Home Travel How to get lost in Italy

How to get lost in Italy

by Out and About Mag.

Step one: Research all the cities you want to see in Italy.

Step two: Make an impossible list of ALL the things you want to do in Italy. 

Step three: Arrive in Italy and throw away your list. 


I wanted to explore Italy on my own terms. I wanted to get lost in this country. I wanted my visit to be intentional but sporadic at the same time. I had 21 days to make this experience authentic and meaningful, so when I arrived in Rome, I discarded my list and went with my gut. I had to discard the preconceived order of things that I wanted in order to enjoy the journey instead of being fixated on checking things off on a list. I prepaid for my hotels in Rome, but I cancelled other hotels in certain areas and literally booked hotels based on places I wanted to go. With my new itinerary, I could trust the travel gods to lead me in the right direction. My list included Sorrento, Capri, Naples, Positano, and the entire Amalfi Coast. However, on my second day in Rome, I knew I could only do one part of Italy, so I chose the North; Florence, Pisa, Venice, Siena, Milan and Lake Como. 

The best advice I have for virgin travellers to this country is to listen to local people or, if you have friends who have been to the country before, take any and all advice seriously. While purchasing your first train ticket in the heart of Rome, as soon as you choose the language to make the purchase, the kiosk recording actually says, “Beware of pickpockets.” I think that being aware makes it easier to avoid unpleasant situations. I was very careful where I placed my bags and even more careful about what was in my peripheral vision. Another good piece of advice is to not pay for private transportation to populated areas when trains and buses can take you there for a fraction of the price. For instance, taxis are convenient but not cheap. I paid 48 euros for my ride from the airport. Trains to and from the airport are 14 euros. I paid 13-18 euros for each trip to central Florence before I learned how to ride the local transportation for two euros. Local buses and light rail trains are the cheapest and day passes are the best value. You can travel within the country to almost any major city in Italy for less than 99 euros by train. I can attest that the coach seats on the train feel exactly the same as first-class and business seats. 

Surprisingly, you can be your own travel agent for Italy. You just need a good sense of who you are and a general idea of things you want to do. For example, if you are a wine connoisseur, a history buff, or a lover of art and architecture, Italy has everything you could desire. Use third-party hotel booking websites that provide free cancellations and NO deposit to book hotel rooms. Befriend a local merchant. In a few of the older boutique hotels I stayed in, you have to return your hotel keys when you leave for the day. While exchanging my keys, I rambled excessively what I wanted to see while in Rome. For instance, I knew that the Colosseum in Rome was the first thing on my agenda. The locals were quick to advise me to stay clear of scams, tourist traps, fake leather shops and inflated local restaurant prices. They told me where the best cafes are and the less expensive ways to “taste” local wines without paying for a glass. There are multiple tour companies that provide you with any type of tour you desire; walking tours, skip-the-line tours and exploration to parts unknown tours. Rome was not built in a day, but you can definitely see most of it in a van with air conditioning if you so choose. If you are a planner, there are many websites where you can book tours ahead of your trip. Or if you’re a last-minute Betty like me, you can walk up to any kiosk and book a tour. If your list includes the Vatican, the Sistine Chapel, Pompei, or Naples, there are specific tours or bulk tours that can get your boxes checked. Be prepared for long lines, the wait and vagrants that want to sell you everything! For foodies, you will love the idea of cooking classes which are like pop-up shops, so check the web or ask a local for the best ones in the area. 

Nightlife in Italian culture all depends on what you desire. I passed several nightclubs where you could hear music from a mile away, but I prefer drinking wine in cafes and bars after a night at the theatre at St. Mark’s Church hosts La Boheme, Madame Butterfly, Carmen, and other favourites playing May through October. Prices vary and can run up to 100 euros depending on the seats. I attended a ballet in the city for 25 euros. The following evening, I was serenaded by the Three Tenors in the Auditorium of Santo Stefano al Ponte Vecchio, an old church converted into a theatre east of Florence. I splurged on front row VIP seats for 55 euros and was actually selected for an impromptu waltz by one of the lead opera stars! It was the highlight of my weekend. 

To sum up my 21 days of exploring Italy, I got everything I wanted even if it was not on ‘the list.’ I enjoyed the impromptu experiences the most. I ate the best food Italy has to offer, rode trains through Bologna, Padova, San Giovanni and collected more sunsets from my hotel balcony in Florence. I cancelled my hotel in Milan because the Italians said that, “Milan is for shopping, not for a visit.” My last lesson to share is to come to Italy with a plan but be prepared to deviate from that plan. I was glad I discarded my list because just like my friend said, “You have to visit Italy in parts, and you have to go more than once! Because there is so much to see, you will get lost.” I was glad I made the trip and can’t wait to get lost in Italy again sometime in the future. 


