Rome Italy

Italy: “DIY Itinerary And The Best Time To Visit The Country”

April 27, 2019
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Italy is one of the countries in Southern Europe that only in one small region can occupy you for a week as there are lots of things to see and do in this country. Your itinerary in visiting this country will be up to you on what’s important to you and what’s the main reason you do. However, I think most of the Filipinos or religious trips especially Catholic the highlights of visiting this country will be Rome.

I suggest visiting this country to allocate at least 14 days to be able to see most of the popular regions in the country. Travel experts in Italy suggest spending four days in Rome, three days in Florence, three days in Venice and four days in Milan would be an excellent itinerary to visit this country. If you have limited time slashed one day in every attraction or if you have less than a week I suggest to focus on the region that you like to see the most!

In planning a trip, I suggest to ask this following questions to yourself first, and it will help you narrow down the sites you will visit and help you with your itinerary.
  • What do you love to see first in this country?
  • What’s your biggest dream and what’s important to you why you come to visit this country?
  • Are you traveling solo, as a couple, or with small children, or with extended family? This one draws a big part of your decision too as it can affect how you move from one place to the other.
  • Everything starts with the question of what and why? If you are going to ask me this question my answer might differ to yours as our interests are different.
  • After we figured out the what and why? We will tackle the next one when the best time to visit this country?
  • One thing we have to consider is the weather as it can affect much to our packing preparation and our trip experience to the country we wanted to visit.
  • The last one but not least is to check the map of the country you can look at it by regions and cities then search for the attractions in certain areas.
  • The weather differs from North, Central, and South Region of the country but the best time to visit throughout the country with good weather is between May- October. 
  • Most of the major cities will be advisable to visit between April to June and or September to October.
  • Summer months are the highest seasons in Italy, but it can be searingly hot during this season. More people will be visiting the country plus the plane ticket is skyrocketed.
  • If you are in a tight budget the best time to save money in traveling to Italy is between March, April, and November. 

However, the weather in some areas in Italy can be cold and rainy during these months, but if you ask me, I would like to venture the end of April through the first week of  May and or end of May to the first week of June or first week of September and or October. If you noticed why I picked mostly the first week of each month, it’s because the first Sunday of the month in Italy they do offer free entrances to hundreds of museums, gardens, palaces, and state-owned attractions. Aside from this reason it mostly falls from our birthdays, and it will be memorable to visit during these months. My husband prefers to travel during cool weather where it won’t be too cold nor too hot. It will make sense for our family to pick these months to visit the country.

For you to understand the country, Italy is divided into two the South and the North.  The Northern cities are Venice, Milan, Florence, Cinque Terre, and the Leaning Tower of Pisa while the Southern cities are Naples, the Amalfi Coast, and Sicily.

Trrevi Fountain

Roma Termini

Thanks to the owner Jabilles family

Day 1

We will make a road trip going to JFK airport and ride a plane from JFK- ROM it will take at least 11 hrs total for the fastest flight. For the first day, I assumed we would arrive in the afternoon. So will go directly to our hotel to rest hopefully we will make it there before 5 pm so we can rest before heading to the evening of passeggiata (Rome’s quintessential see and be seen event at any day) to experience the stroll on Via del Corso from 5:00 pm – 7: 00 pm. From there we will head to eat dinner and stroll around the area.

Where to passeggiata in Rome?

  • Via del Corso (Tridente)
  • Campo de’ Fiori/Via dei Giubbonari (Lower Tiber Bend)
  • Piazza Navona/Via dei Cornari (Upper Tiber Bend)
  • Via Della Lungaretta/Piazza Santa Maria in Trastevere/Via Della Scala (Trastevere)
  • Via Cola di Rienzo (Prati)
  • Il Metro dell’Art
Day 2

We will wake up early in the morning and start our day at 7 am. I might get a tour group for Vatican Museum and Sistine Chapel, St. Peters Basilica aside from skipping the lines I wanted to see the Scavi di San Pietro Necropolis with St. Peter’s Red wall that is only accessible if you are with a professional tour guide. Then by noon we will head to the old city and enjoy the Tiber River and get some Gelato.

