7 Italian Cities in 6 Nights

I am the epitome of the phrase, “doing the most.” This can be both a good thing and a bad thing when it comes to vacations. I like to make the most out of short trips. I like short trips because that means less PTO used. Less PTO used means I can save days for future trips.

So, when I went to Italy this past May for just six nights, I made sure to plan to see as much as I could. My original list consisted of 9 Italian cities, but when I arrived to Milan and waited 2 hours for a rental car, I knew things wouldn’t go exactly as planned. However, I was able to explore seven wonderful cities as described below.

Day One: From VA to Milan to Montecatini

We arrived at the Malpensa Airport in Milan in the early afternoon. From there we would drive to a small town called Montecatini located in the Tuscany region. The drive would take about 3.5 hours and I had hoped to stop by Parma or Bologna on the way for a bite of traditional Italian food. Unfortunately the rental car process was a mess, which gave us no time to make any stops.

I took on the challenge of driving in a foreign country. To my surprise, it actually wasn’t bad. The “speed limit” was faster than I’m used to at a whopping 130 kmph (80 mph). The views during the road trip made the time fly by. I was in awe at the stunning landscape and disbelief that I was actually in Italy.

We arrived in the adorable town of Montecatini where we stayed at Hotel San Marco for five nights.  Although a little dated, the hotel was great including friendly staff, free parking, and free breakfast. The nearest train statin was just an 8 minute walk away. The central location of Montecatini was ideal to do day trips to different cities by train. We grabbed a late dinner then called it a night to prepare for a full day of exploring.

Day Two: Cinque Terre

I woke up bright and early eager to begin my first real day in Italy. The beautiful Cinque Terre was our destination for the day. I wrote a full post on this gorgeous region, so I won’t spend too much time writing out the details. (Be sure to check out the post here)

Prior to my trip, I came across so many photos of these colorful buildings amongst the deep blue waters. I knew that I HAD to visit during my time in Italy. I absolutely loved Cinque Terre and all it had to offer. Whether you wanted to partake in outdoor activities or relax by the beach, there was something for everyone. I took advantage of both.



I hiked from Riomaggiore to Manarola, which was strenuous, beautiful, and fulfilling. The views you’re able to witness on this hike is simply indescribable. You HAVE to see it for yourself. After the solo hike, I met up with my three friends in Manarola for lunch. Once we were done devouring delicious Italian sandwiches (paired with wine, of course), we headed to the beach in Monterosso.

The wait for the next train sure was a memorable one. A conversation with one of the workers was immediately sparked. This older gentleman was so friendly and engaging. He asked for my nationality in which I responded Vietnamese. He was in complete shock, telling me he had never met a Vietnamese person before. He proceeded for about 15 minutes – spilling out all sorts of compliments and telling me I could find a nice Italian guy and stay there forever. Talk about a confidence booster! He asked for a photo and although initially hesitant, I obliged. We all definitely got a kick out of the situation.

We finally boarded the train to Monterosso. There we were able to just relax by the beach and soak in the sights. The water was still way too cold to take a dip though. About an hour later, we hopped on a train to La Spezia to ensure we’d catch the last train leaving to Montecatini. Be sure to keep track of the train departure times!

Day Three: Chianti

The Greve in Chianti is located only an hour from Montecatini by car. This day was by far the most memorable and exciting part of my trip. Check out my previous post where I go into full detail about wine tasting in Chianti.


The wine completely wore us out by the end of our second vineyard visit. My original plan was to head down to Sienna after our wine tastings, but quickly learned that was not possible. I believe everyone (except for the driver) passed out as soon as we started the trek out of the Chianti region.

When we got back to Montecatini, we all agreed it was time for a much needed nap. After a few hours of sleep, I forced myself out of bed for a late night meal. We walked around the town and came across a bar owned by a Norwegian gentleman. He spoke perfect English, so it was extremely easy to communicate with him. We ordered drinks and steaks to fill our stomachs up. As much as we wanted to stay out late, we were all still exhausted from our adventure in Chianti. So, shortly after we finished our dishes we headed back to the hotel to get a full night’s rest in preparation for the next day.

Day Four: Venice

Oh the magical city called Venice. Surrounded by waters that is said to one day take over the city, Venice is a must see. Although I’ll be completely honest, I found that there really wasn’t much to do there. Now, I will admit that I didn’t research everything or branch out to other areas besides San Marco. But my take was that a lot of the stores were more or less the same. I believe one or two nights in Venice would be plenty of time to explore the whole city.

We arrived by train and then took a water taxi to where our Airbnb was located. Now I will say that the atmosphere was wonderful. The streets were booming and you could always hear an Italian man singing on a gondola. Our Airbnb apartment had a stunning view of the canal. It was pretty surreal.


After we settled in the apartment, we scavenged for a lunch spot. The possibilities were endless. However, beware of restaurants’ sitting fees! Do not get scammed into paying more than you have to. We chose Kori, where I indulged in a perfect plate of spaghetti with clams. My best friend, Daniella, still talks about the pizza she ate there. She exclaims that it was the best she’s ever had (FYI: she’s a pizza fanatic & connoisseur).

After our stomachs were full and happy, we went back to the apartment to get ready for the night. Of course, the first activity on our list was a gondola ride. Yes, I know…huge tourist attraction, but it’s worth it! It really is necessary to do this at least once when visiting Venice. It’s all part of the experience although a bit pricey (around $40/person). You get spectacular images from rowing along the canal and wonderful photo ops. Need a new profile picture? This is the perfect opportunity!

