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 and friends, toasting to La Dolce Vita in PugliaWell, 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 Pros ​Generally cheaper​​​Meet lots of people​​See a large number of "checklist" sites​Wide choice of destinations Cons ​Overly-ambitious itineraries​ ​Time spent waiting on others​ ​Large chain hotels ​Tourist restaurants Conclusion:​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 fron​t of the greatest possible number of famous monuments. Usually cheaper, too.  ​Small Group Pros ​An intimate group, with easy access to tour leader​​Boutique hotels​​Family-run restaurants​​​​Unique experiences (ex. cooking class) Cons ​A bit more expensive than large groups ​​Some free time, but also some scheduled events Conclusion: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.