Simply Traveling: Adventures in vacation planning

* I wrote this entry before the creation of SimplyEvani but since it’s travel related, I decided to keep it!

Rob and I have taken all of our major vacations (and most of the minor ones) with other people. So as we embarked on the rollercoaster that was planning our own vacation, I was painfully unaware of how crazy it would make me. Luckily, Rob is always prepared for my insanity.

Daytona here we come!

First off, we had less than a month to plan a vacation in August. For me, that was like trying to fit an elephant in a suitcase, it’s just impossible. I was nearly content with spending my week of vacation sitting at home watching How I Met Your Mother reruns when I found a deal to Orlando, Florida through Flight and Hotel for 4 days as low at $309! Now it isn’t my first rodeo on a travel website and I knew that taxes would take it to around $380. But under $400 seemed viable and suddenly the race for a vacation began.

I started by mentioning it to Rob and gauging his response to this deal. In clearly an act of insanity, once Rob is in, I suddenly drop out. I start rationalizing all the ways that it isn’t fiscally responsible and how unnecessary a trip would be. Cue Rob for his next step, convincing me back into the vacation. For a few days, we dance back and forth mostly with me being gung-ho one minute and completely against it, all within the same short breath. One of my biggest flaws is my incessant need to research so I look up every viable hotel that fits with the deal and as soon as I’m enamored with a hotel, I start looking into reviews on Then within an hour, I completely hate the hotel and move on to the next. You can see how this drew out for a good 4 days as I wiped out a majority of the hotels available in Orlando, FL.

Since we’re walking distance, we’ll definitely be in Downtown Disney!

Much to my dismay, this cheap deal through was poised to end by midnight on Friday July 8. Come Thursday night, I singlehandedly researched my way into every hotel and scenario and was defeated. Rob comes over around 8 pm on Friday and takes the laptop. With me feeling dejected and overall beat from the experience of vacation planning, he finds a deal for a “Mystery Hotel located in Downtown Disney”. What this meant is that would not publish the hotel’s name and guaranteed a list of amenities with a fabulous price. This seemed like the perfect solution. I began to panic about what if the hotel was bad, or had tacky furniture or even worse had no pool. Much to Rob’s dismay, I managed to google search until I had a pretty good idea what this “Mystery” hotel was. More to save his sanity than my own,  I decided not to look into it’s reviews. I told him I was ready to book and we decided we were in.

DisneyWorld, here we come!

My voice rather shaky as I confirmed the details of our flight and hotel, I worked through my panic and gave into the madness. Yes, we were paying $468 dollars (flight, hotel and the cost of shuttles to and from the airport directly to our hotel). Yes, we were going on vacation alone. And Yes, it was basically non-refundable. Those points made me panic. But imagining the 5 days and 4 nights we’ll stay in our beautiful hotel in Florida, I could not be more excited! Our hotel has constant shuttles to all the DisneyWorld parks and we’re within walking distance to Pleasure Island and Downtown Disney. We’re planning definitely to stop by DisneyWorld, possibly the Wizarding World of Harry Potter and Daytona beach. Moments after booking and getting the confirmation, I had brief moments of panic, followed by Rob squeezing my hand saying we did good. It makes me feel good that making decisions in life will be so much easier and more enjoyable with him by my side.

Besides my car, I’ve never bought anything as expensive as this trip. My panic and anxiety comes from the fact spending $400 doesn’t come easily to me. Planning this vacation was a lesson in learning to let go for the sake of enjoyment and trusting that I won’t make poor financial decisions. I mean, the best part of living at home is being able to save for life AND save for vacations to enjoy it all along the way. All I know is that in the coming months, I think I’ll need a vacation from vacation planning!


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