Which Italy Is Right for You? A Free Session for Curious Travelers

Are you a razor clams on the beach person or the boiled meat and dumplings type?

Last March, I was fortunate to see an exhibition at the Palazzo Madama in Turin that brought together more than 200 posters and guidebooks from the early 1900s. In particular, I was captivated by how effectively each of these posters conveyed the character and vibe of different Italian cities and regions, and how useful they are today for precisely that.

Today, Italy is relentlessly marketed as la dolce vita, spritzes at sunset, a Vespa ride with a chestnut-haired hunk, and pasta that doesn’t make you fat. And yes, that Italy is most certainly for sale, but I much prefer the nuanced, complex Italy that is more accurately twenty different countries, each with its own cuisine, history, and even language.

You can see this right now if you’re watching the Winter Olympics coverage from northern Italy, which has Alpine landscapes and lots of boiled meat and dumplings. That’s Italy, every bit as much as Sicily’s black sand beaches, where you can eat razor clams fresh off the boat. Planning a trip without understanding how different Italy is from region to region is setting yourself up for either getting ripped off or being sorely disappointed.

Sometimes you want a trip that’s nearly frictionless: well-organized, easy logistics, clear expectations, maybe even a quasi-resort experience. Other times, you want to explore and have experiences that you couldn’t have anywhere else. Both are valid. What’s hard to know from searching online is which regions, cities, and price points actually align with who you are as a traveler.

So I’m hosting a free live session called The Italy Vibe Check to help you understand what you’re truly signing up for, before you book a trip. I will provide clarity on the most famous places and share the less well-known ones. (That’s what I do best.)

Date: Monday, February 16
Time: 7:00 p.m. Eastern Standard Time

This session is especially for those of you in the early stages of planning an Italy trip whether it’s a once-in-a-lifetime “see all the big sites” journey or your second, third, or fourteenth trip.

I’ll discuss:

• How to think about the “big four” cities—Florence, Venice, Rome, and Naples—honestly: yes, they’re super crowded, but with the right expectations and timing, they can still be extraordinary.

• How to plan your trip to Italy based on your preferences. Do you want coffee and cashmere Italy, or spaghetti and hot springs Italy? Do you want castles and museums or temples and catacombs?

• The “under-the-radar” places that are actually the best.

• I’ll also address pricing, as this is one of the least transparent parts of trip planning. I’ll walk you through what’s realistic across different regions and travel styles, so your budget and expectations don’t contradict reality.

How to join the Italy Vibe Check

To keep things simple, the Zoom link will go out only via this newsletter.

• If you’re already a subscriber (free or paid), you don’t need to do anything right now. On Monday afternoon, I’ll email the Zoom link to all subscribers. Click on it at 7 pm, and I’ll see you there.

• If someone forwarded this post to you, and you’d like to join, please hit Subscribe so the link lands directly in your inbox. Free or paid, either way, you’re invited.

For paid subscribers

For those of you already supporting this work as paid subscribers (thank you!), we also have our regular sessions this month:

• Monthly Q&A on Zoom

  • Date: Thursday, February 12

  • Time: 8:00 p.m. Eastern Time

• Destination Deep Dive: Amalfi Coast

  • Date: Thursday, February 26

  • Time: 8:00 p.m. Eastern Time