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La Dolce Vita – The guide to planning your trip to Italy

Oh Italy, what a beautiful, special place.

The first time I went to Italy, nearly ten years ago, I knew that it would be the beginning of a long love story.

The easy atmosphere, the rolling sound of the language, the breathtaking views, the culture and history, and of course the simple and delicious Italian food – are all the reasons why I fell in love at first sight.

A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations


Ever since I tasted real Gelato for the very first time in Italy, a dream was born – to move to Italy, study professional gelato making, and live there for a few years {as evidence, I have a gelato tattooed on my right leg! ??}. Ok, so it hasn’t happened {yet!}, but even though I have visited many other places since then, Italy continues to maintain it position as one of my favorite destinations in the world.

The first time I went to Italy was on a family trip, and a few years later I returned for a girls’ trip with my mother, and this year I went with Daniel for an especially romantic trip. Italy continues to amaze and surprise me , taking another piece of my heart every time I go.

And still, Daniel and I were a little bit surprised {or even a bit frightened} by our Italian experience…

It’s not that Italy wasn’t a beautiful sight, nor were we disappointed by the food, rather we found a huge gap between what we expected Italy to look like in 2018 and what it looks like in reality.

And then we got it – we are so used to traveling to places that are caught up in contemporary culture and always trying to keep us with social networks, not missing the latest trends {for example, London and Krakow}, so much so that we were bothered by how different Italy seemed to us.

Italy does not give in to passing trends, it is classic and eternal.

And that is exactly what makes it so beautiful.

And why we fell in love, once again, with Italy.  



Before we get started, if you, too, dream of traveling to Italy, are planning a trip, or simply enjoy reading about the destination, I highly recommend that you download the Album ״Sings Italian Favorites״ and get into the magical Italian mood, or at least click ‘Play’ here :




If you’re planning a long trip to Italy, this post will help you get organized and plan the perfect trip to “the Boot”.

When is the best season to travel to Italy? What we included in our itinerary? How will you stay connected to the internet during the trip? What should you know about car rental and public transportation? What is the difference between an ‘Aperitivo’ and a ‘Riposo’? For all the answers,  and more, read on…

{P.S. – Have you signed up for my FREE traveling course to help you plan your future vacations “like a pro”?}



A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations

A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations

A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations




Italy is a place that is fun to visit throughout the year. The summer is {usually} not extremely hot, the winter is relatively comfortable in comparison to other European destinations, and the in between seasons are nice with a slight chance of rain. If you’re busy wondering when is the best time to go to Italy –   I’ve created a short and useful list according to the seasons:

Summer –  From June to September. Summer in Italy is hot and humid, especially in the south of the country, which is why it is the ideal season to visit Italy’s beautiful beaches, or alternatively, to spend time in the northern  part of the country, where it is nice in the summertime. Keep in mind that despite the heat, swarms of tourists make their way to the big cities at this time of year making the prices high and the sites packed. {I personally experienced this in Rome during the end of the summer, and it was not the nicest experience ?}.

Fall – From October to November.  This is the season in which the temperatures drop, along with the prices and the amount of tourist, and Italy is painted in the beautiful fall color palette. The weather will be mostly promising, comfortable, but the days do begin to get shorter and there is a slight chance for rain every once in a while.

Winter – From December to March. This is the ideal season for sport lovers to travel to Italy’s mountains. If you’re into wintery vacations, the kind that include sitting inside coffee shops, visiting museums and going shopping, Italy’s big cities will be a perfect place for you to spend your winter holiday.

Spring – From April to May. The temperatures begin to rise, the flowers are in bloom, and it’s the ideal time for nature hikes and vineyards. Keep in mind a slight chance of rain.


A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations



One of the best tips I can offer you about traveling in Italy is to book tickets in advance! We got ‘skip-the-line' tickets for all of the attractions we experienced on the trip, and skipped the entrance line completely. Using ‘Skip the Line’ tickets is so easy, after booking, you receive a PDF file to your email, which you then show via smartphone at the entrance to the attraction. If you’d rather take the chance and not order a ticket in advance, to avoid having to stand in line you should be there before opening time. {But honestly, save yourself the headache and just use use ‘Skip the Line’ tickets. Super convenient!}.



A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations






Our dreamy trip in Italy lasted a little over three weeks {Sept 16 – Oct 4}, during which we spent most of our time in the center of of the country, the Italian Riviera, and a tiny part in the northern part of the country.

We divided the days of our as follows:

✴  4 nights in Rome

✴  4 nights in Tuscany

✴  2 nights in Florence

✴  3 nights in Spezia {Cinque Terre}

✴  2 nights in Milan

✴  3 nights in Venice


A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations

A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations

A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations


Even if you haven’t prepared a long to-do list of all it is that you’d like to see and do, an urban trip can be very exhausting as you will probably spend most of your days on your feet. Last year, when Daniel and I went on our first urban trip to the amazing Japan, we decided to combine two short vacays into one energy-boosting trip. It was without a doubt one of the best choices we have ever made, allowing us the much needed rest and to carry on with fresh strength. That is why we decided to make the same concept “a vacation within a vacation” a new tradition, and this time around we booked two extra special separate holidays. The first, at the Castel Monastero Resort & Spa in Tuscany, where we enjoyed a fun and relaxing pool-day under the Tuscan sun, as well as a pampering spa and excellent meals. The second was at San Clemente Palace Kempinski in Venice, to complete the trip with an extra sweet flavour.

