I’m an awkward traveler.  There are more mishaps and self inflicted bumps in the road than I care to admit when it comes to getting to and from my desired destinations.  Here are my worst travel blunders, and more importantly, how you can learn from them.

10 years ago I was traveling to New Orleans for a dear friend’s wedding.  I headed to the airport for an early morning flight departing from one of the easier (ie, quickest) airports ever I’ve traveled from.  I showed up to the check in counter ready for the first leg of my journey, but I was informed that I was too late.  I had arrived after the check in deadline, by 3 minutes.  Even though I was not checking a bag, used my most polite tone, and even as the plane was still boarding, there was nothing that could be done: rules were rules.  I was rebooked for a later flight.  My next flight was delayed, and I missed my connection.  I was put on the next flight that had me getting to New Orleans a lot later than originally planned.  I ended up changing in the airport and taking a taxi straight to the wedding.  I rolled up with a suitcase to the ceremony, right before the bridesmaids were going down the aisle.

Lesson learned: Check in online 24 hours in advance.  And, avoid non-direct flights if you are cutting it close.

I recently booked a hotel through booking.com for a Scotland trip.  I found the perfect Edinburgh location on a map, cross checked the reviews, and even uncovered a discount code that worked.  Moments after hitting confirm, I thought it was a little strange that I had received two confirmation emails from the hotel, but chalked it up to a technical error.   A few minutes later, I read the emails again and noticed I had two different confirmation numbers: I booked the same hotel room, on the same day, exactly twice.  The worst part? I opted for a non-refundable rate.  Panic set in.  I immediately emailed the hotel directly, nervous they would not be able to resolve my issue since I booked through a third party.  Thankfully, the manager was responsive and confirmed I had booked two of the same hotel rooms.  After they asked how many rooms I meant to book (one), the hotel canceled one of the reservations for me, without any charges.

The lesson: Pay attention to the confirmation emails so you can act quickly if needed.  Time is of the essence.

One of my earliest travel lessons was my first summer abroad, when I had to pack for 10 weeks, and brought along a 50+ pound suitcase.  Not only did I have to drag that monster around on weekend trips, but the piece de resistance was taking it with me on a 10 day excursion around Italy.  That trip had multiple stops with multiple hotels, which meant multiple trains, buses, taxis and planes.  There are also budget airlines like RyanAir that will charge an exuberant fee for any bag that weighs more than 25 pounds.  After that trip, I planned what I was bringing through the lens of what I may have to drag around cobblestone streets or stairs in hotels too old/charming to have elevators.

The lesson: Pack a few days early, then go through and remove duplicates and extra items you may not need.  You can always buy anything else, or borrow outfits from friends.

Last fall, I was once again flying to a friend’s wedding the morning of (when will I learn?)  I went direct this time, and had enough of a buffer planned that I could Uber to the hotel, get ready for the wedding, have a drink at the bar, and leisurely get to the ceremony.  I breathed a sigh of relief as we left the gate on time.  That relief was short lived as we lingered on the runway for an hour, not leaving the ground.  Once we did take off for what should have been a 45 minute flight into New York City, I noticed the plane circling: the pilot informed us we were in a holding pattern until the traffic on the ground cleared and we had a place to land.  Once we were on the ground, the plane sat for another hour waiting for a gate to open up. Yes, it was painful to be able to see the gate but not get off the plane.  I did my makeup on the plane to save some time, and ran to an airport bathroom to plug in my curling iron and do some last minute damage control.  I am not making this up - none of the outlets were working.  I threw the curling iron in my bag, hopped in an Uber, where I changed into my dress and shoes, and went straight to the ceremony. And did I mention that I found out on the way to the ceremony that my ex boyfriend and his new girlfriend would also be there?

Lesson learned: Airport lighting is not the ideal lighting, but I was relieved my makeup and outfit were within close reach while on the plane.

Stay tuned for Part 2!