7 Things That Self-Sabotage Your Italy Travel Planning

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Let’s talk about the most common ways people accidentally sabotage their Italy travel plans—so you can avoid them and actually enjoy the trip you’re dreaming of.

You already know I love slow, authentic travel in Italy.

I’ve built my life around it. I have a home in Lucca, I travel year-round, and I help others create meaningful experiences that go beyond tourist traps.

But I’ve also seen how even well-intentioned travelers end up overwhelmed or disappointed.

Sometimes, the problem isn’t Italy. It’s how the trip was planned.

Slow, immersive, local travel is deeply rewarding. But it’s not without its challenges.

Let’s make sure you’re ready for both.

1. You Overload Your Itinerary

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I know why you’re tempted.

You don’t know when you’ll be back. You’ve waited years for this trip. You want to see everything.

So you pack in Florence, Rome, Venice, Amalfi Coast, maybe even a few hill towns… in 10 or 12 days.

But here’s what happens:

• You spend 3–5 hours every few days checking out, dragging bags, catching trains
• You’re constantly watching the clock
• You miss out on moments that aren’t scheduled—those little, spontaneous experiences that make Italy special

This is one of the biggest regrets I hear. “I wish we had stayed in fewer places.”

If you want real experiences—like chatting with a barista in the morning or wandering through a weekly market—you need to slow down. That doesn’t happen when you’re always on the move.

Try this instead:

• Choose 2 regions max for a 10–14 day trip
• Pick 1–2 home bases per region
• Use day trips to add variety without repacking

When you stay longer in one place, you actually see more—not just with your eyes, but with your whole self.

2. You Plan for Your Ideal Self, Not Your Real Self

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Trip planning brings out the dreamer in all of us.

We imagine ourselves waking up early, exploring ancient ruins, learning to make pasta, biking through vineyards… all in one day.

But be honest:

• Do you like getting up early?
• Do you enjoy group tours or do they wear you out?
• Will you be okay walking 20,000 steps on cobblestones in the summer heat?

One of the fastest ways to burn out is to plan a trip for a version of yourself that doesn’t actually exist.

Here’s what that looks like:

• Booking back-to-back museum visits when you don’t really like museums
• Choosing cooking classes when you don’t actually enjoy cooking
• Scheduling early morning transfers when you prefer slow mornings

The trip will be better if it matches your energy, preferences, and interests—not someone else’s.

What to do instead:

• Leave space in your itinerary for downtime
• Plan for your travel rhythm (Are you slow mornings? Afternoon explorers?)
• Mix structured activities with free time

Your trip should feel like a better version of your everyday life—not a performance.

3. You Try to Please Everyone

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This is especially true for couples or families.

One person wants history. One wants beach time. One wants wine. And one just wants to relax.

You try to do it all—and end up doing none of it well.

When everyone compromises, sometimes no one gets what they actually wanted. And resentment builds quickly when you’re jet lagged, overheated, or hangry.

What I recommend:

• Talk about priorities before you book anything
• Let each person pick one must-do
• Set expectations around pace and downtime
• Consider splitting up for a few hours some days

You don’t have to be joined at the hip. One person can visit a church while another explores a food market. Meet up for lunch and share your stories.

I once helped a couple plan a trip where she did cooking classes and olive oil tastings while he focused on cycling and photography.

They were both happy—and came home with great stories and shared memories.

4. You Ignore Regional Differences

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Many travelers see Italy as one destination. It’s not.

Italy is a collection of very distinct regions—each with its own pace, culture, cuisine, dialect, even architecture.

Tuscany isn’t like Sicily.

The Dolomites aren’t like Puglia.

Train schedules vary. Local attitudes vary. Even the daily rhythm can change.

When you treat Italy as if it’s all the same, you risk frustration.

