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  • Writer's pictureChristine

Our Italian Adventure - Tips & Tricks For Exploring Italy!

Italy! It's a country where you can find ancient history and art, rolling countrysides and urban cities all within a few hours of each other. After not traveling to Europe since the spring of 2019, we were long overdue for a trip, and our 14 days in Italy did not disappoint!

While the reason for going to Italy was seeing The Cure on my birthday in Milan, the concert was just a small piece of the trip. We started the trip in Milan, made our way down to Florence, drove through the Tuscan countryside, and ended in Rome.

As you can see, I was pretty excited to see The Cure in Milan!

As always, I have some great tips to share with you and I'll break it down into each stop we made. So keep reading if you are planning your own Italian adventure!

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Honestly, Milan was our least favorite stop on our trip. While the city was beautiful and easy to get around, we found the people to be a bit rude. Think NYC in Italy - heads down, walking fast, and a bit aggressive.

Arriving In Milan

We flew into Milan and arrived at the Malpensa Airport. The airport was very easy to navigate, and outside of a glitch with the automated machines while we were in line, getting through customs was easy.

Tip #1: We took the Malpensa Express train to get to our hotel in central Milan. The train takes about 40 minutes and runs regularly. You can purchase your tickets at a ticket machine at the airport or online (click the link above). The train will take you either to the central train station (Milano Centrale) or a metro station downtown.

Where To Stay

We stayed at the B&B Hotel Milano Sant'Ambrogio, which is a 5 minute walk from The Last Supper. It was about a 10 minute walk from a metro station, which allowed us to easily get to other places in the city. The hotel was reasonably priced and the rooms were clean and well furnished.

What To See

The two major sites to see in Milan are the Duomo and Leonardo da Vinci's "The Last Supper".

Tip #2: You will need to plan well in advance if you want to see The Last Supper during your visit - particularly if you are going during peak travel season. Timed-entry reservations are mandatory, and they can sell out in minutes, months in advance. The easiest way to purchase your ticket is on this website. The site will tell you when they will be releasing tickets for your dates. Tickets are released and go on sale at noon local Milan time, so you'll need to get up early to grab tickets. You can book a time with our without a tour. I would suggest booking the tour if you can. It was well worth the extra money and only takes about 90 minutes in total.

You can also easily visit the Lake Como area from Milan. Plan on spending a full day to allow yourself travel time and a chance to visit several of the towns on the lake.

One of the beautiful villages around Lake Como.

Tip #3: We took the train to Varenna from Milan to get to Lake Como. You can catch the train from Milano Centrale, but note that it is NOT one if the regional trains, so you can't purchase your ticket from the red machines you'll see everywhere. To purchase a ticket, either go online here, or look for the Trenitalia ticket office.

Tip #4: The easiest way to get between different towns is by boat. There is a ferry that runs all day long mid-lake. We purchased the all day pass, which allowed us to take as many rides as we wanted in between each town.

Our favorite area in Milan was the "Little Venice" area. It's a great spot with lots of cute bars and restaurants along the water. You really can't go wrong with any of the restaurants there, but I would suggest stopping at La Vineria before dinner for a glass (or two) of wine. They serve their wine their directly from the tanks and it's delicious! It's also a great spot to sit outside and people watch while enjoying your glass of wine.

The "Little Venice" area was our favorite part of Milan!


After not really caring for the vibe in Milan, Florence was a welcome change! The city is very walkable. After arriving, we didn't feel the need to take the metro or tram to get anywhere we wanted to go. We had three nights in Florence and definitely felt like we would have liked to have one or two more.

Arriving in Florence

We took the train down from Milan and arrived at the Florence central train station - Santa Maria Novella. The train station is just a 10 or 15 minute walk from the central part of Florence near the Duomo.

Tip #5: While we call the city "Florence", Italians call it "Firenze". So don't be confused when reading signs or purchasing train tickets.

Where To Stay

The place we stayed in Florence - La Residenza del Proconsolo B&B - was probably my favorite of the trip. The location was absolutely perfect - we could see the Duomo from our window. And the room was huge! Note that you do have to go up some stairs to get to your room and there is no lift.

