After a year of no travel, I am beyond excited to get started on a summer filled to the brim with travel. On the agenda for the summer? The UK, Hilton Head Island, road trip to Maine/Prince Edward Island, and San Francisco. All of this starts with a sampler in Chicago which, when this post publishes, is where I am.

All of this travel will be done on a teacher’s salary following a year with short stints of unemployment. Although I will be using my credit card, I will not be going into debt. The spending is all backed up with my dedicated travel savings account aided by frugal travel hacks I have picked up over the years.

The tentative posting plan is as follows. Since each trip is slightly different, I plan to write about how I planned and prepared for each trip. After the trips I want to write about the execution of the plan and how I dealt with the inevitable unexpected. I also hope to have my writing chops up to par and ready to write about my experiences and the history of all that I am privileged to visit.

This trip started to take shape on a whim. Some time last year I thought “hey, since Laura lives in Chicago now, maybe we could go visit over Spring Break.” Dad and I actually started brainstorming the trip before telling Laura. Whoops.

The trip existed in hypothetical form only for several months due mainly to my school schedule. I wrote down “30 minutes at least travel planning” in my planner on every Saturday so far this year but have yet to be able to follow up with that. (I hope to change that since the UK trip cannot be planed on such a whim as this trip.)

Even with my schedule working against me, the trip gradually started to take shape. First, I set a budget, $1000. I also established that on this trip, unlike all previous trips with Dad, we would go Dutch on everything. This means that more money comes out of my pocket but less is spent on the trip overall. All our previous trips were graduation gifts.

Second, I purchased tickets or the must sees and airfare. Those must sees included White Sox, Cubs, and Hamilton tickets. Unfortunately, we will not be able to see Hamilton. That story comes a little later.

I couldn’t purchase the baseball tickets as soon as I wanted since the regular season tickets were not released until early March. I could still see the schedule which helped plan the flight dates. The White Sox played at home through Sunday the 9th. The Cubs played at home for most of the rest of the week, including April 15th, Jackie Robinson day.

This schedule did add an additional expense. Laura had people staying at her apartment through the weekend. That meant that we needed a hotel for two nights.

When I could finally purchase the baseball tickets, all of the affordable Cubs tickets for the 15th had vanished. They are the reigning champs after all. We’re going on Thursday.

I clicked from there to Hamilton tickets. My jaw dropped at the prices. Of course, I expected them to cost more than the baseball tickets but at $300 each, a single ticket would use up just under a third of my total budget. Then began the internal battle. How much did I really want to see Hamilton?

I had just started listening to the soundtrack on repeat-late to the party I know-and am obsessed. This is something that I sincerely and completely want. I also received a larger than expected tax return which helped me talk myself into taking the plunge. Then Dad sent me a Facebook message; Hamilton is coming to the Peace Center in 2018. Decision made. I’m not happy with having to wait but it’s the logical, financially-wise thing to do.

The story does not end there. Laura came to visit a couple weeks ago and commented that it was a bummer that we weren’t going since Wayne Brady was init. Immediately I set to work looking for tickets again. Wayne Brady as Aaron Burr? Yes please! I found some tickets and prepared to purchase them. Then I thought to check on the end date of Brady’s temporary run. It ended on the 9th. The tickets I found were for the 12th. Tickets for the two possible showings we could have attended were $100 or more above what the other tickets cost. Back to waiting on 2018.

When I initially decided against the Hamilton tickets, I looked for something else and discovered the symphony. For significantly less than a Hamilton ticket, I get to take in a performance by one of the best orchestras in the world.

Third, after I purchased the tickets, I planned the rest of the daily activities. Unlike most of my other trips, I planned only minimal daily activities. The primary reason is a culprit that I have mentioned a few times already, lack of time. The secondary reason flows indirectly from the primary. Work has been fairly crazy so the idea of packing in as much as possible felt counterproductive. I want to both rest and to explore.

Planning each trip, although similar at times, takes on a life of its own. This is the first trip I have planned since returning to teaching. I hope to apply what I learned to the rapidly approaching UK trip.