Travel Planning: This Isn’t Your Last Vacation In Italy!

I’d love to claim that my views on traveling to multiple cities during a single, average length vacation have developed over the years, but the reality isn’t so. I have gotten tired, or more accurately uninterested, in multi-leg travel beginning after only a couple trips abroad. 

For me, the right number of cities to visit is: 1, but with a notable exception. The balance between having beautiful experiences in a new city and minimizing the frustrating exhaustion of repacking every day or two has definitely tilted in the direction of minimizing the frustration. Diving deeper into a single city, still with the possibility of a day trip, has been the best trip planning experience for us for years now. This is also without FOMO (the fear of missing out).

This Is Not Honest Travel Planning

For many years now, Mrs. Curmudgeon and I have enjoyed travel videos. Years ago, it was more of the Rick Steves and Lonely Planet style of travel, but today our attention is drawn towards vloggers that travel globally and post their trips online. These have been our favorites for quite some time.

When I watch these well organized and fearless travelers of the sky/van/boat/car, I am enchanted by the idea of traveling around the world, staying a couple days in one location, then moving on. They seem to really enjoy it, so why shouldn’t I? Then, the truth hit me like a lightning bolt: there is dishonesty in social media and they are intentionally not showing the downsides of this style of travel.

Once I accepted the fact that I can enjoy watching a travel vlogger while at the same time having no interest in trying to live their lives, a calm swept over me that only a self-satisfied curmudgeon like me can truly understand. I’m happy with how I live my life, even if I am still interested in watching how others live theirs online.

So, How Should I Plan My Itinerary?

When I mentioned above that my magic number of cities that I want to visit on a single vacation is 1, that isn’t the entire story. The exception is with day-trips. Fitting in a day trip to a neighboring town without checking out of your hotel or B&B is a simple enough endeavor that it should definitely be included in your itinerary.

The biggest annoyance for me with multi-city travel is packing, unpacking, carrying the luggage, putting it in the overhead and dragging it over the cobblestones. Checking-in, unpacking our bags, meeting new landlords (or property managers) and restocking the refrigerator all add to the frustrations, but the packing/unpacking is what really pushes me over the edge.

The magic of a day-trip is that it allows you to keep a home base and still experience an unexplored nearby city. It might not seem like it, but I like train travel. I’ll happily ride the rails somewhere hard to reach because the trains in Europe aren’t like those in the US (read: “Better”). Heading out on the morning train from Rome to Orvieto is a great day-trip since you can be snug in your Rome hotel bed the same night.

There are quite a few other day-trip worthy towns around Rome that can enhance your travel experiences without the necessity of moving your home base. This way you can hunker down and explore the hell out of a place for a much longer stretch of time.

When You Plan Your Trip, What Is Your Right Number?

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