Tip #6: I love to stay at locally-owned hotels in Europe rather than big chains. But keep in mind that the locally-owned hotels typically do not have a front desk that is operated 24 hours a day. So, be sure to contact the hotel prior to your arrival to arrange for a check in time. Also note that your hotel might be located within a larger building and have an outdoor entrance that requires a key (yes, an actual key) to enter. For most of our hotels on this trip, we had to carry around 2 or 3 keys - one for the outer door, one for the entrance to the hotel, and one for our room.

What To See

Florence is an art lovers dream! It's packed with so many different museums, that you could spend a week doing nothing but museums. The Uffizi Gallery is one of the most famous museums in the world, and contains the greatest collection of Italian paintings anywhere.

Even if you don't take the time to go to any museums, all you have to do is walk around Florence to see amazing art. Walk inside any church you come across, and you'll find some of the most beautiful paintings. Take a stroll through the streets and you'll see amazing sculptures everywhere.

Tip #6: For some of the best views of the city, go to Piazzale Michelangelo. The hike up to the top is not for the faint of heart, but once you get there, the views are totally worth it. It's on the other side of the Arno River, so you can see the entire city from above.

While my husband didn't love the hike up to Piazzale Michelangelo, he agreed the views were worth the climb!

If you have the time, a day trip to Pisa and Lucca is quite easy from Florence. You can grab a train at the central train station. It takes just over an hour to get there, and if you manage your time correctly, you can do both towns in the same day.

You should visit Pisa once to see the leaning tower, but it's a once and done day trip.

Tip #7: To see both Pisa and Lucca in the same day, here's my advice. Grab a train in the morning to Pisa first. Take a walk through town and grab some lunch to go as you walk to the Field of Miracles. The area around the leaning tower is VERY touristy and crowded. We were quite happy to just see the leaning tower from the outside, grab our pictures and go. From Pisa, you can grab a train or bus to Lucca (the train ride is only 15 or 20 minutes). Spend your late afternoon/evening wandering around Lucca and grab a drink before catching the train back to Florence. If you grab a train at 6 or 7 heading back, you'll still have plenty of time to grab a late dinner in Florence.

Where To Eat (And Drink)

We honestly did not have one bad meal during our trip, but Florence was probably the star of the show for food. Here are a couple of my suggestions.

Ristorante Natalino: This was not only the best meal of the trip, but it was one of the best meals we have ever had. While the food was simple, it was still so unique and absolutely delicious. The service was top notch. We got lucky and just walked up and were able to get a table outside on this lovely corner where the restaurant was located. And the prices are very reasonable.

All'Antico Vinaio: For one of the best sandwiches you'll ever have, check this place out. They now have locations in New York and Los Angeles as well.

Tip #8: We had multiple people recommend All'Antico Vinaio to us, so it is definitely a big attraction. In fact, we were told to expect to stand in line over an hour. We went on a Monday at around 11:30 a.m. (which is very early for lunch in Italy) and walked right up, but a line was already starting to form by the time we finished our sandwiches around noon. When you get there, you'll see that there are a couple of shop fronts. They are all the same and serve the same food, so just pick the one with the shortest line. They do not have seating, so it's grab and go.

These sandwiches were amazing! Definitely worth standing in line for!

Move On: For a fun twist on a bar, check this place out. The first level is a bar, but the second level is a very cool record store. They have lots of great music memorabilia throughout the building. They also have some great outdoor seating right near the Duomo and really delicious drinks.

One of the coolest things we did on our trip was a private cooking class with Paola Migliorini. Paola is an expert on Florence and Tuscany. In fact, she is one of the people that helped Rick Steves write the Florence portion of his Italy guidebook. For our cooking class, Paola had the two of us over to her flat, and she and her daughter helped us cook a full meal in her kitchen. Paola does lots of different tours and I highly recommend her. Check out her website for more information.


While wine is produced everywhere in Italy, the country is probably most famous for its Tuscan wine region. The easiest way to get around is by car. We rented a car in Florence, and it was an easy drive to arrive in the heart of Tuscany.

