This is how to plan your Italy trip in 2026

This is how I'll be advising my clients for the year ahead

Something is brewing in our popular culture that makes me very optimistic. (When was the last time you heard someone say that?) The proliferation of AI slop and a general feeling of being over-dopaminized is inspiring people to seek quality. It’s reflected in the marketplace, with heritage brands returning to the products and aesthetics they were built on (Ralph Lauren, Burberry), and people are reclaiming their attention spans by reading real books again.

It is also clear that the elite are more interested in the humanities than they have been in decades. The drumbeat of STEM and “teach them to code” is fading. Folks, we are on the verge of a Renaissance, and I have been waiting in the dunes for this my entire life.

These are portraits of elite Renaissance citizens painted on the walls of the Brancacci Chapel. When Florence achieved extraordinary wealth, the city became more unstable and the future uncertain, which in part instigated the Renaissance and the studias humanitatas. They believed the study of the ancient world would yield great wisdom, and they educated their children accordingly.

I’ll talk more about it in an upcoming podcast episode, but first, I'll offer some insights for planning an Italy trip in 2026 and share the upcoming dates for the monthly Ask Me Anything About Italy and Destination Deep Dive.

If you want to use AI for trip planning, this is how to do it:

I fully embrace several AI tools in my business and life. I’m also closely tracking the content on my own website to see what ChatGPT and Perplexity pick up. Here’s where I am on it’s use as a travel planning tool:

1. It’s ok for the most popular places. Not amazing, but ok. You get a very breezy overview of what’s possible, but without critical logistical details. It might tell you to visit the Colosseum and the Vatican in one day without telling you a) that’s a terrible idea and b) you'd better have skip-the-line tickets for both, purchased months prior.

2. It’s not bad if you’re trying to figure out transportation along major routes, between major cities, or along major highways. It did hallucinate a train from Florence to Ascoli Piceno, so make sure you check everything against actual train schedules, not Rome2Rio or even Google.

3. It’s very bad for the less popular places.

Though AI is improving daily, I don’t expect its utility for Italy trip planning to change drastically for the better, given everything I wrote about in Why You Should Never Ever Trust an Italian Website. For AI to be genuinely valuable for your trip planning, be very specific in your prompting and ask lots of follow-up questions.

Here’s an example of what I mean…

I asked Perplexity for the five best restaurants in Rome. The results were three Michelin-starred restaurants and two spots where getting a reservation is a blood sport. That’s because “best”, along with “authentic” and “luxury,” is now a meaningless word.

I refined my question and asked for five restaurants in Rome that serve traditional Roman cuisine and are beloved by locals. The answers were much better; I still have my criticisms of the choices, but hey, I’m a tough audience. Mostly, I gave side-eye to the citations where the responses originated.

To raise the standards, I asked Perplexity to review respected Italian-language media for recommendations. I was much happier with the results.

The good news is that if you ask ChatGPT, Gemini, or Perplexity very specific questions — five gluten-free restaurants in Florence, or all the places where Anthony Bourdain ate in his Rome episode of Parts Unknown — you’ll get helpful information.

I’ve sent many clients to Osteria del 1931 in the Monteverde neighborhood of Rome, usually busy with locals and diehard Bourdain fans.

Will any of this save you time? Not really. It’s just another tool. A conversation with someone who has lived experience is the ideal option.

Right now, the exchange rate stinks for Americans

Every morning, I get an exchange rate update from Wise, and it’s been a daily groan. So you’re going to want to deploy your money well. Decide how much you can afford to spend, then design your trip. That’s how to get it right.

Higher costs might initially make you want to cram in as many things as possible to maximize the experience. However, you’ll end up spending more money and time on physical travel than on rich experiences. My advice is to reduce the number of places you visit. Fast trains are amazing, but expensive, and you still need to get to the train station on both ends of your transfer, so you’ll be racking up taxi fares and eating train station sandwiches. Italy deeply rewards the less-is-more philosophy. Pick your places, then find all the books, movies, and podcasts about them and start traveling well before you board your flight. For seven days, visit no more than two places. For 10, the maximum should be 3. Consider the distances between them as well.

Invest in quality

Exquisite leather gloves made in Naples in the neighborhood called Rione Sanità

Speaking of going deeper, if you choose to visit just one or two places, you should also consider bringing home something memorable. Perhaps a vintage Fortuna pendant from one of the gold shops near Campo di Fiori, or a truly special piece of Venetian glass. In Florence, visit a paper marbling artisan and wrap next year’s Christmas presents in it. In Naples, invest in a pair of artisan leather gloves.

A lot of the best outlet shopping is not near Florence, but just outside of Turin. In the Le Marche region, where most of the best Italian shoes are crafted, there are plenty of outlets as well.

In Irpinia, stock your cellar with Aglianico, called the “Barolo of the South” for its aging potential, most of which is unavailable to purchase abroad. Every time you open a bottle, you’ll have beautiful memories and stories to share. Bring home something that continues your Italian experience.

What’s coming up

The next Ask Me Anything About Italy Zoom call will be on January 8th at 8 pm ET. This is where paid subscribers gather to ask all their trip-planning questions, though more and more often, people are coming to listen, get ideas, and just hang out. (Which I love!) If you can’t attend live, you can email me your question, and you’ll hear the answer in the replay, which is sent the following day.

Then on January 22nd at 8 pm ET, I’m premiering the Venice Destination Deep Dive. More than any other Italian city, the information available about Venice is bad. The biggest problem Venice faces is not overtourism but hit-and-run tourism, leading most travel advice to suggest that Piazza San Marco, a glass of prosecco, and a gondola ride are all you need to see in Venice before getting on the fast train to Florence. Ohhhh, how wrong that is, and I’ll show you exactly why on January 22nd.

The "X marks the spot" location is definitely included in my Venice Destination Deep Dive.

If you’d rather have my team and me plan your trip, take a look at my menu of services. I have everything from one-off Trip Consultations to full Bespoke Trip Planning. Trip planning season officially begins next week, and we would be so happy to design a completely customized Italy experience for you.

Thank you so much for reading, and if you like what I’m doing here, I would so appreciate it if you could spread the word.

Buon anno e ci vediamo presto!