Fun with Vacation Planning | Tragic Comedy

I think I have discovered a new interest: Vacation planning. Most people enjoy daydreaming about possible future trips, but not everybody enjoys working out the fine nitty-gritty details of every last part of the trip. I have found that I do. I spent more time planning our honeymoon than our wedding, and even minor day trips take up inordinate amounts of my attention. For a just-concluded five-day visit by Kelly's brother Andy and his boyfriend Joe, I spent weeks of research and preparation. It paid off; we had a great time.

My philosophy of trip planning is that, once you're on site, it's easier to take something out of the itinerary than it is to add something in. I stuff every day of a vacation full of planned activities, and once we're there, if we're too tired or too stressed or otherwise not feeling like doing the next thing on our list, we simply skip it. I don't like to leave gaps in the plan where we could be doing something but we'll probably wind up sitting around doing nothing because inertia takes over.

Besides, filling every moment of the itinerary allows me to experiment with different arrangements that maximize our time -- for instance, by putting these activities in this order on day 1, and those activities in that order on day 2, we can squeeze out extra time for another activity that we'd otherwise have to miss. If I'm going to go to the effort and expense of traveling, I want to make the most of it. And of course, it's fun to think about the trip from every possible angle.

So far, Kelly has been a good sport, putting up with my questions about which activities and destinations she'd prefer, because she knows that I'm taking care of the research and reservations and other work. I fear that I control the process too much in the interest of having the best possible trip, but I have to trust her to tell me if I'm becoming a control freak.

What did Kelly and Andy and Joe and I do in five days? We hunted for seashells on the beach, fed flamingos in a zoo, drove up along the keys, played Mario Kart and other games at home to relax, rode roller coasters, saw an explosive stunt show, shopped for exotic foreign candy, watched belly dancers and hibachi chefs, and ate a huge variety of food. I'm not going to bother sharing photos as you've probably already seen them on Facebook (friend me if you haven't yet). The success rate turned out the same as other trips that I've planned extensively: Around 90% of the trip was fantastic, and the rest either couldn't be helped due to unforeseen issues, or fell victim to schedule-trimming on site. I couldn't be more pleased, and I'm looking forward to the next family visit already.

Next up: Kelly and I are going to New York City for a weekend this August. I'd better get started. :-)

Two Replies to Fun with Vacation Planning

Erik Bates | April 18, 2016
We just went to NYC a few weeks ago. Had the absolute time of our lives.

Chris Lemler | April 18, 2016
I heard it's a nice and a big place to go see

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