If you’re planning a girls’ trip to Tuscany, you couldn’t pick a more perfect destination. Picture vineyard-hopping through rolling hills, wandering charming medieval villages, and sharing long, laughter-filled dinners over wine and wood-fired pizza. Every other year, 12 of us—The Sisterhood—plan a big trip together, and this time, Tuscany delivered everything we hoped for and more.
Where we Stayed
After what felt like hours of scrolling through villa listings and comparing options, I stumbled upon Villa Caprile in Cortona—and I instantly knew it was the one.
It checked every single box: six bedrooms, six bathrooms, a private pool, outdoor dining, a pizza oven (yes, really!), and plenty of space for all 12 of us to relax, laugh, and make memories together.
From the moment we arrived, it just felt right. We spent our evenings outside under the stars—dancing, singing, sipping wine, and laughing until our cheeks hurt. The villa gave us the space to connect, unwind, and just be together, which is exactly what we wanted from this trip.
Not only was the house beautiful and comfortable, but the location couldn’t have been better. Nestled in the Tuscan hills just a short drive from Cortona, it was the perfect home base for our girls’ trip to Tuscany and all of our day trips around the region.
If you’re planning a girlfriends’ getaway (or any kind of group trip), I can’t recommend this villa enough. You can read my full review of Villa Caprile here.
Day-by-Day Itinerary
Day 1: Arrival Day
After months of planning and anticipation, the day had finally arrived and we were all on our way to Tuscany! Since we were coming from different cities, everyone made their own way to Italy and then to the villa. Slowly but surely, one by one, our group of twelve began to trickle in.
There’s always something special about those first few hours of a trip. There are hugs, the excitement of exploring your home for the week, and that joy of “we’re finally here!”
Villa Caprile did not disappoint. We spent the rest of the afternoon settling into our rooms, touring the grounds, and catching up by the pool. The views were incredible—rolling Tuscan hills in every direction—the villa itself felt like something out of a dream.
That evening, the villa’s caretaker, Anotella, treated us to a delicious, homemade pizza served al fresco. It was the perfect, low-key way to kick off the week……no stress, no rush, just good food, good wine, and great company.
It set the tone for everything that was to come—relaxed, joyful, and full of heart.
Not everything went exactly according to plan though. One of our girls had to miss the first day because her passport didn’t have six months of validity left. (More on that in the tips below—definitely double-check before you travel!).
And two others arrived around midnight and had a heck of a time finding the villa. It’s tucked away high up on a winding dirt road, and navigating it in the dark with spotty GPS wasn’t easy. After some panicked texts and a few missed turns, they decided to sleep in the car until morning—but lesson learned: arrive during the day if you can!
Day 2: FLORENCE
We decided early on that trying to navigate Florence by car sounded like a headache we didn’t want. So, we hopped on the train instead, and it was absolutely the right call. Taking the train to Florence was a breeze and gave us a chance to relax and enjoy the views.
The train ride from Camucia-Cortona station to Florence’s Santa Maria Novella (SMN) station takes just under 1.5 hours, and tickets are around €12 each way. They can be booked on Trenitalia.com.
Florence is one of those places that you could spend a full week in and still feel like there’s more to see, but with just a day, we hit the highlights.
We started at the iconic Duomo, and yes, we climbed all the way to the top! Climbing the Duomo was tough, but the breathtaking views made every step worth it. From there, we walked over to the Uffizi Gallery, where we lost ourselves in Renaissance masterpieces (hello, Botticelli and Michelangelo). After that, we crossed the Ponte Vecchio (new jewelry anyone?), browsed a few shops, and then walked through the Boboli Gardens to soak up some sun and serenity.
We ended the day with dinner at a cozy local trattoria tucked away on a side street. We came, we saw, we ate!
Day 3: CORTONA
We spent the day exploring the charming hilltop town of Cortona. It’s known for its rich history and stunning views of the surrounding Tuscan countryside.
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. The day started in Siena, one of the best towns in Tuscany and my favorite (with Cortona coming in a close second). On our girls’ trip to Tuscany, Siena’s 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 energetic vibe and lovely streets make it a standout day trip destination in Tuscany.
Next up, Wine (cheers and applause)! We made the 45-minute drive to the beautiful Poggio Rubino Winery for a bit of wine tasting.
If you’d like to enjoy lunch during your visit like we did, the winery offers a charming private tasting room. Here you can savor a delicious meal while taking in stunning views.
Then for our last stop of the day, we made the 1-hour drive to explore the medieval streets of picturesque Volterra. Volterra is such a gem in Tuscany. 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 featured in the Twilight saga as the vampire headquarters. So naturally, on our girls’ trip to Tuscany, we were on the lookout for any mysterious vampires! Thankfully all we found were 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. There was even and a handful that headed down the hill to Villa Piazanno for a cooking class. It was a fun mix of activities that suited everyone’s interests perfectly.
On every trip, we always set aside a free day like this. Whether that means relaxing, exploring on your own, or discovering new places at your own pace. It’s the perfect way to make your girls’ trip to Tuscany truly your own.
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 charming old 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 sipped on the rich Brunello, all while soaking in the beautiful 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. It’s just straight out of a storybook.
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.
When to Go
Spring (April–June) and fall (September–October) are ideal for Tuscany—mild weather, fewer crowds, and vibrant landscapes. Summer is beautiful but hotter and busier, especially in touristy towns.
