Two Ways to Plan a Trip and Keep Your Sanity!

Chicago Neighborhoods

Enjoy a fulfilling trip and skip the need for a post-vacation vacation? Yes, Virginia, it’s true – you can have both!

I’ve been on (and even planned) my share of trips that employed laser-sharp adherence to the almighty schedule. Woe to those who wanted to wander to somewhere not part of the original travel plans.

Well, in short – that stuff is for the birds. I’m here to enjoy my days, not feel like I’m beholden to them!

Especially as I’m traveling full-time these days, I needed to find a way to get in all the touristy stuff and other activities without stressing out with what to do when. This system works.

Now whether you have a weekend or a week coming up for your next trip, chances are you have ideas about what you want to do during your time there. Here’s a way to see as much as you want and feel like you still have a choice in what you’re doing.


Step ONE

Write down EVERYTHING you want to do. This include friends to visit, destinations to see, restaurants to eat at, entertainment to take in, classes to hit up, and anything else you can think of. I recommend using a file on your computer, as you’ll be making multiple edits and moving things around.

If you’ve never been to that spot, research it online or solicit advice from friends and family: what are the “can’t miss” experiences of where you’re headed? Add it all to your list.

Your list may start to look a little overwhelming. That’s OK. You won’t be doing everything. This is just a way to collect all the info.

For my curent trip to Chicago, here’s part of my list…

  • Take in a Cubs game at night
  • Rent a bicycle and hit Lake Shore Drive
  • Mike & Kristin near Wrigley Field
  • Visit Millennium Park and the Bean
  • Meagan & Jock in Gold Coast
  • Visit friends in Oak Park
  • Museum of Contemporary Art – FREE on Tuesdays
  • Gino’s East – multiple locations
  • Bekah at Moody Bible Institute
  • See Obama’s house in Hyde Park (bonus points: get tackled by secret service)

Now to me, this list is just a big mess. Sure, there are specific items, but things are all over the place, geographically speaking. Add into this the fact that I’ve never been to Chicago and the city has about 4000 neighborhoods (no need to fact-check that one), and I just don’t know where to start. Don’t get me wrong – wandering around the city with no plans can be fun – it’s just not how I want to spend every day.

Step TWO

Here’s where you get control over the itinerary.

Go through your entire list and break up everything by neighborhood or section of town. Are some items downtown? Near the ocean? Is that restaurant you want to try near where your friends live?

The point here is to group everything so that you have IDEAS for possible itineraries, not rock-solid plans. Leave the minute-by-minute schedule of activities for wedding planners; rather, as your days change or take a different turn (they always do), you can glance down at your list, reference the area you’re now in, and then pick a place to start!

Again, for my list in Chicago, here’s a sample…

    • Museum of Contemporary Art – FREE on Tuesdays
    • Lookingglass Theatre Company
    • Meagan & Jock
    • Bekah at Moody Bible Institute
    • Chicago History Museum – FREE on Mondays
    • Lincoln Park Zoo – FREE
    • Second City Improv
    • Gino’s East
    • Art Institute of Chicago – FREE on Thursday nights
    • Millennium Park
    • Gino’s East
  • HYDE PARK (a bit south of the city)
    • Obama’s House
    • University of Chicago
    • Museum of Science & Industry

Now everything is much easier to manage, and I can use this in at least a couple ways:

  1. I can plan days based on sections of town. Perhaps for one day, I’ll check out the Gold Coast and Lincoln Park, as they’re relatively close.
  2. If I suddenly find myself with extra time, I can look down at my list, see what I’m near and go! Where I stay often shifts from night to night, so having all this categorized really comes in handy as I look ahead to the coming day.

In the past, I’ve also used this space to include information on public transportation (how late does it run, what do transfers cost, etc), special events happening (festivals, fairs, concerts). Set it up however will best work for you.

I use the TextEdit program (Notepad on a PC), as it keeps this info simple and easy to read. Obviously, if you want to get all stylistic with it, feel free. I store the file right on the desktop of my Macbook Pro, so I can access it quickly, whether I’ve found a wireless signal or not.


How about you – how do you plan for trips and keep your sanity?

I’d love to hear your ideas, comments, and suggestions.

Until next time,



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Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad - looking to improve myself, have fun and serve others.