top of page

How To Self-Plan Your Trip to Italy

There are two camps of self-planners. The first camp is the dreamers, who listen to all the podcasts, watch all the Stanley Tucci/Somebody Feed Phil/Anthony Bourdain shows, and are inspired and excited.

The second group comprises people whose hearts skip a beat when they hear the word "Excel." They love to plan, research every detail, and compile it in an ever-growing Google Doc that should someday be archived in the Library of Congress. (It's that good.)

Both camps end up feeling overwhelmed and riddled with FOMO. Why? Because self-planning a trip to Italy is impossible if you haven't considered the experience. That is your experience, not Stanley Tucci's or your neighbor who said, "omg you have to go to Positano." (You don't have to go to Positano.) Before you get lost in your personal movie about Italy or start obsessing about train schedules, use these four ingredients to put your self-planned itinerary on the right track.

Engage with the familiar

Are you an avid hiker? Do you love to shop? Are you fascinated by ancient Rome, jewelry, cars, or mid-century design? Perhaps you’re a foodie or have a growing interest in wine. Think about doing the things you already love-- in Italy! If you're having trouble picking something, think about what you would do if you were traveling somewhere closer to home for a 3-day weekend. Would you be skiing, getting an expensive facial, or searching for the best taco truck in town?

Engage with the unfamiliar

What can you do and see in Italy that would be impossible at home? Don't reject the idea of history or say, "I don't want to spend 8 hours in a museum," to squash the possibility from the outset. There's no midterm to study for in Italy, but there is the possibility of learning something that might spark new fascinations and interests that could last a lifetime. (Also, nobody wants to spend eight hours in a museum.) I advise picking one monument, one thing, and diving in. See Michelangelo's David in Florence, then take a day trip to Carrara for a jeep tour of the marble quarries. Go to Pompeii paired with the best pizza of your life in Naples.

Plan an adventure

I always look for a note of adventure to inject into every itinerary, which will mean something different to everyone. Maybe it's snorkeling among sunken Roman ruins in Baia, or it could mean trying a tripe sandwich in Florence. Perhaps it means skipping Florence, Venice, or Rome for... Ascoli Piceno. It's a gorgeous small city that isn't on the mass market tourist radar, and thank goodness for that because it feels like Italy's best-kept secret. Whatever your adventure, I guarantee it will be the experience you think about the most post-trip.

Plan for sufficient downtime

Everyone wants to maximize their time, but you will benefit far more from days with squishy room around them than by trying to see as much as possible. If you are traveling with friends or family, days 5 or 6 will be right about when you get sick of each other. Or you need some downtime to sit in a piazza with gelato and stare at a wall. Time to wander and rest leaves room for Italy's magic to show up.

It’s easy to be overwhelmed and want to do everything. You can never exhaust Italy’s treasures in ten lifetimes, but you can plan a trip that suits you perfectly when focusing on experiences first.


Need one-on-one help with your self-planned itinerary?


bottom of page