A little tip – If you are planning a long trip, do yourself a favor and treat yourself to a little vacay within your holiday ?

And one more tip for the road, about sleeping arrangements in the big cities – when it comes to this kind of urban traveling, the kind that eats up your day from morning to night, it is best, in my opinion, to give up the hotel room and go for an AirBnb apartment. {Check out the apartments we chose in Rome, Florence, La Spezia and Milan}. You probably won’t have enough time to enjoy the hotel’s facilities, so best to save the money and spend it on something else {for example the hotel  you will treat yourself to from the last tip ?}.

First time booking an apartment through AirBnb website? Feel free to use my link and receive a coupon code for $41 on your next trip.


A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations




The truth is, internet in Italy is pretty simple to connect to. In every hotel and apartment we stayed at, we had excellent wireless connection. There are also a few free Wifi hot spots around the country which can be helpful at times, but most of the time aren’t ideal because too many users slow down the connection. If you plan to use the internet outside of your hotel or apartment for apps like Google, Waze, WhatsApp, social networks etc, I recommend purchasing a local sim card as soon as your arrive in Italy.

We bought ours from Vodafone, the company has branches scattered all over the country. The price of a sim card in Italy is divided into two – the cost for the card itself is 15 euros and the 8GB charge for surfing the internet {together with a small airtime package for use inside Italy} is an additional 10 euros. In case you use up your package and would like to load your card with extra data, you will be asked to pay only for the data, and won’t have to pay again for the card {although 8GB should be enough for your trip}. The sim card will be activated immediately, at the point of purchase. All in all, it is a very simple process.






Car – As our trip included visits to Tuscany’s towns and villages, renting a car seemed like a most necessary choice, and added a lot to our trip too. With that being said, if you’re not planning to leave the major cities, there is no reason for you to rent a car in Italy. {Getting around the country can be done by trains, but I’ll get to that soon}. If you’re traveling through Tuscany, or other areas that are more easily accessed with a car, don't think twice! Renting a car in Italy is simple and inexpensive 🙂

Here are some things you should know before doing so:

✴ Don’t give up on comprehensive insurance , and make sure you understand what it includes at the time of booking. Most of the time, when renting a car, the rental company will try and sell you “upgrades” which you surely will not need, so it is important that you know ahead of time what the insurance includes, and what exactly you do and don’t need.

✴ Use Waze as your navigation system, because the roads can get pretty confusing. {Don’t forget to charge your phone in the car because the app tends to eat up your battery life ?}.

✴ Keep your eye on the speedometer {Waze can help you out!}. Although I’ve read that traffic laws in Italy are rarely enforced, but when they are, the fines are quite high.

✴ Be aware of Tolls. It will cost you a bit more, but will save you a lot of time.

✴ Use the ‘self-service’ stands at gas stations to save a buck.

✴ The small Italian towns are not the most car-friendly {especially if you’re not used to driving through small alleys}, so your best option would be to try and look for a parking spot in one of the lots at the entrance to the town or village.


A Guide For Planning A Trip To Italy - plan your trip like a pro with my tips for the top destinations


Getting Around on Intercity Trains – It is very convenient to travel through Italy by train, but since we used the car from the moment we left Rome until we reached Milan, only when we left Milan for Venice did we get the chance to use the train. If you plan to do Italy by train, you should peek at this article about trains in Italy, it makes everything clear.


Trains and city buses – To tell you the truth, we did most of our wandering around the city by foot {and good thing we did, given the amount of carbs and fats we consumed on this trip ?}, while in Rome and Milan we used of the public transport to reach places that were a bit further from the city center. Generally speaking, I always prefer to use Google Maps to help me navigate and find the best possible route to get from place to place.

Rome – the metro in Rome has only three lines that reach all the main attractions in the city {the Colosseum, the Vatican, Trevi Fountain, the Spanish Steps, Vila Borghese}. From what I’ve read, during rush hour and on the weekends, the metro is extremely crowded to a point that it is difficult to step into. So we chose to skip the metro and took the bus and tram instead. In the city, a ticket for the bus, metro and tram cost 1.50 Euro and lasts for 75 minutes. You can also buy a daily pass for all public transportation {metro, bus, and suburban} which costs 7 Euros for 24 hours. The ticket can be purchased at metro stations, tourist information kiosks and newspaper stands.

Milan – while the buses in Milan are terribly crowded, so much so that we avoided getting on them, the metro is very convenient. The cost of one train ride is 1.50 Euro and the ticket lasts for 90 minutes from the time you use it to enter the station. If you plan on doing more than two rides in a day, you’re better off buying a daily pass for all public transportation {metro, bus, suburban}, it costs only 4.50 Euro for 24 hours. Both types of tickets can be purchased via machines in found in the metro stations.