Day 3

I assume this will be on a first Sunday of the month and will attend a mass and head to Colosseum and Roman Forum will be the high lights of our day.


It will take 2 hrs, and 20 mins ride and the fastest train ride can be 1 hr and 7 minutes.

Day 4

We arrive in Naples and will visit the old city center Presepi Street to buy a figurine for nativity collection as we are Catholic so that it will be one of the highlights here then goes to the National Archaeological Museums and the Museum of Contemporary Art where they house some modern artifacts from other countries too. Strolling the historical sights and wandering around the area and see what other attractions we stumble as we try to navigate our way. At late afternoon, we will try to enjoy the views in the Park Of Virgiliano and St. Elmo.

  • We will surely find a pizza place as Naples is where the pizza is born and eat the famous dessert Sfogliatelle.
  • Entering the Museum Of Contemporary Art every Monday is free.
  • You might get in for free if you go St. Elmo an hour before closing.
Day 5

Planning to rent a car and wake up early in the morning head to the volcano of Mount Vesuvius and continue to visit Pompeii this will be a long day for us as we will try to keep our journey to the Amalfi Coast area.

  • If you have health problems, you might reconsider and cross out Mount Vesuvius and visit Herculaneum with Pompeii instead or just Pompeii.
  • There is a waterpark name Valle Dell’ Orso between Mount Vesuvius and Pompeii if you are traveling with children and wanted to do this instead of visiting archeological sights.
Day 6

Were already in Amalfi Coast area visiting some of the towns nearby and try to enjoy the beach of Sorrento, Positano, and or Maiori area.

Day 7

We make sure to slow down and enjoy the beach before heading back to the northern side of the country from Naples to Milan.


Trips will take 8 hours plus drive ( we might be sleeping on the train or bus for the night)

Day 8

We will arrive in Milan I assumed early morning would head to our hotel and left our bags in there check the places nearby and eat some breakfast will go to Piazza Del Duomo and check out Duomo di Milano the number one landmark in Milan that everyone doesn’t want to miss and the Duomo Terraces nearby. These two places will be the highlight of our trip, and it just depends on how the kids can manage to see more, but instead, I want to slow down and rest after the two and head to Navigli Canal during the afternoon to wander around the area, eat dinner and enjoy the night.

Day 9

There are two options to spend our days either go to Lake Cuomo less than an hour away from the main center of Milan or go to Lake Garda less than 2 hrs away. I would rather go to Lake Cuomo and not miss Bellagio wanting to check the souvenirs as it is one of the shopping areas of Milan not only for tourists but for locals as well. That will be the leading high lights of our second day to Milan, of course, there are many things to see and do the area, but I wanted to give some space for us to breathe and will go with where the wind will blow us while walking around the city.

Day 10

Our 3rd day in Milan will be happy to check out one of the shopping mall the Galleria Vittorio Emanuele II. Moreover, we will try to head to Piazza della Scala to see Teatro Alla Scala one of the famous Opera Theater in the world and will head down to Cenacolo Vinciano to see The Last Supper. The one mentioned above will be the highlights of our day before heading to Venice. In arriving in Venice, I expect to see the Grand Canal and enjoy the view it will be a rest day for us maybe we can rent a bike and drive around where the kids can enjoy.


It will take at least 2 hrs and 40 mins to hop between these two cities, and 2 hrs is the fastest, and there is 31 trips average per weekdays.

Day 11

Venice is a great city to explore, and some of the attractions are walkable from each other. Aside from seeing the Basilica di San Marco don’t forget to have a Gondola Ride and shopping for Venetian glass, it would be nice to have something that will remind you of the place you visited, and this one will be one of them. Other attractions to follow are Accademia Galleries, Doge’s Palace ( Palazzo Ducale), Piazza San Marco, Peggy Guggenheim, and Ca’ d’Oro.