Where To Stay

Tuscany is a large area with several small towns interspersed throughout. We used Montepulciano as our home base, which is one of the biggest of the towns. We stayed at Vicolo dell'Oste B&B, which was a lovely place that was centrally located, and had the sweetest owners that were extremely attentive and helpful.

Tip #9: For most of the hotels in town, you cannot park your car there. Public parking is located at the bottom of a very steep climb to get to the town center and your hotel. So be prepared for a climb with your luggage, and likely some steps to climb up to your room.

The scenery is amazing, but be prepared for your car to be parked way down there!

Tip #10: This area is very tourist dependent. At peak travel times, the area is very crowded. While we enjoyed missing the crowds, there wasn't much to do after 9 or 10 p.m. during the off season. In addition, we just happened to hit a week that was between an Italian holiday at the beginning of November and the opening of the Christmas markets at the end of November. The owners of our hotel told us that many people take their own vacation during this time, so it was a challenge to even find an open restaurant in the evening.

What To See

Grapes, of course! The area is packed with vineyards. It would be impossible to visit them all. In order to maximize your wine experience, I would recommend booking one tour/tasting at a vineyard. We visited Altesino, which was beautiful and gave us a nice tour and tasting.

You should definitely pick at least one vineyard in the Tuscan countryside to visit and do a wine tasting!

To have the opportunity to taste wines from many different wineries, just pop into a wine bar in one of the towns. We found two great places that both have the mechanical dispensers that give you a wine card with credits on it. You select the wine you want to taste, insert your wine card, and push the button to pour. In Montalcino, check out Enoteca di Piazza. In Montepulciano, take a walk up to the Fortezza Medicea and you'll find another wine bar with mechanical dispensers and amazing views!

One of the wine dispenser machines in a wine bar in Montepulciano. Wine please!

Where To Eat

We had two great meals in Montepulciano. We had one of our most unique meals of the trip at La'Altro Cantuccio Ristorante. This place was all about the presentation, so your meal was a complete culinary experience. A little pricey, but well worth it. For a more rustic experience, try Rosso Rubino Trattoria. It's a tiny place owned by a husband and wife. She runs the front of the house and he cooks the food. Delicious meal and great service!

Tip #11: I highly suggest making reservations in advance for any restaurant in the area. The restaurants are open limited hours for dinner and have limited seating. Even though we were there during off-peak travel time, we needed a reservation to get in both places I mentioned above. The owners of our B&B graciously called for us to make the reservation, which was a big help!


We absolutely loved Rome! Rome gives you all the advantages of a big city - lots to do including a great nightlife. But because Rome is made up of lots of smaller neighborhoods that each have their own feel and vibe, you still feel like you are in a smaller Italian town.

Arriving In Rome

We arrived in Rome by car, since we had rented a car to drive through Tuscany. We returned the care at Termini Station (the main train station). To say that we were happy to drop the car off after trying to navigate in Rome would be an understatement. We flew out of Fiumicino (aka Leonardo da Vinci) Airport, which is the larger of the two airports. Note that the airport is outside of the city, and you want to give yourself plenty of time to get there with traffic. We took a taxi, as it was the quickest and easiest way to get there. It's a fixed fare of 48 euro for a taxi from central Rome to the airport.

Where To Stay

Because Rome is quite large, location is key when picking a hotel. We stayed at the Hotel Paba, which was a fantastic location. It was just a five minute walk to the Forum, and still made it easy to get to all of the other sites we wanted to see. The hotel is located on the second floor, but there is a small lift so you don't have to carry your suitcases up the stairs. The rooms were clean and well furnished. And the owner, Alberta Castelli, was the sweetest lady! It's unbelievable how much energy she has!

What To See

There is a lot to see in Rome! To get in everything comfortably, you need at least 3 full days.

Tip #12: I would suggest breaking up your visit as follows... Day 1 for the Forum and Colosseum. Day 2 for the Pantheon and other miscellaneous sites. Day 3 for Vatican City.

