.
We loved the relaxed vibe and soaking up the stunning views and the friendly atmosphere. The town’s rich history is evident everywhere, from the ancient city walls to the beautiful churches scattered around.
For foodies and shoppers, Cortona doesn’t disappoint. There are quaint restaurants offering everything from fresh pasta to local wines, and shops filled with unique crafts and local goods. The whole place is just simply lovely.
After an afternoon of exploring and shopping, our evening was filled with laughter and a delicious dinner in the intimate private dining room at La Buccacia.
Day 4: SIENA, VOLTERRA AND WINE TASTING – We booked Get Tours to be our escorts today. We started in Siena, one of the best towns in Tuscany and my personal favorite (with Cortona coming in a close second). Its medieval charm is unmatched, with winding streets that lead to the stunning Piazza del Campo, where you can relax and enjoy the lively atmosphere. The Siena Cathedral and the city’s historic buildings add a touch of grandeur to the experience.
For dining and shopping, Siena is fantastic. The restaurants serve up delicious Tuscan cuisine, and the local shops are perfect for finding unique crafts and tasty treats.
Siena’s vibrant vibe and its rich history make it a standout day trip destination in Tuscany.
Next, we headed to the beautiful Poggio Rubino Winery for a bit of wine tasting.
We also enjoyed lunch with a view in this fabulous private tasting room.
Next, we were off to explore the medieval streets of picturesque Volterra. Volterra is such a gem in Tuscany, with its winding streets and stunning views that make you feel like you’ve stepped into another time. The medieval charm and scenic spots make it a must-see. We loved wandering through its quaint squares and soaking up the atmosphere.
And here’s a fun tidbit: Volterra was famously featured in the Twilight saga as the vampire headquarters. So, while we were eagerly on the lookout for any mysterious vampires, we only found amazing local food and breathtaking views—no bloodsuckers in sight!
Day 5: ON OUR OWN – Today, we decided to do our own thing. With some of us having visited Tuscany before and others here for the first time, it felt right to let everyone explore at their own pace. A few folks returned to Cortona, some ventured out to Orvieto, others lounged by the pool, and a handful of us headed down the hill to Villa Piazanno for a cooking class. It was a fun mix of activities that suited everyone’s interests perfectly.
DAY 6: MONTEPULCIANO, MONTALCINO AND PIENZA – We were thrilled for another day of exploration, and once again, we enlisted Get Tours to guide us. Our first stop was Montepulciano, where we wandered through its enchanting Renaissance streets. We enjoyed a cheese tasting that was a real treat, sampling local varieties that made us all wish we could take some home.
Next, we headed to Montalcino, a place we’d been eagerly looking forward to for its famous Brunello wines. We delighted in tasting the rich Brunello, all while soaking in the stunning vineyard views. The relaxed, welcoming atmosphere of Montalcino, paired with its breathtaking landscape, made sipping wine here feel like an absolute dream.
Our final destination was Pienza, a picture-perfect town with elegant architecture and charming shops. I can’t even express how absolutely charming this town is. We spent the remainder of the afternoon browsing through boutiques and picking up some gorgeous table linens. The blend of Pienza’s sophistication and small-town warmth made it a wonderful conclusion to our day’s adventures.
BUCKET LIST EXPERIENCE
With our fantastic squad, sun-drenched scenery, top-notch wine, and hands down the tastiest food ever, we all agreed—it was truly a once-in-a-lifetime adventure.
Looking for help getting started on a group trip to Italy? Check out our Italy Two-Week Travel Itinerary.
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