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Travel Planning: 15 days in Italy

The planning of a trip to Italy

I have a travel planning guide that I follow regardless of the destination and time of stay. I decide the destination, buy the plane tickets (or other transportation), make some basic research about the place and book the hotel, basically that. But when the trip is longer, includes more than one destination and is international, it takes much more planning and organization. Read below how I planned a 15-days trip to Italy.


1. Basic research about the destination

Before the start of any trip, a long or short one, I always research (on blogs, tour guides, Tripadvisor, Yelp) about the place that I will visit. I look for what is most interesting to be seen and done, restaurants, nice bars, the best neighborhood to stay, and even local curiosities. I think this step is very important because it’s nice to have an idea of what you’ll find, and also because this research will serve as a basis to make some decisions, like the best place to stay and the possible itinerary options.

My research process is to put in a Word document everything that I find interesting, separated by topics (gastronomy, nightlife, museums, parks), I know it seems overwhelming, but this method helps me a lot. Of course, I don’t do everything that I write down, I only use the information as a guide, even because an over-planned trip might be stressful. Having a space for last minute changes is essential to enrich the experience.

Since this trip to Italy would be a little bit longer and we (two people) would visit several cities, the research was more intense and took more time to be done. Our plan was to travel by train, so we had to analyze the logistics.

For this trip, beyond the research, I made maps. I literally printed a map (so old school) and circled everything I had researched – even the train station and our hotel – this way I had a general sense of where I could go just walking, and all the attractions that were close to each other.

There is an easier way to do this; you just have to log in to Google Maps with a Google account and save the places that you want. Then you download the Google Maps App on your cell phone and log in; all the saved places will be there (the map works offline as well, you just have to download the area).

Check it out: I had a printed map with me and it was quite useful one time. When we got in Rome, our cell phones were not working, and we had to use the printed map to go to our hotel. Of course, we could’ve caught a cab, but we decided to save the money.

There are so many questions that appear when you start planning a trip: Where will I stay? If I arrive very late at the hotel, will I be able to check-in? Is this hotel close to the historic center or the nightlife area? Can I walk from the train station to the hotel? How long should I stay in each city? Should I buy a local cell phone chip, use a pay phone to call home or use the hotel’s wifi only? By the way, does the hotel has wifi? These details, if you don’t get informed before, can make your trip much less enjoyable.

To sum up, this basic research takes time before but can save your trip later. Details are important, remember that! And also, it’s cool to have an idea about the culture you are visiting, the basic habits. This way you are not going to make silly mistakes such as not paying adequately for the service in a restaurant, or use some piece of clothing that is inappropriate – nobody wants to be barred at the door of the Duomo in Florence, right?


2. Deciding the itinerary and the hotels

Before deciding the itinerary, you need to choose where you’ll arrive and from where you’ll leave Italy, for example, the journey starts in Milan and ends in Rome. Once you make that decision, you can set all the “middle” of the trip, the cities that you want to visit and how long you’ll stay in each one of them. Only after deciding the cities and the period of stay in each one, you can start booking the hotels. You won’t rent a hotel room without knowing the exact dates, right?

To travel in August we bought the round-trip tickets in April, and we booked all the hotels in the middle of June. We discussed what would be nice to visit in the cities that we were going to stay, and the cities close to them, to go and spend only the day. Our itinerary looked like this: Pavia, Ventimiglia (which was not in the plan), Milan, Verona, Venice, Florence, Pisa, San Gimignano, Rome and Sperlonga (also not in the plan).

After researching several hotels for a few days, we made our decisions based on the combo “value + location + quality of the breakfast + wifi”. All the hotels were satisfactory, some more than others, but overall we got them right. We slept in Pavia, Verona, Venice, Florence and Rome, the other places we visited we only spent the day or half day.


Use our search box to find the best hotels for you in Italy


3. Buying the train tickets

Train station in Milan

This part was a little stressful. With the itinerary decided and the hotels booked, we tried to buy the tickets all at once on the Trenitalia website (except the tickets of the one-day-trips), one month before the trip. I had read that the website was tricky to accept international cards, but I am a positive person, and I believed that everything would be fine, that all the mistakes that I know it happened to other people would not happen to me… Well, bad luck, they all happened!

I tried to use my card and others several times (you can not imagine how many), all international and unlocked, and none of them worked, I filled everything to receive in the end an error message. So I tried to pay with Paypal, and it worked at first. I was able to buy two tickets, but the third time, an error happened, and the website stopped accepting my Paypal. Then I created a new account on my brother’s name so I could buy the rest of the tickets, when I was buying the last one, the website also stopped accepting his Paypal. Two days later I tried again using my account and it worked. Hallelujah!

The Trenitalia website doesn’t require registration to buy tickets but requires a lot of patience. I think it’s really bad that it only gives you 9 minutes to complete the entire purchase, so if you want to buy all the tickets at once, you will not have enough time. Every time you add a new destination you have to put all the information again (because you don’t have a registration), which makes you lose a lot of time, so just buy the tickets separately.

We bought some Super Economy tickets, some 2 for 1 tickets, and some full price tickets because we bought only one month in advance (the sooner, the cheaper). When you finish the purchase you will receive a confirmation email with the ticket, you just have to print it out and take it with you on the train (or show on your cell phone screen), you don’t need to validate the tickets purchased online.


4. Budget planning

Receipts from restaurants in Italy

This part is complicated because each one has an opinion of what is cheap, reasonable, expensive and ridiculously expensive. In our case, we decided that we would spend a maximum of €700 per person in 15 days, with all meals, transportations, entrance to the attractions and souvenirs. In this amount is not included the hotels that we had already rented and the train tickets connecting one base city (I call base city all the cities where we rented hotels) to another. Well, the goal was successfully achieved, we spent less than the limit we set for ourselves, it was about €547 per person during the 15 days of the trip.

Traveling on a budget can be a bit stressful for some people, but you can have fun and enjoy the trip very well within the spending limit. You have to know how to dose and what is most important to you, visit all the churches? Go to all the museums? Eat in touristic restaurants? This answer depends on the type of program you enjoy doing; there is no right or wrong, just different types of travelers.

I advise you to take cash and card because some places that only accept cash and others only accept cards. Now you call me crazy and ask: “What you mean there are places that don’t accept cash?” Well, we went through a situation when we were trying to buy tickets in the Trenitalia machine, there was no place to put the cash, I am glad we had a card (international and unlocked) with us. I don’t venture to take only one way of payment when I travel; unforeseen happens and you’d better be ready. In this trip, we took cash, Visa Travel Money and international and unlocked credit card.


Summing Up

1. Decide the first and the last city of the itinerary

2. Buy the plane ticket to go and come back

3. Make a basic research about the destinations

4. Decide the rest of the itinerary (the middle of the trip)

5. Decide how long to stay in each city

6. Book the hotels

7. Buy the train tickets connecting one city to another


The prices presented here are from August of 2015 and the currency is Euro

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