Rome is full of ancient sites, and the two most prominent (and popular) are the Colosseum and the Forum. Because these are the main attractions in Rome, they can be very crowded. Even during the "off-season", there were a lot of people packed in - particularly at the Colosseum. I purchased a combo ticket online in advance, which not only gave us a timed entry reservation for the Colosseum, but let us access the Forum and Palantine Hill at our leisure (tickets are good for 24 hours). Tickets can be purchased in advance here.

Be prepared for big crowds at the Colosseum!

Tip #13: When visiting the Colosseum and Forum, wear very good walking shoes. In addition to the steps and hills, a lot of the areas you are walking on are cobblestones and not easy to navigate.

Vatican City is another major tourist attraction. While St. Peter's Square and the Basilica are free to see, you must purchase a ticket to go into the Vatican Museums and see the Sistine Chapel. We chose to skip the museums, but if you do go, be sure to purchase tickets online in advance here.

Tip #14: If you choose not to do the museums and just go into the Basilica, you will likely need to wait in line to go through security to get in. We first arrived around 11:00 a.m., and the line was quite long. As soon as we approached the area, someone tried to sell us an "official tour", which promised to bypass the line. DO NOT FALL FOR IT! These are at best, private tour companies who don't have any way to get you in faster. At worst, they are just scammers. We decided to walk around the area and have some lunch, and then returned to the Vatican around 2:00 p.m. By then, the line had gone down quite a bit, and we only waited about 20 minutes to get in.

Tip #15: When you visit Vatican City, be sure to check out the Mercato Trionfale. It's a great market that locals shop at. While there really isn't any prepared food to eat, there are plenty of stands with fresh vegetables, cheese and meats.

You can buy wine "by the litre" at the market!

There are plenty of other sites throughout the city to check out, including the Pantheon, the Spanish Steps, Trevi Fountain, and lots of beautiful squares tucked within the city. It's worth taking a day to just wander around and hit those sites.

We always find that a great way to discover a city and meet some fellow travelers, is to do a food and wine tour. In Rome, we booked the Trastevere gourmet food and wine tour with Devour Tours, and really enjoyed it.

Tip #16: I would recommend spending at least one evening in the Trastevere neighborhood. There are lots of great restaurants and bars in the area, along with some cute shops. It's out of the main touristy area, so you will get a feel of a real Roman neighborhood.

Where To Eat (And Drink)

You really can't go wrong in Rome. Here are a couple of my suggestions:

Enoteca L'Angolo Divino: If you love wine, you need to check this place out. They have so many wines, that they hand you the almost 100 page wine list in a binder (the "wine bible"). And if you get overwhelmed by all the choices like I did, owner Massimo Crippa (who is also a sommelier), will be happy to help you make your selection.

The "wine bible"! So many choices!

Open Baladin: If you love beer, this is the place for you. Open Baladin has lots of craft beers from all over Italy on tap. And while we didn't try them, their burgers looked delicious!

L'Antica Birreria Peroni: And while we are talking about beer, you can't go to Rome without visiting the home of Peroni beer. The beer is delicious and so is the food. And it's very reasonably priced.

Tip #16: Be sure to pay attention to restaurant hours when planning your meals in Rome. Italians tend to eat their meals a bit later, and I found that to be even more so in Rome. Lunch usually happens mid-afternoon. Pre-dinner drinks happen around 5 p.m. or so. Dinner typically doesn't start until 7 or 8 p.m. at the earliest.

Italy In General

In general, we really enjoyed our time in Italy. We found that, particularly in the bigger cities, most Italians spoke English well, and it was easy to communicate with only knowing some basic words in Italian. Italy is on the euro, so currency is easy if you are used to traveling in Europe. While the trains were on time, efficient and cheap, I did find the train stations a little more confusing than in other parts of Europe (although I might have just been a little rusty from not traveling).

I found it quite reasonable to travel in Italy. We only paid, on average, around 100 euros per night for our hotels, all of which were quite nice. Some of this was likely due to the time of year we traveled, as I'm sure they are more expensive during peak travel season. All of our food and drink was also very reasonable.

We will definitely be back to Italy. For the next trip, I'd likely start in Rome and work my way to southern Italy to check out some new areas.

For now, arrivederci and happy traveling!

Have you been to Italy? If so, share some of your tips! Comment below or e-mail me at

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