A picnic table set under a vine-covered pergola, plates of fresh pasta soaked in olive oil and herbs, crisp white wine in my hand while gazing over the olive fields of Tuscany.
This picturesque, decadent scene was one I've dreamed of for many, many years. I've had this imaginary location percolating around in my head ever since I watched a travel show on the Tuscan countryside. This desire to feel at home in Italy and enjoying the many sights, tastes and emotions of Tuscany has been growing over the years. And as of May of this year, I can gladly say it has happened!
For my 29th birthday, Ryan wanted to take me to Tuscany. He knew how much I have been wanting to visit this part of Italy and he told me to plan out my dream Tuscan trip. With endless options at my fingertips, I scoured the internet, Facebook groups, Instagram pages and more trying to find the ideal location for our trip.
But here is the problem...
There is so much to see in this small region! The options are nearly endless and each town has their own specialty that you must try or a church you have to see. To say I was a bit overwhelmed would be an understatement.
So after several weeks of trying to find our location for this week-long trip, we opted for a road trip instead to try and see several major sights.
Frankfurt to Pisa to Florence
Since we had just recently moved to Germany, we flew from Frankfurt to Pisa through Ryanair. If you haven't heard of this budget airline just know its super cheap, super basic and expect long lines and fees for everything.
But you just can't beat $20 tickets so we were able to bring my mother-in-law with us and saved some serious $$.
Pisa wasn't our final destination, so we took a bus from the airport into Florence which was roughly an hour drive. There are stands located in the baggage claim in the Pisa airport where you can buy your bus ticket. We paid around 14 Euros per person and it was a very easy and comfortable trip to Florence.
The bus will drop you off near the train station and you can either catch a taxi or walk to your hotel/Airbnb. We decided to walk since we didn't have a car seat and it was one of the most exhausting parts of the trip. Our Airbnb was located about 25 minutes away and with a toddler, three duffle bags and two backpacks we were all tired and all a bit cranky. But the crankiness quickly subsided since we were in Florence and our trip to Tuscany had officially begun!
Florence - the city of art
Its as dreamy and culturally-rich as you would expect it to be.
Florence is the definition of elegance but not in a smug, aloof way. The people of the city know what a fantastic home they are blessed to have, but are eager to share the beauty and culture with those wanting to learn.
I was dying to get lost among the windy streets and massive buildings, meander over the bridges and take in the sights, smells and atmosphere of Florence. And we did just that.
Florence is a great city to visit with kids. The food is a toddler's dream (pasta, pizza, gelato, etc.) and most locals love little ones. Milena won the hearts of a lot of Italians during our time in Italy, especially in Florence. She would strike up conversations with the friendly locals and she got dozens of kisses during our time in the city.
We ate a lot of pasta, even more gelato and meandered through the streets while people watching. Our entire family had a great time and we wish we could've stayed longer.
Heading to the countryside
Italian cities have so much to offer, but our traveling trio prefers the quiet countryside. So after two days in Florence, we rented a car and headed south.
We decided to break up our road trip through the countryside and split our time between Campiglia dʼOrcia and Chianti. There is so much to see in Tuscany that we felt we should stay a few days in each location to get a feel for the different regions.
When I started to plan our trip, I was a bit overwhelmed on where to have our home base. There are dozens of quaint, Tuscan towns worth staying in and even more hotels and home stays. I had no idea where to start! So I took to social media and a few travel groups I am a part of to get a feel on where to stay.
Our family wanted two things:
stay on a vineyard to be able to taste the wine that we could see out of our window and;
stay at an agriturismo which is an active Tuscan farm and see firsthand how a Tuscan family lives.
Campiglia dʼOrcia
Through all of our digging and research, we came across a charming and affordable agriturismo in Campiglia dʼOrcia. Le Rogheta is situated far enough away from large towns but close enough to sight-see during the day. The agriturismo is run by an older couple whose roots run deep in Tuscan culture and they were so happy to talk with us about the history of their town and family.
Its a stunning property overlooking olive trees and offered our family a peaceful and unique experience in Tuscany. When we travel we love to feel what it would be like to live in the new location and Le Rogheta offered that for us.
