My First Time

December of 2015, a few months after graduation, and after 3 and a half years of dating, I traveled for the first time with Kevin. We decided to go to Florida for the holidays so he could meet the majority of my family (for the first time). And also, tell them that we decided to move in together, no pressure!

The trip was pretty great, in the I can laugh at it now sort of way. Spending time with my family is always fun, especially since it’s not something I get to do as often as I’d like. And naturally, they loved Kevin. All the trouble was in the rest of the details. This being my first trip and all, I didn’t quite have the planning down. I was looking for great deals and paying more attention to the prices than the details.

What looks like a perfect fun-filled getaway, as social media portrayed, had a very rocky start. You know how they say a true test of your relationship is traveling together? I can vouch. It was all hugs and kisses until we tried to pick up the rental car. We went outside to look for it, excited to feel the warm sun, making plans to drive to Cocoa beach before we headed to the hotel. But, the car was nowhere to be found. After a lengthy and confusing conversation with the rental car company, we realized why we couldn’t find it. The answer was pretty simple. I rented it (nonrefundably) from the OTHER airport in Orlando…about 40 minutes away.

So, we had to pay for a shuttle. After about an hour of the silent treatment, we were on the way to our car. When we got there we had to buy a SunPass because apparently, that’s the only way to for pay tolls in Florida (what’s that about???). By the time we made it to our “hotel,” we were all made up and ready for a new fight. Our hotel ended up being more like a motel…a cheap motel. I was feeling pretty dumb and in a terrible mood. Kevin made me feel better about how sketchy our room was because, in reality, we weren’t spending that much time in it. And the sheets making me itchy was mostly in my head. And when it comes down to it, it’s impossible to be unhappy, when you’re in the happiest place on earth.

After spending New Year’s Eve in Orlando, we got to drive down to Fort Lauderdale (where my family lives) and spend a few days at the beach. The only downside was when we had to drive back at 2 am to catch our 7 am flight out of Orlando. Which, would have been fine. We were flying out of the airport I rented the car from! Except, it turned out that they didn’t open until 7 am. So, we had to take the car to a random car lot and order one terrifying Uber ride to the airport. The cherry on top.

My first-time trip planning failure came with its upside though. Thanks to the embarrassment, I’ve taught myself how to plan the perfect trip. We have to learn from our mistakes right?? With my astute, and recently acquired itinerary making skills, there’s no more much fewer hiccups.

Lessons I Learned

  1. Go by the airport codes, not the airport names!
  2. When you buy something cheap, often times you end up paying double.
  3. Animal Kingdom is my favorite Disney park (*unpopular opinion*)
  4. Orlando is extra magical during the holidays
  5. Harry Potter world is more awesome than I expected (and I expected a lot)
  6. If your relationship can make it through a botched family vacation, it can make it through just about anything.

30 responses to “My First Time

  1. I remember my first trip with my old roommate… she forgot to write down the name or address of our hostel and we had no idea where to go when we got to the bus station. I was so mad, I’m surprised we stayed friends 😛


  2. I totally agree with you that taking a trip together is definitely a good test of your relationship. I’ve taken a few trips with my long time boyfriend now and I can tell you right now it started out rough LOL. We’re much better at it now but travel can be very stressful esp. these days and it can bring out the worst in people so if you can stay cool headed and weather any storms then you’ll be good in the end. Thanks for sharing your story.

    Liked by 1 person

  3. My husband and I used to go portaging with friends for 9 days each year with our friends. The first year, they told us that if we didn’t have any arguments, there was something wrong, lol! We did, but we made it through, 17 years later😉

    Liked by 1 person

  4. I love going to Disney! And they’ve really worked on Animal Kingdom in the last few years. I’m a fan of the Lion King show in there 🙂

    Liked by 1 person

    • It was awesome! I grew up going to Disney, but apparently my family liked the other three more because I didn’t make it to Animal Kingdom until I was 22. Instant obsession!


  5. Haha, I can relate to travel disasters, but booking your rental at the wrong airport – that’s one I have yet to achieve! At least it wall worked out in the end and you’re right, learn from the mistakes!

    Liked by 1 person

  6. Along with travel, another thing I like to use to check with my friends is music. We share music to see if we have similar tastes or our view towards things. As for your story, all’s well that ends well 🙂

    Liked by 1 person

  7. I’ve been to Orlando A long time ago and it still one of the best trip I’ve done ! I need to go back for Harry Potter !

    Liked by 1 person

  8. Omg Florida is my favoritest place. I too love Disney animal kingdom . Most under rated. And yes if u can travel with ur guy … u can almost do everything together

    Liked by 1 person

  9. Pingback: How to Plan the Perfect Trip | Expat(ish)·

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