How to plan a dream trip to Italy

I’ve been planning dream trips to Italy for a couple of decades, and have been getting paid to do it since 2008, when I started Italy Beyond the Obvious. I’ve personally created over 300 such trips, and I can tell you that the secret is in the planning. If you’d like to do it yourself, here’s how to plan a dream trip to Italy.

How to Plan a Dream trip to Italy

I’ve arrived at many a church, museum, and store to find it closed. I’ve tried to catch Sunday trains forgetting that they run differently or not at all on Sundays. I’ve shown up at markets at noon, just as they were being taken down. I’ve arrived at restaurants and art exhibits assuming I could get in, and discovered there were no available reservations.

It’s important not to be over-scheduled on vacation, but it’s equally important to spend time planning the things you definitely want to do. The way to accomplish this, for your dream trip to Italy, is to put on a project manager hat and spend time on the three areas described below. I’m convinced that travelers on a well-planned trip to Italy not only have a more relaxing and interesting vacation but also enjoy 20% more vacation time – time not spent problem-solving on the spot.

Italy Dream Trip

Photo by Voyages etc… via Flickr, licensed under CC BY 2.0


ONE Research itinerary activities that match your interests 

Guidebook Top 10 lists are a great starting point but it’s basically someone else’s list. Spend the time to create your own list.




TWO Rearrange the puzzle pieces until they fit

Look at your list, look at the calendar, and start putting the pieces in place. You’ll have a limited amount of time. You’ll have a longer list of things to do than time to do them, so it’s decision time. 



Dream trip Italy

“Yoga pose” by Syed Shameel via Flickr, licensed under Public Domain


THREE Visualize the flow

Before you book, but after you’ve arranged the pieces of your trip into something that you’re really excited about, sit back and visualize the flow of each day. Remember your personal travel pace and that you’re on vacation. Some tips:



Book it

You’re excited about the dream trip to Italy you’ve created: book it! Start with hotels, then work down your priority list, but book only what you need to book, so that you have some flexibility. If you’re going in high season or if you’re departing soon, you may need to reorganize details a couple more times due to availability.


How long does this take, anyway?

If you need to make time in your schedule for this project and want to create something as detailed and smooth as these sample itineraries, plan on spending about 6-8 hours per vacation day. If you speak Italian, you’ll save time in online research and booking, so knock off an hour or two.

And lastly, I’d love to hear how it goes! (really, I would. Please let me know.)

Photo of relaxing in Italy by db*photography; photo of zen by vramak

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