Here’s what I mean:

• Booking a trip to Liguria expecting sandy beaches (they’re mostly rocky)
• Planning to rely on trains in rural Umbria (you’ll need a car)
• Assuming every restaurant serves pizza (it’s not a thing in some areas)

What to do instead:

• Research regions before choosing where to go
• Think about your interests—food, art, nature, history—and pick regions that match
• Understand transportation options for each area

If you’re dreaming of wine tastings, rolling hills, and slow meals—Tuscany or Piedmont might be right. But if you’re craving seaside views and baroque towns, you might love Puglia or the Amalfi Coast.

Pick a region that fits you, not just what looks pretty on Instagram.

5. You Wait Too Long to Book Key Pieces

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This is one that sneaks up on people.

You start out thinking you have plenty of time. You’re researching. Comparing. Reading reviews.

Then suddenly, the flights go up. That boutique hotel is full. The cooking class you wanted? Sold out.

Italy rewards early planning—especially if you’re traveling in high season (May–October) or around holidays.

Here’s what you should book early:

• Flights (as soon as your dates are set)
• Accommodations (at least 3–6 months ahead)
• Train tickets for long-distance routes (Frecciarossa, Italo)
• Car rentals if you’re driving in the countryside
• Museum tickets (like the Uffizi or Vatican Museums)
• Guided experiences (food tours, day trips, cooking classes)

Why it matters:

• You’ll have more options
• You’ll avoid last-minute stress
• You’re more likely to stay in authentic places—not whatever’s left

I always tell my readers: the places worth staying in usually aren’t available last-minute.

6. You Skip Travel Planning Basics

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This is the boring stuff that makes a big difference.

I know—it’s more fun to plan where you’ll eat than to research whether there’s a train strike.

But skipping the basics can cause real problems:

• Getting fined for not validating a train ticket
• Booking a rental car and not knowing about ZTL zones
• Arriving at a museum only to find it’s closed Tuesdays

Even small things can throw your day off if you’re not prepared.

Some essentials to check:

• National holidays and local festivals (some towns shut down entirely)
• Museum and attraction hours (they vary a lot)
• Local transportation quirks (regional trains vs high-speed trains)
• Currency and ATM access (some small towns are cash-only)
• Time needed to transfer between trains (don’t cut it too close)

Also—learn what a ZTL is. Driving in one without a permit can get you a ticket months later when you’re back home.

I’ve had readers message me in panic over fines or missed trains. All avoidable with a little prep.

7. You Assume Off-the-Beaten-Path = Easy

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This one’s personal for me. I love getting off the beaten path. It’s why I live in Lucca—not Rome or Florence.

But let’s be real: The further off the path you go, the more planning you need.

Smaller towns and rural areas can mean:

• Few (or no) direct trains
• Limited dining options, especially on Sundays or Mondays
• Little English spoken
• Early closing times
• Fewer taxis or ride services

It’s not a problem—it’s just a different kind of experience.

How to make it work:

• Rent a car if public transport isn’t reliable in the area
• Learn a few key Italian phrases (or take a short course before you go)
• Book meals and tours in advance—especially in low season
• Be flexible. These areas move at their own pace

Some of my favorite stays—like a masseria in Puglia or a wine estate in Tuscany—weren’t easy to reach but they were unforgettable.

You just have to know what you’re getting into. Authentic doesn’t mean convenient. But it does mean meaningful—if you’re ready.

Final Thoughts

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Planning your Italy trip should feel exciting. But that excitement can turn into stress if you try to do too much, too fast, or too perfectly.

Here’s what I want you to remember:

• Slow travel isn’t just a vibe—it’s a strategy
• The best trips match your reality, not your fantasy
• Early decisions give you freedom later
• Researching the not-so-fun stuff makes the fun stuff actually happen
• Going off-the-beaten-path is worth it—but only if you’re prepared

You don’t need a perfect itinerary. You just need the right one—for you.

And if you want more help planning a trip that fits your style, I created a free 9-day email series that walks you through the steps.

From choosing the right region to what to pack, it’s designed for travelers like you—who want a slower, more personal experience in Italy. Let’s make this trip one you actually enjoy—not just survive. Sign up below! ⬇️

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