*If you sign up for Airbnb using my referral link you will get up to $50 USD off your first stay, and $15 to use toward an experience worth $50 or more, and I will receive up to $20 travel credit, at no extra cost to you!
“Not boasting but I head to Paris on Friday night. Then Italy. Happy Birthday to me.”
It’s not everyday you receive a message like this, especially from your dad who has never been to Europe. In mid September he announced he would be visiting Paris and multiple Italian cities over his birthday week. And instantly I was taken back to my time in Italy.
Read about my experiences in Italy!
When I visited during my honeymoon in the Summer of 2017 it was also my first trip to Italy. I spent a whirlwind week traveling through the country, eating my weight in pasta and watching my history books come alive. The country is filled with beautiful views, amazing food and stories of generations past. So how do you decide on what to see while there? It’s impossible to see it all.
The best destinations for your first trip to Italy are a mixture of big cities, and smaller towns, but they all have one thing in common: you will not regret adding them to your itinerary! Here are recommendations from both my dad & I, based on our own experiences!
Table of Contents
Cinque Terre
Top Sights:
Monterosso: This is the first or the last of the five towns, depending on where you are coming from. On my honeymoon we took a train in from La Spezia, and rode all the way to the furthest town, Monterosso. You can buy a Cinque Terre Train Card to get access to the trains, walking trails and buses in the towns.
The town is the perfect spot for swimming, although it can get quite busy on the beaches. My advice? Instead of finding a spot on the sand, walk further out onto the rocks and enjoy a more private access of the water from there.
A beautiful Summer day in Monterosso Al Mare
Vernazza: The town located next to Monterosso, this was my favorite of the 5 towns. The colors are spectacular: the houses are an array of different hues and the water is the most beautiful blue.
There is a cave that leads to a beach, and a harbor lined with restaurants and opportunities to jump in the water (if you’re a strong swimmer, as the water can be choppy).
The harbor in Vernazza
Manarola: This is the town with the iconic view of the colorful houses perched atop cliffs. You can watch people diving off cliffs into the water, or get lost strolling the streets.
Looking out at Manarola
Where To Stay:
You can choose to either stay within the towns or travel to them during the day. With the train system and the walking paths, it is easy to take a day trip or two into the towns. If you aren’t so worried about being budget conscious, being in the center of it all is an immersive experience.
I stayed at this Airbnb in a small town, located about 30 minutes outside of La Spezia. Although that meant we had to drive and then take a train into the towns, the experience staying with a family in the quiet mountains was one I would not trade. My dad stayed in a hotel right by the beach in Monterosso al Mare. Having more time in the towns meant spending a dinner in Manarola eating linguine with sea bass, complemented by wine, and getting a full body massage on the rocks of Monterosso.
*If you sign up for Airbnb using my referral link you will get up to $50 USD off your first stay, and $15 to use toward an experience worth $50 or more, and I will receive up to $20 travel credit, at no extra cost to you!
My dad’s hotel in Monterosso
First Trip To Italy Truthful Traveling Tip:
Spend more than one day exploring these towns. Although the trains make it easy to hop from one to the other, there are also amazing walking paths linking them, and so much to see in each town. I missed out on exploring the towns to their fullest because we had a single day to get through all of them.
Pisa
Top Sights:
Leaning Tower of Pisa: Yes, this is one of the most touristy things you can do in Italy. But yes, it is still cool! There are a million photos of people squeezing the Leaning Tower of Pisa between their index finger and thumb, making it appear small. And there are a million more of people pushing the tower back up to an upright position (like my dad!) It still is a beautiful structure, and you can enjoy it from the outside, or buy a ticket to climb to the top.
Typical tourist pose in Pisa!
Where To Stay:
This is a very small area, and again can be enjoyed in an afternoon. Staying in Florence would result in an hour commute to the East, and staying in La Spezia (train access to Cinque Terre) would be an hour commute to the North. My advice? Visit Pisa in between visiting Cinque Terre and Florence!
View of The Leaning Tower of Pisa
First Trip To Italy Truthful Traveling Tip:
Enjoy this university town! Pisa has many university students, as many significant higher institutions of learning are located here. One of them, University of Pisa, has been around since the 14th century. You will see many youth around the town, with smiling faces and laughter everywhere.
Florence
Top Sights:
Accademia Gallery: There is arguably only one reason to visit this museum: Michelangelo’s David. Sure, you can see a replica in a town square, but I promise you, it is not the same.
