Have you got your trip to Italy booked? Congratulations! You’re about to embark on one of the most magical, cultural, and beautiful trips of your life. My trip to Italy truly changed the world for me, and no doubt you are so excited for an experience that will change your world, too! So now that you’re booked up, what’s next? How do you get ready for this amazing trip?
First thing is first, get planning!
You may be thinking, but wait? I thought I already had a plan? Yes, you have a main plan of where you’re going and when, but that’s it. What about what you want to do there? Don’t waste precious time, and get started on setting up important activities on the things you know you must see and do, right away. Italy is a very popular destination (especially in the summer) and if you don’t act quickly you could miss out on booking some of the most incredible must see and do experiences, or way overpay on pulling them together last minute. Tours can book up quickly, especially private tours, so as soon as you have your dates, get to work on your planning and don’t stop until you’re satisfied that you’re ready.
How can I plan for these must see and do experiences?
Start out really simply. Make a list of the hotels and/or cruise ships you are going to be in, with the dates so you get your main broad itinerary. I say broad because, if you’re staying a hotel in say, Rome for example, you have access in a few hours or less train ride to about half of Italy, so just because you may be staying in Rome doesn’t necessarily mean you will be in Rome all those days, in fact day trips are not only really easy, but they are promoted throughout Italy. If you haven’t thought about leaving the city you’re staying in for a close by day trip, open up a map and check out the surrounding areas. You may be really surprised at how accessible another part of Italy is that you’re interested in but cut out of the trip when making your booking.
A simple broad itinerary will look something like this:
Plan for the unexpected!
One of the best tips I can give you when making your plans is DO NOT, and I repeat, DO NOT, fill up everyday, and especially not every second of everyday of your whole trip. It’s a vacation, not a marathon. The whole point is to enjoy it, and while some hyper-organized people will be super inclined to plan out every moment wanting to maximize their time abroad, let me tell you in advance, this is sheer folly. Make flexible plans as much as you can, and only have set plans for your absolute musts. The fact is, it’s the unplanned experiences that will be some of the best if not the best memories you have from your trip. You also don’t want to exhaust yourself to the point that you are not enjoying the trip or able to have any fun, or even worse get yourself sick from pushing yourself way too much to pack in way too many things.
When in Rome, do as the Romans do
The phrase ‘When in Rome, Do as the Romans Do’ means to follow the traditions or customs of a place being visited. It refers to the importance of adapting yourself to the customs of the people who are in a certain place or situation and behave like they do. While in Italy, one of the most important ways to immerse yourself in Italian culture is to apply the southern Italian philosophy of Dolce Far Niente, that is, The Sweetness of Doing Nothing. Make plans to not have plans. Wander around, talk to the locals, try the food, drink the wine, just be, and you will enrich your trip in ways you never would have imagined.
Now I don’t know how to proceed, do I plan or not?
Like I said before, definitely make plans, and this is the easiest and simplest way to do it. After you have your main broad itinerary make a few other simple lists:
- List 1 – Your absolute musts for each location. For example, if when in Rome you will just die if you don’t tour the Colosseum, sit on the Spanish Steps, spend a night at the Trevi fountain, or whatever it is that gets you pumped up about seeing Rome, make a list of those things. Need ideas? Check out my things to do in Rome post.
- List 2 – Your interests. Do you like museums? Artwork? Gardens? History? High Tea? Spas? Architecture? Shopping? Walking tours? Ruins? Cooking classes? Trying different drinks in bars? Are you a foodie? Make little lists of the top places to go get your groove on for each of your top interests for each location you will be in, even if only for 1 day. Then as you have time during your trip and aren’t sure what to do, you will already have little lists made up of where to go and what to do, the point is that it’s flexible, so you can fit these things in as you find the available time to do them.
- List 3 – Optionally, make a list of the previously mentioned day trip options that interest you. For example when in Rome you can day trip to places like Florence, or other parts of Tuscany, Naples and the Amalfi Coast, Cinque Terre and those are only a few. Make a list of your interests and then as you finalize your plans you will be able to make the call on any of these you want to commit to doing for sure, or you can plan to book them as you find the time once you are there, but you’ll already know what’s possible. Need help? Check out my day trips post.
I have all the lists, now what?
Now is the crucial part. Decision time.
- Take a look at your lists and prioritize what you for sure want to do, no matter what, in each location.
- Figure out how you want to do it. Do you want to do a tour? Will you have a guide or do you want a guide? Is it an activity that needs to be booked with a company? Do you need a car or other transportation to get there?
- Book it.
- Anything booked you need to add it to your broad itinerary list, as it is now part of your set itinerary.
- Repeat until you have set into place the things you absolutely must do no matter what, and leave the rest of your time up to your whims, but don’t worry, you still have your interests lists to check on the trip of where to go and what to do when you have time.
A few extra tips, with love:
Plan downtime when you first arrive at each location. Traveling is tiresome and exhausting especially long international flights, but even the high speed trains for hours will tire you out. You will need some rest upon arrival anywhere so either book nothing on the travel days, or book something really lowkey like a private tour with a driver that will do what you want them to do not dictate to you what to do, or something like a spa treatment to revive you. Nothing with tons of walking should be planned on a travel day as there will be a great deal of walking with luggage, on cobblestones, and confusion, and all the other stress on travel days where you’re going through airports, train stations, and etc. You really don’t need to add onto that and get fatigued. Nobody wants to be dragging their feet around forced to do tours when they’re dead tired.
Always have an escape plan if you get dead tired so you don’t get stuck miserable somewhere. Free Now is a great app to have on your smartphone that works like Uber/Lyft, but for Taxis. There are networks of private drivers you can connect with via WhatsApp. This is especially essential if you are traveling with someone with limited mobility, elderly, or young.
Upon arrival at a new location a simple guided tour to give you an overview of the city/area is a good idea. For example the golf cart tours in Rome are an excellent and easy way to see all the highlights of the city. After a tour like that you’ll have a good idea of your further interests and making future decisions on how to spend your time will be easier and more fun.
Have a question? Let me know and I’ll do my best to help.

