February 17


How To Plan A Trip To Italy – FCI 040

By Rick

February 17, 2020

On the podcast today, I talked with my friend Victoria De Maio about how to plan a trip to Italy. We discuss four general types of travel: Large Groups, Small Groups, Custom Tours, and “Do It Yourself,” and we compare the pros and cons of each. 

Afterwards, I reflected on my very first vacation to Italy in 1999 (bring back the Lira, per favore!), which wound up being a combination of these types. For part of the trip, I had tagged along with a large group that was hosted by a friend of mine. I can’t remember exactly how many were on the tour, but I seem to recall three massive tour buses. So yeah, Large with a capital “L.” 

But then I stayed in Italy by myself for another week after the tour ended, and I had enlisted the help of an old-school travel agent to help prepare the itinerary; in other words, “a custom tour.”

The DIY part of it was that I had found my own accommodations in Spello based solely on an article I had read in Travel+Leisure, or one of those other fancy/glossy print magazines that are quickly becoming extinct. 

Victoria De Maio in Puglia

Victoria De Maio and friends, toasting to La Dolce Vita in Puglia

Well, that’s what you did in the good ol’ days before the glut of (mis)information on the Internet. I devoured travel magazines and waited impatiently for the New York Times travel section every Sunday. But it must be said that the information wasn’t always up to date by the time it went to print, so that particular portion of the trip was not without some misadventure, as I chronicled in an earlier blog post about “The Best Way to Learn Italian.” (Hint: FULL and unintentional immersion!)

OK, enough backstory. Let’s break it down by exploring the pros and cons of each type of vacation.

How To Plan A Trip To Italy, 4 Options:

Large Group


  • Generally cheaper
  • Meet lots of people
  • See a large number of "checklist" sites
  • Wide choice of destinations


  • Overly-ambitious itineraries
  • Time spent waiting on others
  • Large chain hotels
  • Tourist restaurants


This type of tour might be the right choice for the first time traveler, especially if you're traveling alone, and want to get lots of selfies in front of the greatest possible number of famous monuments. Usually cheaper, too. 

Small Group


  • An intimate group, with easy access to tour leader
  • Boutique hotels
  • Family-run restaurants
  • Unique experiences (ex. cooking class)


  • A bit more expensive than large groups
  • Some free time, but also some scheduled events


When done right, this type of tour combines the best of all worlds. The itinerary will make sure that you see the best sites of a region, while allowing you enough free time to feel like you're actually on vacation instead of a scavenger hunt. Small groups allow for quaint hotels, authentic restaurants, easy passage on the roads (as opposed to tour buses), and access to unique experiences not possible for larger groups. You also can have conversations with the tour leader instead of being shouted at via megaphone. At the same time, the price will be less than a custom tour.

Custom Tour


  • A personalized itinerary
  • More freedom of your time
  • Ultra-specialized experiences


  • Usually more expensive
  • A bit isolated within only your group; no new friends


If you've been to Italy several times and you know exactly what you want to do, see, and eat, then this might be the right option. For example, if you've Rome, Florence, and Venice, and now want a week touring the wineries in the Tuscan countryside, a custom tour planner will make sure that your dream matches the reality of your trip.



  • The “fun” of mapping out your trip
  • All the flexibility that you'd want on the ground in Italy


  • Reliance on “crowd-sourced” information
  • Very easy to make big mistakes that could ruin your vacation


With all of the tools online these days, there is no reason why anybody couldn't plan their own trip to Italy. However, just because you can doesn't mean that you should. There are so many different ways that things could go terribly wrong. That said, if you've been to Italy several times and only want to go to Rome and Florence, for example, you should be able to pull it off without too much risk. 

Victoria and friends enjoying Cinque Terre

Victoria De Maio 

Victoria De Maio has been traveling to Italy for years and, not only does she love traveling to Bella Italia, exploring her beautiful cities, towns and regions but, she also loves helping others plan their “la dolce vita” vacation.

Further, she has enjoyed many cooking classes, olive oil and cheese tastings, wine tastings (of course!), guided walks, and artisan visits. So not just the "tourist" itineraries, but also the immersive experiences.

Always amazed by so many phenomenal museums, cathedrals, and ancient ruins, the more she sees and experiences, the more she wants to see and experience. And, the more she wants to share with guests. She wants them to experience the Italy that she loves!

In addition to tours, she loves working with clients to create exactly what they want to do on their trip to Italy and when they can and want to travel! (Especially for those who want to celebrate a milestone occasion and for families who often can only travel in summer months.)

An important and unique aspect of her service is not only that it is a personal relationship, but that she travels with her clients “virtually” from the day they depart until they return home! In other words, via WhatsApp and email, she is in constant contact in “real-time” to ensure that everything is going exactly as planned.

Read more about “Italy with Victoria” 2020 Tours!

Read more about Victoria’s “Italian Trip & Tour Design” Services!

Click the link to check out other episodes and see my list of the best podcasts about Italy.


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About the author

Living in the Caput Mundi and trying to decipher Italian culture for the English speaking world.

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