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HOW MUCH PLANNING 
IS TOO MUCH PLANNING?
 
We plan a lot. Like, a lot.
 
Flights, trains, apartments, check-in times, check-out times, neighborhoods, transportation, how one stop connects to the next. When you're traveling full time, there's just too many moving parts to leave everything up to chance.
 
But we've also figured out there's a point where planning stops actually helping.
 
If every single day is already spoken for before we even arrive, we usually end up changing it anyway. We get tired. The weather turns. Something takes way longer than expected. We stumble on a part of town we love and want to go back. Or honestly, we just don't feel like doing what we planned.
 
That's where over-planning starts working against you.
 
We still like knowing where we're sleeping and how we're getting there. We like having the big stuff handled before we show up. But we don't need every museum, restaurant, market, and day trip mapped out weeks in advance.
 
Some of that's just experience talking.
 
When we first started doing longer stretches of travel, we figured a good plan meant having most of the trip figured out ahead of time. Now we'd rather leave enough room to change our minds.
 
That doesn't mean we roll in with zero idea what we're doing, though.
 
We still scope out what's nearby. We save places we might want to check out. We look into whether something needs a reservation. We make sure we're not showing up on a holiday when everything's shut. We just try not to turn all that info into a rigid schedule before we actually know how the place feels.
 
The longer we travel, the more we notice how much stuff you just can't predict from home.
 
You might think you want to spend a day across town, then realize your own neighborhood has way more going on than you expected. You might plan three day trips and decide after the first one that you'd rather just stay put. You might book something because it looked like a big deal online, then walk past ten things you'd honestly rather be doing.
 
We've just gotten more comfortable leaving gaps.
 
Sometimes the best plan is knowing what actually has to happen, and leaving the rest alone until you get there.
 
For us, too much planning is when the itinerary starts telling you how to spend your trip instead of helping you enjoy it.
 
We still lock in the stuff that'd be expensive or annoying to fix later. Everything else can wait.
 
When we started planning day trips out of Bologna, the train times made the choices look pretty simple. That's not exactly how it played out.
 
Scott & Liza
 
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Best Day Trips from Bologna — What We’d Do Again (and What We Got Wrong)
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