Italy has everything.
It has the sea and the mountains, the hills and the plain. It has lakes and rivers and forests and national parks. It has incredible ancient borghi and larger cities that have managed to enter the modern age with a firm hold on their ancient pasts. It has Medieval castles, Renaissance art and even contemporary art scenes.
Here you can shop your day away, searching for whatever you need at whatever budget, from flea market finds to Montenapoleone. Visitors come for the breathtaking views and food so good that you might be tempted to unbutton your pants and dive back in, ancient Roman style.
The downside, is that Italy has everything. It feels nearly impossible to decide what to see, how to see it and what to give up this time around. It’s easy to be overwhelmed when you have so many options!
So let me help you. Plan your Italy trip step-by-step and you’re sure to find something that works for you: A trip that combines your time, money, must-sees and must-dos (or eats!) all in a wonderful Italian vacation.
Because there’s plenty to consider even before you get to the Bel Paese:
Fix your time, budget and season
Which of the three takes precedence is personal, but one will most certainly influence the others. Only have seven days off work? There you go. On a tight budget? That definitely needs to be taken into consideration before throwing yourself in the deep end of Italian cities and sights. Our time and budget is dependent on many things and completely variable, but you need to have it down before planning your trip, or you risk doing all the research and planning and having to throw it all away when you realize it doesn’t fit in the time or you don’t have the money. Le Marche is a particularly budget-friendly region, but even Milan can be done one a budget when you know ahead of time!
Also, now is when you need to decide when it is your able to visit. Italy is gorgeous year-round and has something special to offer for each season, but it might influence your itinerary later on. For example, coming in August but hate crowds? You better avoid the big cities then! Coming in winter looking for warmth? Best to head south.
Compare your options with Winter in Italy and Italy in August: What to Expect
Plan your itinerary, DON’T overdo it
Let me be direct: y’all are trying to see too much. Yeah ok, it’s possible to see 14 cities in as many days, but you won’t see much. I know how hard it can be. You’ve saved up time and money and you want to get your worth, but trust the universe that jam-packing your trip will only ensure that you are constantly moving, never resting and never having the time to see a destination well.
So, make a decision. Most first-timers to Italy hit the major sites: Rome, Florence and Venice. All well-connected by fast-train, it’s an easy itinerary. Then decide how to divide that trip based on the time you have. If you only have a week, no adding on side trips! Other options include choosing a specific region to tour, making a base and taking side-trips, small-town touring or whatever destinations you have in mind, just choose a reasonable amount of destinations within a reasonable time-frame.
Check out your flights
Unless money isn’t a problem, flights into Italy can determine a large part of your Italy travel. Usually flights from America fly into Rome or Milan while secondary airports like Venice and Naples tend to cost a bit more. Where you fly into determines the order of your itinerary and maybe even what you see on this trip.
Keep in mind also that open-jaw flights, those that fly into one airport and out another, can be more convenient for some itineraries but also tend to be more expensive.
Plan your itinerary geographically
I’ll never understand those who already know the destinations they want to see but don’t know what order to see them in. Your goal here is to waste as little time as possible, so plan your itinerary in geographical order. Consider also high-speed train times versus regional and where you’re flying out of, but otherwise just look at a map.
Then, once you have your order, consider planning a flexible day-to-day. Even the most freehearted, spontaneous traveler will benefit from a daily itinerary. You don’t need to follow rigidly follow it, but a clear itinerary will help you to not waste time and easily visit your must-sees. Make a list of the top sights that are all near to each other. Then when you head to a particular part of the city you can see them all, rather than ping-ponging across town wasting time and energy.
Weigh your transportation options
Your transportation choice depends on where you want to go. If you’re sticking to the big cities, ditch the rental car. If you want to tour the small towns or a large region, consider it. If you’re doing a mix, check out both. For example, if you’re based in Florence you can tour the city, then easily take a train to major Tuscan towns like Siena, Lucca, Viareggio and Pisa. If you want to get to even smaller towns you’ll have to take the bus or, for more freedom, get a car.
Italy has great public transportation options for tourists (commuters might say otherwise) and train is often the most convenient form of transportation between Italy’s major cities. That said, it’s hardly worth it if you’re trying to stop in Perugia for one day then Cortona then any other tiny town in Umbria or Tuscany or anywhere.
The easiest way to weigh your options is with Rome2Rio, a website that will show you all available forms of transport from one destination to another as well as time, cost and distance. Find more resources at my Italy resources page.
Book your tours or entrances
This is best done before getting to Italy as well. Day tours are often sold out months in advance. Don’t even think about seeing the Last Supper if you haven’t secured your tickets a half a year before your desired date and expect to wait in a line for hours at the Vatican Museums if you don’t already have a ticket. Not only that, but by booking a couple days before we were able to enjoy a night tour of the Colosseum for 20 euro each, a unique experience we wouldn’t otherwise have been able to enjoy. Big-city tourist-site Italy is not for the spontaneous traveler, so if those destinations are on your must-see list, plan ahead to not miss out.
Research the sites!
You’ve likely already done this while deciding on your destinations and itinerary, but now that it’s all finalized, it’s time to research in earnest. Read up on the culture, the social norms and the history of the places you’ll be visiting. The forum in Rome is just a pile of rocks for those who don’t know the history (or aren’t on a tour). Those who do will see the remains of an incredible empire. The Verona Arena is a pretty theater on first sight, but when you know that it’s actually 2,000 years old and has been at one time or another a theater, apartment building, brothel and shopping mall, you might see it in a new light.