The detail in the famous sculpture is best described in another one of my posts: “It is a piece of magic that uses proportions and lines and details and science of the human body to transform a piece of marble into a realistic looking human.” The museum houses other Florentine paintings, as well as more of Michelangelo’s work.
Michelangelo’s “David”
Uffizi Gallery: The Uffizi is the larger museum in Florence, and is dedicated mainly to works of the Renaissance. The building itself is huge, and a tour definitely helps you to navigate your way around finding the most pertinent pieces of art.
We only had one day in Florence, and so we decided to take a full day tour. Our afternoon was spent walking around this museum, with a guide leading us to some cool views of Ponte Vecchio, many familiar works of art, and some unexpected ones, such as an unfinished painting by Da Vinci.
Ponte Vecchio from The Uffizi
Santa Maria del Fiore Cathedral: When you see a picture of Florence it probably includes the Duomo. Specifically, the dome. Designed by Brunelleschi, it stands out in the city. The exterior of the building is impressive. There are so many fine details, with even doors depicting scenes.
Unfortunately during my time there I did not get a chance to view the inside, as it was closed for church services. I have heard that climbing the steps of the dome gives you a pretty amazing view of the city.
The Duomo of Florence
Where To Stay:
Florence is not a huge city, so when we visited we saw no need to stay right within the city center. We found many cheap Airbnb options to choose from, that were located in Florence. It was a 15 minute drive to get close to the main center, where parking was a bit of a hassle.
My dad visiting the Duomo
First Trip To Italy Truthful Traveling Tip:
Plan your trip according to when sights will be open. We missed out on entering the Duomo because it was Sunday morning, and church services were being held. The two main museums, the Accademia and the Uffizi, are both closed on Mondays.
Rome
Top Sights:
Colosseum & The Roman Forum: There is no place like the Colosseum and the surrounding Roman Forum. Throughout my time in Rome I got to see the Colosseum lit up at night, empty, and got to explore it in the dry heat of the day.
The Roman Forum is filled with treasures. There is a new structure everywhere you look. The Arch of Constantine outside of the Colosseum stands bigger than imaginable. In the Forum, there are columns, there are temples that still retain their original colors, and the stories behind each landmark are centuries old.
The Roman Forum
The Vatican: Although the home base of the Pope and the Catholic Church is technically its own city state, it is within Rome. There is so much to see within the Vatican City walls, that you could easily spend days there.
The Vatican Museums house beautiful maps from the 16th century, famous Italian paintings, and ornate ceilings that represent Popes of the past. The Sistine Chapel has the world’s most glorious ceiling, and St. Peter’s Basilica has an Altar unlike any other I have seen.
Paintings in the Raphael Rooms at the Vatican
Trevi Fountain: Outside of our tours, we roamed the streets of Rome later in the evenings. One of the best decisions we made was to visit the Trevi Fountain at night. Although it was still busy, the crowds were small enough that you could enjoy the fountain.
Trevi Fountain
Rome is filled with fountains, and I was not ready for the masterpiece that is the Trevi Fountain. It is massive! And the details are so intricate (do you see a pattern yet, all of Rome is intricate!) I would recommend taking your own time to fully appreciate it. It is worth your time.
Another trip to Trevi Fountain where it was less crowded
Where To Stay:
Rome is a very walkable city, and the closer you can get to all the action the better. Although The Vatican will require a metro ride, many of the Roman sights are located in close proximity to one another. We stayed at an Airbnb that was located a 15 minute walk from the Colosseum. It was located right near a metro station, which, although it was closed for renovations, would have given us easy access to The Vatican otherwise.
The Colosseum lit up at night
First Trip To Italy Truthful Traveling Tip:
Many of the things you will want to see are ruins, and they are outside. Keep that in mind when you are planning what time of year to visit Rome. We visited at the very end of July, during a heat wave. Even with all the free fountains it was unbearable. There is no shade whatsoever at the Roman Forum.
Amalfi Coast
Top Sights:
Positano: This is a town that has gained notoriety in the last few years. Positano has a relaxed Italian vibe to it, and some of the most beautiful views. The drive to the Coast is itself a journey. Tight corners that cannot accommodate tour buses are plenty, as are barrierless stretches of road.
The town is filled with cute shops and beaches for swimming. Houses rise up with the mountains, right from the sea. It is very similar to Cinque Terre towns, except it is less busy.
Looking down at Positano
Amalfi: This town is the further of the two, and therefore, even less busy. While the scenery here is a bit different than in Positano (a town, backed by huge forested cliffs) it is still gorgeous.