After we finished our gondola ride, we ventured off to explore the nightlife of Venice. Well, the nightlife is pretty much nonexistent. There weren’t many bars around and most places closed early. We ended up at an Irish pub? Grabbed a few drinks before heading back to the apartment to conclude the night.

The next morning we had pizza and pasta for breakfast, shopped around San Marco, and then headed to the train station for our next destination.

Day Five: Florence

I’ll admit right now that I regret not spending more time in Florence. This city is filled with history and culture. We arrived to Florence by train from Venice around 3:00PM. As soon as we arrived, I instantly fell in love with the city. For some reason it reminded me of New York City, but with a traditional look. The roads were bustling and the streets were filled with restaurants and shops.


Our first stop was the infamous Duomo di Firenze (cathedral).Remember to abide by their dress code when entering. Although unable to go to the top (best to book in advance), we were able to explore the inside. Every single detail put into the construction of this beautiful church was incredible. I stood there in admiration.


The museums in Florence are closed on Mondays, of course the day we visit. So be sure to keep that in mind when planning out your trip. That did not prevent us from having an amazing time though. We grabbed a quick bite to eat after exploring the Duomo. What I love is walking around the city and being able to turn into any street and stop by a restaurant without having any previous knowledge of the place, and yet you’re not disappointed. I had the most amazing caprese salad. One of the dishes I miss most from Italy.


After our quick bite with the accompanying glasses of wine (always), we were ready to explore more of Florence. My friend Joe’s old classmate, Molly, actually lives in Florence so we were able to meet up with her. It was so nice to be able to have someone there with us who was familiar with the city and spoke the language. Since we were there for only 7 hours, it was critical that we didn’t waste any time.

We walked through the Piazza della Signoria, which is a huge open space with artwork placed all around. It is known as the political hub of the city. Then we walked along the Arno river to get a view of the Ponte Vecchio, also known as the Old Bridge.

We walked across the bridge as Molly gave us amazing information about the culture and lifestyle in Florence. We were beginning to run out of time, so decided to grab dinner together instead of going to the Piazza del Michelangelo. We ordered these Aperol spritzers, which are apparantly the rave in Italy. After my first sip, I could tell why these orange drinks were a hit! Delicious, refreshing, and strong. We got a round and then ordered a carafe of red wine as well to pair with our meal. Molly and I decided to share a margherita pizza and risotto. Just typing this is making my mouth water. I crave authentic Italian food regularly.

Our 7 hours in Florence were up soon after dinner, so we headed back to the train station. My advice to everyone is to spend more time in Florence! I’d estimate two nights minimum to explore everything this amazing city has to offer.

Day Six: Pisa and Milan

And just like that our trip was coming to an end. On day 6, we checked out of our hotel in Montecatini. It was time to say goodbye to this adorable little town in Tuscany. We quickly grabbed coffee before driving to Milan for our last night in Italy. We also planned to stop by Pisa to see the leaning tower since it was on the way.


Pisa was extremely easy to get to. Prior to our arrival, I looked up parking lots to park our car. I found one, which was extremely inexpensive, and walking distance to the tower. There are a lot of people on the streets of Pisa trying to sell stuff. I tried to avoid contact as much as I could. Also, be very cautious of pick pocketers. Pisa is known for this especially since it is such a huge tourist attraction.

We probably spent no more than 20 minutes in Pisa. Besides the tower, there didn’t appear to be much to do there. After taking plenty of photos, we continued on our route to Milan. And no, I didn’t attempt to take a cool photo holding up the tower in some way. I know, boring.


We arrived in Milan in the evening and immediately checked into our hotel, Hotel Ibis Milano Malpensa. This hotel is located near the airport, which is about 45 minutes away from the actual city center of Milan. The city center has limited driving zones, so I looked up metro stations and parking outside of the city to avoid the chaos. The metro system is extremely easy to navigate, so I’d definitely recommend doing that. We got off at the Duomo stop, which drops you off right in the middle of the city center and directly in front of the Duomo. We only had a few hours to explore Milan.

We hung out around the Duomo for a bit before venturing off to the shopping plaza. A shopper lover’s paradise. Of course, you’d have to break the bank for those stores. A bit too high end for my taste, so we were proud window shoppers instead. We got amazing gelato from Cioccolati Italiani. The perfect ending to my gelato tour in Italy. Then we walked around to find a place to eat dinner. It was our final real meal, so we decided to go all out and ordered so much food. I got beef carpaccio and mushroom risotto paired with a carafe of red wine (big surprise, right?).

Next thing I knew, we were signing the check and heading out the door. We caught the last metro out of the city and back to the car. I drove us to the hotel where we got our final night of sleep in this absolutely amazing country. Although my friends were beginning to get home sick, I was yearning to stay even longer. I was not ready to head back to the states as there was so much more that I wanted to see. Unfortunately, that was not an option for me and I boarded the flight back to Virginia the next morning.

Italy was as amazing, if not more, as I had ever imagined. The food, the culture, the people, the history, the scenery, the wine, it was all unbelievable. I’m so glad I was able to visit those 7 cities listed above, but I will definitely have to return to explore more of this beautiful place.

If you have any questions about traveling to Italy, please leave a comment below!

Italy Vlogs


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