Day 12

We will spend our morning in Venice before heading to Florence average travel time will be 2 hrs, and 2 mins and the fastest will be less than 2 hrs. The highlights of our trip will be the Uffizi Galleries as it is one of the landmarks in Florence will then try to walk our way to the adjacent side going to Piazza Della Signoria and Ponte Vecchio. If my little two chicks can make it through we will go to San Lorenzo Leather Market have a Tuscan Feast for dinner then find the best Gelato ( Vivoli ) in Florence.

Note: You can’t miss the Vivoli place as Italy is known for the best ice cream in the world and Florence is the one who has the best among them all.

Day 13

It will be our second day, in Florence and will be waking up early to see the Michaelangelo’s David Academia. Making our way to Brunelleschi’s Dome as I wanted our way up to the 463 plus steps to the top and if we can make it to the other one called Giotto Bell Tower total 414 steps to get the fantastic views of the city. The other attractions will be for consideration if time permits us to do so.

  • Those who have problems getting to the top you can opt-in going there as there are lots of things to see around the Duomo group that included to your ticket.
  • Other attractions are listed above if you want to insert one more here, Pitti Palace would be a great addition to your itinerary. You can rest under the shades, and if you have children, you can let them loose and not be bored with all the arts around Italy.
  • We will be heading back to Rome to make sure we can catch our flight on the next day assuming our trip will be early in the morning.
  • It takes at least 4 hours for slow travel from Florence to Rome and a 1. 5 hours for the fast train.
Day 14

It’s really up to our flight itinerary back home if it’s early in the morning on Day 14 or at night. Assuming our flight will be at night then we have one more day to spend around Rome.


You might be spending your night at the airport on Day 13 in Rome or spending another day in Rome.



Rome- 3 N/3D

Naples and Amalfi Coast area- 3N/4D

1 N- ( Will be sleeping in the train on the way to Milan for 8 hrs plus )

Milan- 2N/3D

Venice- 2N/2D ( will be spending total two days base on the time we arrive and leave)

Florence- 1N/2D

Rome- 1N/1D ( will be sleeping in Rome on the 13th Day and will be embarking on the 14 Day)

In knowing about Italy, it is such a beautiful country, and I entice anyone who visits here to make a way to Amalfi Coast to get a better sense of Italy knowing the people, culture, and traditions. Visiting this place just for 3-5 days isn’t enough to learn the country it is just for you to see some of the highlighted attractions. This Itinerary is customizable; it can be reduced based on your ability to walk around the city. For Florence and Venice, as many people visit this place for just a day trip, I suggest sleeping at least one night here for you to breathe a little and have a slight feel of the city and enjoy it.


Please count the number of nights that we are spending in each place, so it makes sense to you.


Airfare: $2, 000

Accommodation: $ 2, 000

Attractions: $ 1, 000

Food: $1, 000

Transportation: $1, 000


I’m hoping and giving this a budget of at least $ 7, 000 more or less for our family of four people. We belong to a middle-class family, and I always tend to book our accommodation based on its value.

Disclaimer: Please check the Tourism websites of Italy or directly contact them if you have any further questions all ideas are mine based on my research and how I want to see the country. You don’t have to follow the itinerary and or you can do your own based on your health requirement. The numbers are based on my observation on the months were planning to visit, and the days we will see the sights always know that in each country of origin and seasons prices can change drastically!

  1. Reply

    John Rieber

    May 1, 2019

    Just followed – love a great travel blog like this – bravo!

    • Reply


      May 1, 2019

      Thank you, John, for a great compliment! It’s good to hear from other writers too that is in the industry longer than I do.

  2. Reply


    May 1, 2019

    Perfect timing – I am getting on a plane tomorrow night bound for Naples! We will also be visiting Amalfi Coast, Rome, Florence, and Venice. Many of the sites you mentioned are on my list – but I think you have a couple more i did not know about. Thank you, perfect timing for reading this!!

    • Reply


      May 1, 2019

      I am glad you read this on time, and it’s nice to write and able to help with other travelers. Enjoy your trip!