One popular option is to take a boat cruise that hugs the coast of Amalfi. It provides a beautiful view of the town with its background, and offers an escape from the heat.
Amalfi on a busy Summer day
Where To Stay:
Unless you are adamant about staying in the towns, Naples is a perfect location. Each of these coastal towns are small, and therefore have limited accommodations. Even Airbnbs can be expensive in this area. We chose to stay at an Airbnb in Naples and take a small bus to the Amalfi Coast for the day.
Bay of Naples in the evening
First Trip To Italy Truthful Traveling Tip:
The Amalfi Coast roads are terrifying. With zigzags and long stretches of cliffs without barriers, it would make for a stressful drive. There are many small tours that will take you to the Coast for the day. If you are interested in staying longer, there is a shuttle service that will take you from the Naples airport or train station to your accommodations in Positano or Praiano.
Venice
Top Sights:
The Grand Canal: Venice is unique for many reasons, one of them being that it is a floating chain of islands. There are no cars, only footbridges, gondolas and water taxis. Spending time on the Grand Canal, the largest stretch of water in between the islands, is a must.
Whether you take a water taxi to dinner, or rent a ride on one of the infamous gondolas, you are in for a treat. Seeing Venice from the water is like seeing the city from a new set of eyes.
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Piazza San Marco: Basilica and Doge’s Palace: The most famous Square in the islands, Piazza San Marco is always, always busy. It provides a lookout to the water beyond the islands, as well as a home to Saint Mark’s Basilica and the Doge’s Palace.
The Doge’s Palace is unique to the islands. The Doges were the Venetian leaders, who made important city state matters. You can find one of the largest rooms in Europe here, as well as a prison for unruly citizens.
Exterior of Doge’s Palace
Where To Stay:
Staying on the islands gives you a totally different experience than just coming in for a day tour. We stayed at an Airbnb that was located on a narrow part of the canals, where we got to have the surreal experience of having boats and gondolas row past our windows.
The city is different during the day than it is early in the morning or late at night. Without all the extra tourists the city gets quiet. My favorite part of our time there was waking up early on a Sunday morning to empty streets and quiet canals.
The Grand Canal
First Trip To Italy Truthful Traveling Tip:
Although it is small, Venice is best seen over a few days. One thing we missed out on during our trip was a day trip to the Murano and Burano islands. Many tour companies provide day trips to these islands, where you can walk amongst colorful houses and visit a glass blowing factory.
Verona
Top Sights:
Juliet’s Balcony (Casi di Giulietta): This is one of the most iconic spots in Italy. Although Shakespeare based his tragic love story on fiction, this house has been declared the home of the Capulets, and therefore Juliet. You can stand on “her” famous balcony, and you can leave love letters all over the courtyard walls. The balcony oozes romance, and leaves you feeling very inspired in love.
The ugly? This place is insanely busy, and people do not mind the rules. Outside the tourist area, there is graffiti everywhere. The good thing is that despite the crowds and eyesores, romance supersedes the hassles.
While this is not Juliet’s balcony, it is a little less busy part of the museum!
Where To Stay:
Verona is probably the place where you will spend the least time, out of all destinations during your first time in Italy. You could easily see what there is to see in a simple afternoon stay. Therefore, it makes the most sense to stay in a bigger city. Both Milan and Venice are about an hour and a half away by train.
My dad walking through the streets
First Trip To Italy Truthful Traveling Tip:
There are soldiers armed with major weapons in major cities and near major attractions all over Italy. Although rare, if they approach you, follow their instructions. My dad and his friend were surrounded while drinking a beer at a cafe in Verona, and had their passports taken from them. They were told to stay quiet when they asked what the issue was, and 20 minutes later their passports were returned without explanation.
Milan
Top Sights:
Window Shopping: Like Madonna said, we are living in a material world. This is especially true in this city. Milan is a major fashion district with all high end boutiques. You truly feel like a kid in a candy store, even if you are only looking.
The Galleria Vittorio Emanuele II is the most famous of Milan’s shopping destinations. You can spend hours browsing through stores throughout the four stories of this building that was built in the late 1800’s.
Shopping around Milan
Duomo di Milano: A visit to Milan is incomplete without spending time at this famous church. It is located right across from the Galleria, and is easily recognized with its white, intricate facade.