And even better? They had a picturesque picnic table that was under a vine covered pergola that looked over the Tuscan countryside. It was every bit of my Tuscan dream that I could've asked for. We made fresh pasta, ate local cheeses and olive oil while drinking wine that came from the vineyard down the road. It was magical to say the least.
With Campiglia d'Orcia as our base for a few days, we took several day trips to surrounding towns and vineyards.
Castiglion d'Orcia
Our first night we planned a nice dinner out at Cisterna Nel Borgo which sits on top of a hill and was a perfect spot to capture a sunset. The food was traditional and delicious and it was first great stop in the countryside. The town is small and quaint. We felt full immersed with the locals and enjoyed meandering through the alleys which were quiet and quintessential Tuscan.
Bagno Vignoni
Little did I know, Tuscany is known for its hot springs. There are several popular spots throughout the region and a well known spa town, Bagno Vignoni, was close to our hotel so we stopped by for an afternoon. This small village surrounds a rectangular tank of water that has been used since the Roman times.
This spa was used by notable people throughout history and has been kept in great condition since the Medieval Ages. We ate pizza, drank wine and wandered through this quaint village.
One thing I fell in love with Tuscany is its relaxing and easy atmosphere. There is little stress which is always a breath of fresh air. Bagno Vignoni felt like it was still set back in time and the mood of the surrounding area was one of pure relaxation and bliss.
Pienza
By far, my favorite Tuscan village was Pienza. The entire town oozed Tuscan charm and I felt that we were walking through a movie set. Everything was so perfect and so perfectly Tuscan.
There are dozens of specialty shops selling anything from cured meats to Pecorino cheese (a local delicacy), olive oils to fresh pastas, dried mushrooms and even handmade leather goods. The shops line the streets and they beckon you to come in and spend your life savings in these beautiful Tuscan products.
Around every corner, the door steps became more and more beautiful and ornate. I filled my camera up with dozens of doors and flowers. I simply couldn't take in how beautiful every home was in Pienza. If it wasn't for our toddler's nap time we could have spent the entire day soaking in the beauty of this town.
Monticchiello
One thing you must do when visiting Tuscany is to simply drive. Its renowned for its its beautiful landscapes and the Italian cypress trees that line the winding roads. One of our most favorite days was hitting the road with the windows down and getting lost.
I joined a traveling Facebook group and Monticchiello was mentioned several times as a must-see town during a Tuscany trip. After about a 20 minute drive through some of the most beautiful vineyards I've every seen, we arrived at the hilltop town that gave an impressive view over the countryside. Cute little shops were nestled in the alleys and traditional Tuscan restaurants sat along the hill so you could have dinner with a view.
*Tip: make sure to book a reservation at the Osteria La Porta restaurant, a must see when visiting Monticchiello! We completely forgot to reserve a table and unfortunately were politely turned away.
Cappella della Madonna di Vitaleta
An iconic image for Tuscany, the Cappella della Madonna di Vitaleta is a small, secluded church hidden in the countryside. Located off a dirt road, a quick 10 minute walk got us right at the front of this beautiful church. Its simplicity is what makes this chapel so charming and it was worth fighting other tourists for a perfect picture.
Here is the location of Chapel Vitaleta
Siena
After spending several days in the Campiglia dʼOrcia area, we took our car north to our next destination, Chianti. However, on the way we were passing through Siena, a famous Tuscan city whose historic center has been named a UNESCO World Heritage Site. One of our friends who is from Italy always mentioned that Siena was her favorite Tuscan town so we knew we had to stop by and check it out ourselves.
Contrary to the previous towns we had visited in the countryside, Siena was grandiose and every bit dramatic. Siena is a medieval city situated on three hills with its center, the Piazza del Campo, the main attraction. Every summer, the famous Palio horse race is held in the Piazza which used to be the location of the Roman forum.
Hundreds of people, including our family, relaxed in the piazza underneath the red Palazzo Pubblico and its tower while listening to music or eating gelato. Milena enjoyed washing her hands at one of the fountains in the center and I could only think about how many people before her used this very same spout. Its pretty amazing.