Getting to Cortona and Getting Around Tuscany
Most of us flew into either Rome (FCO) or Florence (FLR), which are the two main international airports closest to Cortona. From there, the easiest and most flexible option is to rent a car and drive to the villa. Cortona is about a 2.5-hour drive from Rome and around 1.5 hours from Florence.
We coordinated in advance to land around the same time so we could group up and share rental cars. Splitting a car between 3–4 people made it more affordable. Plus, navigating those winding roads with a co-pilot definitely helps!
While you can technically get to Cortona by train (from either airport, you’d transfer to a train headed toward Camucia-Cortona station), having a car is honestly essential if you want to fully experience Tuscany. So many of the region’s best villages, wineries, and hidden gems are scattered across the countryside with limited or no public transportation. Being able to hop in the car and explore at your own pace made the trip way more flexible.
Also, a quick tip. If your villa is tucked up a hillside like ours, make sure your rental car isn’t too low to the ground. Some of those country roads can get a little… rustic.
Travel Tips for a Smooth Stay in Tuscany
Double-Check Your Passport Expiration
While Italy officially requires that your passport be valid for at least 3 months after your departure, many airlines enforce a 6-month rule, so it’s best to play it safe and renew early if you’re close to the cutoff.
As I mentioned, one of our girls had to miss the first day of the trip because her passport didn’t meet the airline’s requirements. Lesson learned—check early, and if you’re even remotely close to the cutoff, renew it!
Villa Tip:
Before you arrive, Antonella (the villa’s amazing caretaker) can do your grocery shopping and stock the villa with essentials. We sent her a list ahead of time—wine, snacks, breakfast items, and even ingredients for our first meal—and everything was waiting for us when we arrived. It made the first day so much easier and let us settle in without needing to run to the store. Highly recommend taking advantage of this option!
Splitwise – The Star of Group Travel
We used Splitwise to track shared expenses throughout our trip, and honestly, it was a game changer. With 12 of us in Tuscany, there were a lot of shared costs: dinners out, bottles of wine, gas, groceries, tips, taxis, and even a few spontaneous gelato stops.
Instead of trying to split the bill at every meal (which is nearly impossible with a big group), we alternated who paid and simply logged the total in Splitwise. The app automatically divided it evenly and kept a running tab of who owed what. You can even adjust for people who didn’t participate in a certain expense (like if only 8 of us went to a winery lunch).
- Keep your receipts and jot down any notes on the back—who paid, who was there, and what it was for. It’s a quick habit that makes logging expenses at the end of the day so much easier.
- Settle up at the end using Venmo or Zelle. Splitwise makes it super easy with a final tally for everyone.
Useful Travel Apps
A few good apps made our time in Tuscany way easier:
- Google Maps – Essential for navigating Tuscany’s winding roads and small towns. Download offline maps ahead of time so you’re covered even when cell service is spotty (which happens more than you’d think).
- Rome2Rio – Great for mapping out how to get from point A to B by train, car, or bus when planning day trips.
- WhatsApp – Most villas and local tour guides prefer communicating via WhatsApp, so it’s worth downloading if you don’t already use it.
- Google Translate – Helpful for restaurant menus or communicating with locals if your Italian is a bit rusty. You can even use the camera to translate text!
Pack Smart
Don’t overpack! Tuscany is stylish but relaxed. A few dresses, flat sandals, comfy outfits for day trips, and a light jacket or wrap for cooler evenings will go a long way. Bring a swimsuit for those villa pool days, even if you don’t think you’ll need one.
Bring Some Euros
Most places accept credit cards, but it’s always smart to have a bit of euro on hand. Things like parking meters, small shops, or that cute cafe often only take cash. ATMs are available in most towns, but they’re not always right around the corner.
Final Thoughts
With our fantastic squad, sun-drenched scenery, top-notch wine, and hands down the tastiest food ever. We all agreed, this was truly a once-in-a-lifetime adventure. There’s just something magical about Tuscany—the pace, the views, the wine, and the joy of sharing it all with people you love. Whether you’re planning your first girls’ getaway or your fifth, I hope this post helps you dream it up and make it happen.
What Now?
Looking for help getting started on a group trip? Here’s how to get started:
1. Start Your Group Chat:
Planning with a big group can feel like a lot, but get that group text or WhatsApp thread going. Share links, ideas, dates, and early “who’s in for a girls’ trip to Tuscany?” Pick one person to be the trip coordinator.
2. Pick a Home Base:
Cortona was perfect for us, but there are tons of great spots in Tuscany. Look for a villa with enough bathrooms (trust me), a pool, and shared living spaces where you can gather in the evenings. Having a beautiful, comfortable home base makes all the difference for your girls’ trip to Tuscany.
3. Get Transportation Booked Early:
You’ll want to rent cars. It’s smart to book those as soon as your flights are set, especially if you’re traveling in peak season. Coordinate arrival times so you can share vehicles and cut costs. It also helps to appoint a few drivers in advance so everyone knows who’s behind the wheel.
4. Book a Few Things Ahead:
Book pre-planned activities (like wine tastings or guided tours) in advance. Get Tours was a great option for us—they handled the driving and gave us local insight, which made our days even better.
And from there, it’s easy peasy. But if you still need help, feel free to reach out to me on social media. I’m always happy to chat travel. Don’t stress too much about the little details. Enjoy the planning process, embrace the adventure, and most of all, soak up every moment with your favorite people in one of the most magical corners of Italy. Your girls’ trip to Tuscany is waiting and trust me—it’s every bit as dreamy as you imagine.
Here’s the full itinerary in PDF Format:
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