It is important to make sure to validate your ticket in the right machine to avoid being fined.



Taxis – Since most of Italy's urban attractions are concentrated in one area, or close to major public transport stations, we hardly ever took taxis in the cities on our trip. In Italy, you can get into a taxi or an Uber, but from my little bit of research, in this case the taxis are actually cheaper. We took a taxi only a few times when we were moving with our suitcases from place to place, and although it isn’t the least expensive option, it is without a doubt the most comfortable. If you’d like to use an app to order a taxi, you should download MyTaxi, an app that works in English and is very easy to use.



The best coffee in the world  You can’t discuss Italy without mentioning the divine coffee that can be found at any time, any place. Every morning of our trip, Daniel and I would start the day with a perfect espresso or macchiato, taking it usually in one shot at the bar, just like the locals do. At first this Italian custom, of drinking coffee and eating a pastry while standing at the bar, seemed strange to me, but once we tried it, we totally understood its charm! By the way, in Italy, drinking at the bar will cost you around one or two Euros, a lot less than sitting which could cost double or even triple.



The Italians take their Riposo very seriously  The Riposo is the Italian version of the Spanish Siesta. The Italians traditionally take a lunch break that lasts between an hour and a half to two hours {1:30 – 4:00pm} to go home, enjoy a long lunch, and relax with their family before returning back to work in the afternoon. This is why many shops and restaurants are closed at this time of day. Of course I don’t mean the major chains, open all day, rather I’m talking about the small, local businesses. It’s best to check Google for opening hours if there is someplace you would hate to miss.

Aperitif Culture  If you ask me what I enjoyed most on our trip, you may be surprised that my answer is not pizza, pasta and gelato. Don’t get me wrong, I came back from Italy with a serious addiction to carbs after eating the above short list at least once a day while we traveled. But my favorite word, and custom, in Italy is the Aperitivo! The Aperitivo is the Italian happy-hour, and is available at restaurants and bars between 6-9pm {usually lasts two hours, times vary from place to place}. The Aperitivo – a cocktail and snacks – is meant to build up your appetite before dinner, while hanging with friends after a work. The snacks are usually very good – and are  served either on a plate or a small platter with a few options, or an all-you-can-eat buffet.



Dinner is served quite late in Italy,  a direct result of the previous paragraph, most restaurant open for dinner after 7pm. Don’t worry, the Aperitivo snacks will keep you from arriving too hungry at the dinner table. Generally speaking, I don’t think it’s possible to be hungry when traveling through Italy 🙂

Tipping at Restaurants  In Italy, it is not customary to leave a tip in restaurants and bars. Many places have what’s called “coperto” which is an additional charge of 1-3 Euros for the service, and acts as the tip. If you see the word “coperto” or “Servizio” printed on the menu you’ll know that the additional cost will be added to your bill at the end of the meal. From what I’ve read, if there is no service mentioned on the bill, it is customary to leave a tip that consists of 1 Euro per customer, or that amount rounded up.  By the way, sometimes bread appears as an additional cost on the bill , even if you did not request bread when you ordered {you will see it on the bill as pane}.

Gelato  The real Italian ice cream, made of the best ingredients, with a perfectly creamy texture and concentrated flavors,  you will probably eat at least once a day during your trip. Although all ice cream shops in Italy are known as “Gelato”, they are not necessarily all that good… Rule of thumb to avoid bad gelato is to stay clear from those presented in the freezer as tall ice cream “mountains” – the good kind won’t be piled up like that, and even better is if each flavor is covered with a metal cover!



The pizza battle  No, it’s not what you think, my battle with pizza was not how to find ways to eat less of it – on the contrary – to eat as much of it as I can! So why a battle? Because, for some reason, in Italy they tend to serve the pizza without slicing it, and sometimes, the knife you get is not exactly up for the job. Anyway, I don’t like to waste my time slicing pizzas {and to be honest – I’m really not that good at it!} so it’s too bad I only realized I could ask them to slice it for me when I was eating my very last pizza of the trip. If you, like me, prefer your pizza to arrive sliced, don’t hesitate to request the service from your waiter.

For salad lovers  unlike many places around the world, in restaurants in Italy you can actually find salads that consist of more than just lettuce leaves.  But, and this is a big but, for some reason they don’t season the salad before serving it! At all! I get it, there is olive oil and balsamic vinegar on the table, but when I order a salad I expect it to be ready, and by that ladies,  I mean a seasoned salad. So, if ordering a salad, don’t be surprised if it shows up a bit dry and sad looking, give it life with the tasty Italian olive oil and balsamic vinegar ?


I hope this guide helps you out before your trip to Italy ?
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6 Responses

  1. awesome post
    italy is wonderful for traveling. it was a good experience to travel with Italy guides thanks for sharing the beautiful pictures.

  2. Hi there!
    I really really like your page and I love your photo’s! They are beautiful! May I ask which filter/app you use?

    1. Thanks darling!
      I’m editing all of my photos with a costume made preset {fulter} I’ve created on Lightroom.
      I’m working on an online photography & editing e-course, be sure to sign up to my newsletter if you’re interested to know more!


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