Chianti
As we headed into northern Tuscany, the landscape changed from rustic to more polished vineyards and fields. Large agriturismos dominated the hilltops and there were dozens upon dozens of roads lined with Italian cypress trees.
Chianti was mentioned over and over as a great hub for a Tuscan vacation. Its location is perfect to once again take mini-day trips and the wine is incredible.
I was really wanting to stay on a vineyard and came across Agriturismo Casale Dello Sparviero. It was a former monastery that has since been turned into a vineyard and hotel. Situated on top of a hill, Agriturismo Casale Dello Sparviero gave us panoramic views of its vineyard and the Tuscan countryside. The best part was you get to have a free wine tour and tasting! We brought several bottles home with us.
The hotel was incredibly romantic, charming and only had a few rooms which gave us a quiet stay in Chianti. We were able to walk among the vines while sipping wine from these fields which added to the overall ambience.
Every evening we would make a plate of cheeses, bruschetta and pour some wine and sit underneath the trees of the estate. There are no words to describe how incredible it was to drink wine that came from the vines only ten feet away from us. Every sip I cherished and tried to mentally save the taste, smells and views of those evenings. And all I could think of was how perfect our entire road trip had been.
San Gimignano
San Gimignano is a small, yet very popular, walled medieval city which is commonly referred to as the Town of Fine Towers. I had heard of this historic town from several other bloggers and wanted to make the drive to see it in person.
The skyline of San Gimignano is unforgettable. Thankfully, the town has done an astounding job in preserving its towers throughout the years. Fourteen towers remain and which gave us a close up look to what Italian towns looked like in the Medieval Ages.
While it was packed with tourists and tour groups, we still enjoyed our time in San Gimignano. There are dozens of souvenir shops, gelato restaurants and local treats. I stocked up on some pottery and snacks to bring home with me.
Pisa
After our last night in Chianti, I will admit I was disappointed knowing we were leaving Tuscany the next morning. This once in a lifetime experience was coming to a close, and with the Tuscan wine still lingering on my lips we packed up our rental car and headed east to Pisa.
If you were to ask me before our trip if I every planned on visiting Pisa I would have bluntly said, "No. Sure, it would be cool to see the Leaning Tower of Pisa, but I have no interest." I wholeheartedly take back that wrongful opinion I had of Pisa.
The reason I was always so against Pisa was its unfortunate reputation. There isn't much to see, there are way too many tourists, it was so overrated, etc. etc.
These sentiments fill your screen if you type in Google "is Pisa worth visiting". I believe this reputation of Pisa was originated simply because other popular, Italian cities have so much more to see. However, that shouldn't stop you from seeing the iconic Leaning Tower of Pisa.
We were flying in and out of Pisa, so we decided to rent an Airbnb for a night and see this tower with its accidental tilt, and it is quite beautiful!
Located in the Cathedral Square, the Leaning Tower is the bell tower of the Pisa Cathedral and the entire square welcomes you with its white structures. The bright buildings are a bright contrast to the surrounding city and creates a regal-like atmosphere within Pisa.
Expect a lot of crowds and a lot of people posing like they are holding up the statue. Seriously. Nearly every person was taking this exact photo which makes a bit cliche, but its all in good fun. You can tour the Learning Tower and climb up the steps but we opted out.
Our family only spent about an hour in the Cathedral Square. So while Pisa does have some noteworthy architecture and history, I'm happy we only spent one day here during our Tuscany road trip.
There aren't enough adjectives I could possibly use to describe the beauty of Tuscany and the time we spent in the countryside. It was truly a dream vacation.
For the first time in my life, tears welled up in my eyes as I first viewed the rolling fields of olives and grapes. I honestly couldn't believe I was finally sitting under a vine covered pergola sipping on Chianti.
Some places are special for a reason, and Tuscany will hold a dear place in my heart as one of my favorite destinations to date. Our time spent as a family during this trip is irreplaceable and we truly fell in love with Tuscany and cannot wait to return.
“Italy is a dream that keeps returning for the rest of your life.” – Anna Akhmatova