Toe to knee, the boot of Italy is a country chock full of amazing sites and flavors that make it one of the most requested tours we have! And for good reason, Italy does not disappoint. What we notice the most about travelers who want to take on the great italian adventure is that they want to do it all!!! And planning to do it all can be a really overwhelming task to take on. So, how to approach the great Italy Grand Tour? We’ve got a few ideas to get you started!
Cut Italy in half!
Draw an imaginary line between Florence and Rome. Then choose a side! Each side of the line has tons to do and can easily fill up two weeks. Imagine actually staying in Sicily for a few days then making your way to Rome through the Amalfi coast to round out you adventure in Rome via Pompeii? Now we’re talkin!
From the other direction, Picture yourself headed right into Milan for a quick two days before heading the the Cinque Terre, dipping down into the Italian playground of Tuscany with leaning towers, plenty of vineyards, amazing food and architecture. Now take a moment and continue that movie by rounding out your time in Venice. Yes!

Pick and choose among the “duplicate destinations”
One of the most frustrating things about planning in Italy is FOMO. And it’s real! But the truth of the matter is that while no two places are exactly alike there are a few they may do the same job. Take for example, Lago Como and Lago Lugano. Both beautiful, both the perfect three day getaway, both have great little towns dotting the coastline. Okay, one had George Clooney and the other doesn’t but there’s only so much A list celebrity to go around! Essentially, both do the same job. Trying to go to both may create a little overkill in your trip and that time may be allocated to something more essential. Here are a couple of other duplicate comparisons.
- Como and Lugano
- Cinque Terre and Amalfi coast
- Sienna and Assisi
- Pompeii and Ostia Antica
- Sorrento and Positano
- Verona, Vincenza, and Padua

3- Learn the train routes
By far, the biggest time waster in an Italy adventure is moving from one place to another. We highly suggest using good planning strategies like the hub and spoke method for day tripping or the directional advance for anchor cities. Both of those methods require a quick and efficient way to get from one place to another. Enter the massive, very well covered, train system. If you are planning anything from Naples north, knowing the train system is a must. And once you do, you’ll find that it is simple and fast! In fact, if you have round trip tickets out of Rome but you are ending your trip in Venice, we highly suggest taking the train back to FCO to SAVE YOU TIME over booking a hopper flight.
We know you saw it! We said Naples and north. Because for Naples and south, you’re going to have to do a little more digging as the train companies are not the same on all the tracks in this region. Start by learning the Train Italia routes then go from there. You won’t regret this decision.

4- Consider an agriturismo
Sometimes we focus so much on the bucket list experiences that we forget that rest is an important part of the travel equation. Italy has a particularly great getaway strategy in the form of the Italian version of the B and B: an agriturismo. Imagine yourself taking two days in the Tuscan countryside to stay on a vineyard laden farm and perhaps take a pasta making class from the host. Maybe you’d like to get involved in the olive picking process down in the orchard. An agriturismo could be just the thing that recharges your batteries midway through your trip while giving you a truly authentic experience. Win-win. Check out the official link for more.

5- Get your head around the art story
Okay, let’s chat. Americans, on the whole, are not good at understanding art. We just aren’t! It’s not your fault that, as a society, we are concerned with seeing the unclothed human form and don’t know how to connect to art. Check out our many podcasts and blogs about how to approach art and be prepared for the fact that a lot of it in Italy is naked. It helps to wrap your mind around a bit of the massive history so you have an idea of why some of these works are truly important. For example, why in the world are there so many Davids?! If you are really desperate to find an in with art try creating a scavenger hunt of the most famous pieces or choose an item like dogs or wine and see how many you can find in a given museum. There is a judgy cat in the Uffizi who will put up with you for a few minutes if you can locate him.

6- Create a list of what needs to be pre-booked
Here’s the deal. You are not going to get into the Colosseum without waiting in a line for a couple of hours if you don’t pre-book. It is what it is. For the life of me I d not understand that travel choice. Why in the world would you invest in travel only to stand in a line?! Just pre book and keep a schedule. If you’d rather not be so tied to the clock, we get it! Compromise and get tickets that are first group in the morning so you can enjoy and then keep the rest of the day free. While we are on the subject, please, please use official sites to book your tickets. Please do not give your hard earned travel dollars to any sort of third party! Here are just a few of the places that pre-booking makes all the difference:
- The Colosseum
- The Uffizi and Accademia
- The Borghese Gallery
- Anything that gets you to Capri
- St. Mark’s Basilica in Venice
- Anything dealing with the Vatican
7- Above all, plan like you will return!
We have so many clients who chat with us about their “once in a lifetime Italy plans”. Our question is what is preventing you from going back. The answer we usually get in response is something along the lines of “there are too many other places to visit!” If we could share one piece of advice about travel it would be that travel is not meant to be a quantity game, it’s meant to be a quality game. Italy is simply to big to take it in all at once! For that matter, Rome is too big as well. Imagine someone visiting the States and saying that they were going to do everything that was on offer here all at one time. An impossibility you say! The same is true of many destinations in Europe, and Italy is at the top of the list.
Our Take: 2 Weeks in Italy
- Fly in to FCO and take the train directly to Florence
- Spend three nights in Florence
- Spend three nights in Cinque Terre day tripping to Pisa and Lucca
- Take an agriturismo break for two nights
- Spend an overnight in a hillside town like Assisi or Sienna
- Head north through Milan to Lake Como for two nights
- Round out your trip with three nights in sublime Venice
- Depart from VCE
