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Over the past few weeks, I’ve been helping several travelers prepare for upcoming trips to Italy. Interestingly, most of the questions haven’t been about Rome, Florence, or Venice. Instead, they’re about what traveling in Italy is actually like once you arrive. Questions like: How much should I pack? Should I rent a car? How much cash should I carry? How much time do I really need? Here are a few things that often surprise first-time visitors. Everything Takes Longer Than You ThinkOne of the biggest mistakes travelers make is assuming travel days are as simple as they look on paper. That train from Florence to Bologna may only take 38 minutes. But you still need to: • Get to the station
• Find your platform
• Wait for boarding
• Navigate crowds with luggage
• Get from the destination station to your hotel Suddenly, that “quick train ride” can easily take half a day. My advice? Leave more breathing room in your itinerary than you think you need. Italy is much more enjoyable when you’re not rushing. Pack Less Than You Think You NeedItaly is beautiful. It’s also full of stairs. Historic hotels. Train stations. Apartment rentals. Hill towns. And when you do find an elevator, it often feels like it was designed for two people and one suitcase… if everyone stands very close together. A lighter suitcase makes every part of the trip easier. Slow Travel Always WinsWhen travelers ask whether they should add one more destination, my answer is usually the same. Probably not. Three nights in one place is almost always better than one night in three different places. The moments people remember most aren’t usually the train rides or checklists. They’re the unexpected discoveries. A quiet piazza. A neighborhood wine bar. A conversation with a local. An evening walk that wasn’t planned. Those experiences only happen when you give yourself time. Every Town Doesn’t Need To Be A HeadlinerOne thing I often tell first-time Italy travelers is that not every stop needs to be famous. Some travelers spend months trying to determine which village is the “best” village or which town is the “must-see” town. The truth is that much of Italy feels special. Whether you’re in Florence, Bologna, Verona, Montepulciano, Pienza, Lucca, Orvieto, or a small town you’ve never heard of, you’ll often find the same things that make people fall in love with Italy. Historic streets. Beautiful architecture. A local café. A lively piazza. A glass of wine as the sun begins to set. Rather than treating Italy like a checklist, try treating it like an experience. Slow down. Sit a little longer. Wander a little farther. The goal isn’t to see everything. The goal is to be fully present wherever you are. One Final ThoughtItaly isn’t a destination that rewards rushing. The train schedules, the long lunches, the evening passeggiata, the conversations in the piazza—everything seems to encourage you to slow down. The best Italy itineraries aren’t the ones that see the most places. They’re the ones that leave enough room to truly experience the places they visit. That’s where the memories are made. Buon Viaggio, Dan Eubank Nomad With Dan P.S. If you’re planning an Italy trip, consider building in more time than you think you’ll need. Italy rewards travelers who slow down. If you’re planning an Italy trip, you may also enjoy these destination guides: Explore Rome → Explore Florence → Explore Tuscany → Explore Verona → Also confirmed: long lunches in Italy are still undefeated. “Planning Italy becomes a lot easier when you have someone helping you slow things down and experience it more intentionally.” Start Planning with Me → If you ever reply to this email, it comes straight to me.
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