  3. Reply


    May 3, 2019

    ahh gelato! doesn’t get better than in Italia.

    Joy at The Joyous Living

    p.s just subscribed to your blog 😀

    • Reply


      May 14, 2019

      Hi Joy, I just saw your comment! For some reason, WordPress will put some feedback to Trash glad I found it and restored just now! Thank you

  4. Reply

    Amanda | Toddling Traveler

    May 10, 2019

    This is a great itinerary, thanks for the detailed info! We visited Venice, Florence and Rome on our last trip to Italy and I’d love to see the Amalfi coast sometime!

    • Reply


      May 11, 2019

      Yay, how was it, Amanda? Which one is your favorite city among the three you visited? Yes, Amalfi is not to miss for in visiting Italy!

  5. Reply


    May 16, 2019

    This is so good, thank you for sharing the itinerary (i always want to go Italy) your post is helpful x
    thank you for sharing


    • Reply


      May 17, 2019

      You’re very welcome I’m glad to help!

  6. Reply

    Unwanted Life

    July 6, 2019

    Italy is a beautiful country with tonnes of history and historical sites to visit.

    Me and my partner did 3 days in Italy after spending 3 days in Switzerland.

    We visited Rome and Naples. We went to Naples to visit the catacombs, but the place is a little rough.

    Rome was great, but a few more days there would have allowed us to see more of such a great city. We went in May, because we wanted to avoid the summer heat there. Their was a heatwave that summer that year, so it was a great choice to go in the spring.

    A great post with some insightful comments about how to plan a trip there.

    • Reply


      July 6, 2019

      Thank you for taking the time to read and giving an insightful comments about Italy! I appreciate the feedback!

  7. Reply

    John Quinn

    July 6, 2019

    Wow that is one very full itinerary. Did you already make the trip and how did you do with fitting it all in? Italy is my favourite country bar none, I have had the pleasure of seeing some of these places. I do enjoy to hit the country a little more though. Great blog, and a very well put together plan.

    • Reply


      July 8, 2019

      Hello John,

      Not yet! Aiming to do it in 2021 it will be two years from now!

  8. Reply


    February 5, 2020

    I have always loved the thought of stepping foot into Italy. You guys must be good planners and I need to adopt some of the skills! I enjoy the breakdown of your 2 week trip 🙂 I tend to overspend when I travel, but you have given me information of what I should set my budget on!

    • Reply


      February 5, 2020

      Thank you, I am glad that I am able to help you with the planning.

    • Reply


      February 5, 2020

      I’m happy to help. Thank you for stopping by.

  9. Reply

    Jackie S.

    February 12, 2020

    Thank you for sharing this incredible Italy itinerary for 2 weeks. I have yet to visit Italy so this is helpful to know how many days to spend in each city and what to do there. It’s on my bucket list to try pizza from Naples and to visit Pompeii. Do you have a recommended pizza place in Naples?

    • Reply


      February 13, 2020

      I’ll reread the article and check because I thought I included it here. But I was able to read it during my research. I have never been there yet but this is the itinerary I made and came up with to follow on our journey. We planned to go next year but we will postpone it because we will be going home again in the Philippines. Our readers tend to look more articles about Cebu and the Philippines so I have to make more content that my readers trusted us to deliver. I’ll message you soon.

  10. Reply

    February 17, 2021

    Pretty fine post. I just stumbled upon your site and wanted to say that I have in reality enjoyed reading your website posts. Any way I’ll be subscribing to your feed and I hope you post again soon.

  11. Reply


    June 19, 2021

    Thanks a lot for writing this, it was quite helpful and showed me a ton


April Key Rode
New York, USA

April Key Rode is a Bachelor graduate of Hospitality and Tourism Management. One of the researchers in Tabuelan "As An Eco-Tourism Destination." She loves to do research, writing, cross-stitching and dancing. Her favorite sports are badminton, biking, soccer, basketball, and bowling. She is a mother of two, and she loves traveling with her own family and friends.

Rodes On The Road