Firenze, in Italian, is the place where you get the best of both worlds. You see an immaculate city sprawled between amazing hilltops, while the rolling countryside is half an hour away. In one bus ride, you find the best vineyards, hiking trails, ancient ruins, church cathedrals, or seascapes this country inhabits. I judge the life of a city by the heartbeat of its city centre. The busier and more crowded the centre, the stronger the heartbeat. Once you arrive, you will quickly feel the vibration beating in Pienza! 






Tuscany is a must for any traveller simply because it represents what locals call “Old Italy” while new cities like Milan are more modern and upbeat. If you are a “lazy” traveller like me, I enjoy long walks and bike tours that engage me in the best view of the mountains, green trees and vineyards. Travelling with an asthma pump, antihistamines and nasal spray is what kept me stable enough to enjoy trees stoked inside the mountains. Living in the desert for four years, you forget what green looks like. The vistas of the mountains that backdropped the clouds and a pristine blue sky were worth the risk of an allergy flare-up for me.

Siena is a small village in Tuscany, and I was drawn there by befriending a local cook at my hotel. She described it as an old town with fewer people. She almost made me think it was a secret village when she whispered it to me over breakfast. I spent less than six euros on a bus tour and was glad I listened that morning. The greenery literally takes your breath away. Pisa is not as elaborate as Florence or Rome, but if the Leaning Tower of Pisa is on your list, then, by all means, get your obligatory picture holding up the tower. It costs extra to go into the tower but again it’s up to you and what you want from the experience. I wasn’t at all interested in getting the picture that 1.3 million tourists get every year. Instead, I opted to get the best gelato and buy a new bag. 

The village of San Gimignano is a Medieval town tucked quietly in the heart of Tuscany. If you love history and antiques, this will be a good place to shop. Most of your tour guides are multilingual but check the fine print to make sure before you book. 


Venezia in Italian was an optional excursion before I arrived in Italy. Due to preconceived images in my head, I thought I already knew what was there because of television and movies I decided to take the train for a day trip and confirm what I already thought I knew. I’m proud to confirm that my suspected images were correct. Venice is magical! When I first arrived, I saw the most beautiful cathedral right next to the train station, the Church of Saint Maria (La Iglesias de Santa Maria de Nazaret.) I went inside to understand what the lines were for and the architecture, the paintings, the crisp spiritual statues of the Arch Angels made me gasps and swoon. Although it could have been the heat, I still say it was the beauty of the building that gave me life. 

The city on water is epically breathtaking! Transportation around the city varies, but it is the best way to get a complete visual of Venice. The gondolas are private tours, water taxis take you to specific places, while water buses take large groups to general locations around the city. Do what fits your budget and tastes. I landed inside a café by the centre, where I had the best lasagne of my entire life. Most times, we are underwhelmed when reality meets anticipation, but for this city in the sea, I was not disappointed. 


The best scenery I was enamoured within northern Italy was a city along a lake, Lake Como. I was lost in the mountains by the lake. You would find yourself distracted in this city, not knowing where your time went. For example, I went to Bellagio for a quick lunch and day trip. The ferry ran every hour; some ran every half an hour. I squandered the day before I realised that I only had two ferries left to catch before it was dinner time. I missed one trying to purchase souvenirs, so I sat by the water in a hook around the hill from the ferry stop. I gazed a long while before realising that 45 minutes had passed, and my ferry was about to depart. It’s that easy to get lost in the cinematic beauty of the lake. Visiting is a must for travellers who want a break from the big, fast city. 




I was not excited to leave Lake Como. Maybe it was the sadness of it being my last three days in Italy that broke me or maybe it was just getting lost in downtown Milan. I spent my last day in Italy crying in a metro station because I wasn’t on the right train. The lost in translation conversation steered me towards the wrong stop in the wrong direction, so I went one hour trying to find my way back to Central Station. I am usually very confident and travel savvy, but it was hot, I was tired, and I didn’t eat breakfast that day. I don’t think my neurons were firing correctly. I cried for almost fifteen minutes before a bus driver gave me the “correct” route to get back to the middle of the city. The moral of this encounter is that you have to pay close attention to details before you leave your comfort zone. Research your maps, train schedules and bus routes options before checking out of your hotel. Get all your train tickets and flight info before you pack and have to drag your luggage and hour and a half in the wrong direction in the middle of a hot Italian summer.

I love Italy. Ciao 


Kendria R. Johnson is a teacher, traveller, public speaker, author, mother and life coach. 

Her mission in life is to motivate, to inspire, teach, and to leave this as a legacy. A recently self-published author, her memoir, “Fat Meat Ain’t Greasy,” tells the story of her strength, struggle and strives for achievement. 

“I want my life to mean something and to let anyone who knew me understand God and the power of His love through my time here on Earth. 


Related Articles

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Read More