You can spend hours just taking in the details of the exterior. Spending a dinner with the immense building illuminated in the background is the perfect way to truly appreciate the building. To gain access to the interior of the church, you must buy tickets. These can be reserved online to avoid waiting in line, and you have the option of paying extra for fast track tickets, to avoid long security lines.
The Duomo in Milan
Where To Stay:
This is a city in which you can immerse yourself in the life of luxury, by staying in one of the hotels right within the city. My dad stayed in Hotel Cristallo, a 3 star hotel located close to the train stations and bus terminals. With a full buffet breakfast, free WIFI, and a beautiful lobby it is the perfect place to stay comfortable in the city.
Relaxing in his favorite hotel lobby
First Trip To Italy Truthful Traveling Tip:
Keep safe when you are walking around the ritzy city of Milan. Everywhere you go there are warnings against pickpockets. Although this is prevalent in most European cities, you can imagine why the gains of pickpocketing may be higher in a city known for luxury shopping. Always keep your valuables close, and keep your eyes open.
Despite his serious face, my dad really enjoyed Monterosso!
No matter where you decide to go during your first time in Italy, you will have an amazing time. However, be warned that Italy has a certain beauty and charm, that will most definitely make you want to go back!
Enjoy Italy!
Samantha
& Danny (Cinque Terre, Pisa, Florence, Venice, Verona, Milan),
Two Truthful Travelers
I have always wanted to go to Italy and this list makes me want to go even more! Thank you for sharing!
Thank you for reading! Italy is a must-do trip!
Isn’t Italy just the best! I visited Venice, Rome, Naples and Perugia this year and really didn’t want to return home. Some of the best food and coffee in the world!
The food is definitely yummy; I’m not a coffee drinker so I can’t attest to that, but I have heard great things! What a nice trip you got to go on!
Nice great long post you have! I’ve been in Italy a few times but have not visited all these locations (yet!) Thanks for sharing!
Thank you!! I think it would be crazy to visit all of these places in one trip- I only made it to 5!
Thank you for this detailed post. It would be extremely useful when I plan my trip. Loved reading your tips and honest insights as well. It comes in handy when there’s so many options to decide from.
Thank you so much for your comment! I always like to include helpful tips that I wish I had read when I was looking for ideas when planning my vacations!
Italy is an amazing country. I think its very hard to go wrong with any city/town in Italy. Rome is incredible. I’ve been twice and lately I can’t seem to get it out of my head, so definitely looking at going again next year. And, the food!
I agree, I cannot imagine anyone finding a town or city that don’t like in Italy! Rome is amazing, there is so much to see that it is impossible to see it in just a couple of days. The food is sooooooooo good!
I love Italy its one of my favourite country’s in the world, in fact we’re getting married in Cinque Terre next Summer which is very exciting. Great to read your thoughts on Italy.
Wow, congratulations! That will be an absolutely beautiful wedding, with a beautiful backdrop!
It’s so sweet that you made this post with your dad! Were you the one that inspired him to start traveling later in life?
Thank you so much! I would like to think I have: since I started traveling he has been on a cross country road trip, a road trip to the Canadian Rockies with me and now to Italy. He traveled when he was younger but hadn’t in many years!
Such great places! I went to Cornwall in the UK this summer and a lot of those places look like a tropical version haha
Cornwall is so beautiful! I only got to spend one day there on my honeymoon, and the weather was dreary, but it is such a beautiful place!
Am so keen to visit Italy – your article just makes me want to go more. Thanks for the tips!
I hope you make it there soon, it really is a lovely country with so much history and variety!
Great list! I think if you managed to hit all these spots on your first trip you’d definitely be coming back for more! Verona is a favourite of mine. I still haven’t been to Cinque Terre but hopefully soon! I’m preparing for my third trip to Italy right now!
Amazing, I hope to go back some day! I wish I had more time to spend in some of the towns and cities, so I may even return to some of the exact same ones!!!
Ahh I want to go back to Italy so badly! We’re thinking of doing our honeymoon there, and I can’t wait. I went to Rome, Florence, and Venice in high school, and it was incredible
It’s an amazing place for a honeymoon! Especially Venice, where then you must go on a gondola ride!
What an incredible trip you had! Thanks for the first trip to Italy tips 🙂
Thank you for reading them! It really was a spectacular trip!
My husband really wants to go to Italy – and he’s Italian in heritage so he has distant family there. Looks like this was an amazing trip and you really got to see so much.
That would be an awesome trip for him then! There was a lot to see and do in such a short time, I just wish I had been able to stay longer!
