In the summer of 2016, right after graduating from college, I took a two-week backpacking trip through Italy with one of my best friends, Jamie, from junior high school. Before I started blogging, I usually would journal my travels, and still I do. So, right form the pages of my journal, these are my adventures in Italy…

Day One:

After a very long flight and a 5 hour layover in London, we touched down in Rome around midnight. We took a bus, walked the rest of the way to our hostel and crashed for the night. Sleeping was not so much fun thanks to the boy in the hostel that snored like a freight train.

Since we planned to take on Rome during our last few days, we got up early in the morning and headed to find the bus station and make our way to Florence. We spent €1.50 and took the underground to the bus station. After getting lost for a moment, and my failed attempt at speaking Italian to ask for directions, we managed to climb aboard the right bus.

The ride from Rome to Florence is beautiful. Once you get out of the city there is nothing but vineyards, hills, farmland and houses built of orange clay.


We arrived in Florence just passed 12 in the afternoon. When we hopped off the bus it was drizzling out, so we ducked for cover while dodging people trying to sell umbrellas. We set out to find a map of the city to find directions to the Piazza della Signoria, where we would be meeting our horse riding and wine tasting tour in Tuscany, that we had booked before arriving.

Once we bought a map we walked through the cobble stone streets of the city. Florence is filled with old, compact streets that seem to go on in never ending spirals. It has a pleasant, relaxed feel to it.


Later that evening, I was going to meet up with a friend, Pip, who was doing an internship in Florence at the time. Strangely enough, as we were walking around, we turned the corner and we actually walked right into her. We introduced our friends to each other a caught up for a bit. It worked our pretty well, she had some time to show us a bit of the city. As we made our way through the streets we learned about the history and it’s architecture.


She took us to the Piazza della Signoria and showed up the fake “David” (the real one is in one of the museums) and all the statues in the plaza. Most of them are about horror stories and/or Greek mythology and all are original.



When Pip had to go, Jamie and I had an hour left until our tour, so we headed to the famous bridge, Ponte Vecchio. The streets to get there were filled with people selling African bracelets and Italian paintings. We made our way past the tourist to the river and actually could not figure out what bridge it was for a few minuets… but after turning in circles for a few times, we figured it out.


After the bridge we grabbed street sandwiches for €3.00 and headed to our meeting spot for the tour. Everywhere you go in Italy you can find large sandwiches being sold. They are filled with thin slices of meat and cheese and are very cheap for the size.


We met up with a handful of others, all American, and followed our guide down the bumpy streets to a white van. Like all vehicles in Italy, the van was tiny. Due to the small roads, Vespas or small cars are used most often. I don’t think I saw one pick-up truck the entire trip. Our group was very chatty and everyone was kind, we had some great conversations throughout the tour.

Once we climbed in the van we were on our way to Chianti. The drive itself was beautiful and also quite scary… It was about a half hour from Florence to our destination. Not even five minuets passed before we were out of the city and driving down long, windy roadways with nothing but vineyards and old, large houses scattered throughout the countryside. Many of the roads were obviously made for one car at a time. Thus we all though we were going to hit another car each time one passed, or that we were going to fall off the hillside.


Tuscany is like every photo I have ever seen of this beautiful country. With rolling hills of green and grape vines in long rows, it makes you feel like you were transported to the past. It did not disappoint.

We arrived at the barn, signed wavers, greeted the horses, then went to saddle up. The horses were already tacked up and waiting for us outback. When they asked us about our riding experience, I made the mistake of telling the owner that I teach horseback riding, and was given the most difficult horse. I kid you not, he bucked several times on the trail, was spooked by a deer, could not keep his footing up or down hill and kept trying to trot when he heard our guide say anything… I did not think I was not going to survive that ride.


Regardless, riding through the vineyards of Tuscany was breathtaking. We rode up and down the hills, through the grape vines and olive groves. The ride lasted about an hour and I did not want to dismount.


When we got back to the barn, we all dismounted and mingled with the horses for a bit. Everyone was freaking out about my horses behavior, which was funny now that it was over. But I thanked him for the ride and gave him a treat anyhow.


Taking our time, we boarded the van again and set off. We got to stop off at a grape vineyard to take photos and walk through the rows. Our guide talked about the vines and how wine is made. Unfortunately, the grapes were not in season, so we did not get to try any.



Once again we got back into the van and were off. Our next stop was at a home that belonged to a family of winemakers. The house was high up on the tree covered hills. To get there we had to take a very steep, unpaved path. The family not only owned a small vineyard, but a small farm as well, with pigs, ducks, donkeys, dogs and lots of cats. The home itself was very old and had a porch/terrace that overlooked the landscape.


It was a bit strange being there because while we tasted their $800 wine, the family was hosting a sleepover for the children who had just finished school. I did not favor the wine (too bitter for my taste) but I loved seeing the family interact. It felt like a sneak peak behind the scenes of the locals of Chianti.

When we left the home we went to our final destination, which was the headquarters of the tours. We parked and walked up the hill to the old wine distillery (now used as the head quarters) and were given a small tour. We were shown old wine presses and fermentation tanks and explained how the wine was made.



We then took to the main room for dinner. We sat at a long table under a low ceiling made of stone. The table was littered with wooden plates filled with cheese, thinly sliced meats and tomato on bread. We were given several different samples of wine to taste- none of which I liked and promptly poured into Jamie’s glass. (What can I say, I like my wine sweet.)


We were also given 10 year aged vinaigrette and olive oils to try. I was not the biggest fan of those either. However, everyone at the table seemed to love them. We were asked to help ourselves to the spread of traditional Tuscan foods that were laid out for us long a high table against the wall.


Everyone tried everything. There was bread, thin sliced ham and salami, cooked and raw veggies, lots of tomatoes, a pea and carrot dressing mix, and a delicious dish of beans and sausage. There was two different pasta dishes, eggplant and a sweat pea dish. I loved almost everything, and it was one of my favorite meals while in the country.


After dining for a long while, we packed up and headed out. We arrived back into the city of Florence around 8:30pm, just as it was getting dark. After saying goodbye to our group and thanking our guide, we headed back to the Piazza to meet up with Pip.


We met in front of a fountain, caught up, then headed to a local Irish pub to grab a drink and relax. After, we walked around the city for a bit.


I was on the search for gelato. Luckily, the place I was looking for turned out to be Pips favorite place, “La Carraia”. It was the best gelato I had in Italy! I recommend the dark chocolate and the hazelnut. It is only €1.00 per scoop!

After walking around some more, we stopped into another local place call “Kuskuu” (I think?). They serve you popcorn while you are waiting. I placed an order for a drink that I thought was fancy, but turned out to be pineapple juice with ice… oh well!

Soon after, we said our goodbyes and headed to our bus. The one thing I learned from the day…When booking tickets be very careful with your times, especially if you are not accustomed to military time, because you may accidentally book your tickets for the previous day. Which I most defiantly did. However, I quickly went on my phone and ordered tickets for the correct trip.

We climbed aboard our overnight bus to Milan, leaving Florence and Tuscany behind us.




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