These are very beautiful places in Italy, and you are so blessed to be able to travel around the country for your Honeymoon! What a great vacation it must have been for you two and your dad, too! I have been to a couple of the cities you mentioned with my family. We weren’t supposed to be able to see the Leaning Tower of Pisa, but because something on our tour got cancelled, they replaced that attraction with the Leaning Tower of Pisa! Pisa was well worth the visit!
That’s awesome! I personally haven’t been to the Leaning Tower but my dad said it was awesome! I had a very awesome honeymoon in Europe!
This is such an awesome in-depth look at Italy – definitely on my bucket list 🙂
Thanks so much! I hope you get a chance to see Italy soon, it has so many cool places!
This is such a great overview! I’ve visited Rome and Florence, but I really want to check out some other places and I just don’t know how to choose. So glad i read this!
Rome and Florence are a great start! It really is hard to choose, it was hard for me deciding where we would go and where we would save for next time!
I’ve never been to Italy but would love to visit one day!
Italy is beautiful! I hope you get a chance to visit soon!!!
These pictures and ideas are so spectacular. Bookmarking this for our trip… someday!!
Isabella x http://www.IsabellaDavid.com
That’s awesome, I hope it comes in handy when you are ready to travel to Italy!
What an amazing list! I went to Italy this summer and share some of your same favorites – others I’ll have to add to my list for next time! Italy’s such a dream <3
That’s awesome! Italy in the Summer is so beautiful, although according to my dad the Fall is much more quiet (and still warm!)
Sounds amazing! I am going to Italy next summer, I can’t wait!
Kasey Ma
thetsylewright.com
I hope you have a great time when you visit, there is so much to see!
I love Italy it is such a beautiful country. I plan on travelling there with my children next year 🙂
That will be a fun trip! I would love to go back and take my future kids to see the history and the beauty!
I love Italy! I’ve only been to 2 cities so far, and planning another one next year but I know that I’ll keep coming back to see the rest! Thanks for this helpful post!
There is so much to see! You could spend a lifetime visiting different places in Italy! Thanks for checking it out!
Wow! What a stunning trip! Italy is on my list of must sees!
It is perfect to be on a list of must-sees! There is so much variety in such a small place!
So lucky! I would love to visit Italy! It looks you had an amazing time, such a beautiful country!
I hope you get a chance to visit, and that your first trip to Italy is as amazing as mine was!
Your photos are all so beautiful! This is a great little guide for those planning a trip to Italy!
Thank you so much, I hope it is helpful to people taking their first trip to Italy!!!
Sounds like you had an epic trip! Verona is one place I haven’t yet visited, but definitely would like to.
I didn’t make it to Verona either, but I have heard it is quite the beautiful little town!
Oh I hope you had a blast! I just loved Italy!
I did!!! I hope you got to see some of the amazing places I did!
Wow, what a guide! Very detailed. I miss my times in Europe and I want to go back so badly!
xoxo Carolyn @ http://www.mychicobsession.com
Thanks so much!! Europe is a special place!
I love everything about this post! The images are amazing and your descriptions feel as if you have planned a trip for me. While I have no idea when I will make it ti Italy, I hope to someday.
Thank you so much! I hope when you visit you get to see some of these places in person!
I’ve been to Pisa, Florence and Rome but I’d love to visit the other cities you mentioned! Especially after seeing your photos.
Those are great cities! My favorite are the ones by the sea, although the historical cities are beautiful as well.
I love Italy SO much. The colors in your photos are stunning.
Thanks so much! It is a colorful country!
This post was very informative! Thank you so much for sharing! Looks like an amazing place to visit!!!
Thank you so much for reading! It is a beautiful place to visit!
I’ve only been to Rome out of these places, but I would love to go to all of them!
Rome is amazing! So much history that is still somehow standing!!!
I have always thought that Italy looks like such a beautiful place to travel. It looks like you had a wonderful time!! 🙂 Thank you for sharing your experiences there with everyone 🙂 I will definitely know where to look if I ever go there x
Thank you for reading, I hope that if you get a chance to visit this list helps you out!
Hey truthful traveller. You captured my experience of Italy fantastically. The total experience left an imprint on my mind and soul. It is so cool ? knowing we visit some of the same places with our own unique experiences. I need to return. The beauty and history was astounding and delicious.. Food was out of this world.. Thankyou for sharing.
Food was SO good!!! I am happy we could work on this together, and that you could add some cities to my list that I didn’t get a chance to visit!