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INFO: The Travel Fuck Up - Ready To Fly, No Where To Go

After several years of rather aggressive travel, I often like to think of myself as a seasoned traveler. There's very little on the road that can frazzle me at this point in my life. Canceled flights? Long security lines? Pubic hair in the hotel bathtub drain? I'm unbothered! Been there, done that, dodged those bullets. I often cruise through the travel experience like a boss bitch.

Except that's not true at all. No matter how often you're on the road or how many places you've been in the world, there's so many variables that go into the travel experience that you're going to fuck it up royally from time to time. And yes, I've certainly screwed it up quite a bit over the years.

Often when I talk to people about travel and why they don't do it more often, I hear a lot about fear. Fear that they're going to make a mistake. Fear that they're going to make a poor choice or forget something. Fear that they're going to be taken advantage of or fall victim to a crime.

And honestly? I get it.

Fear can be healthy because it makes you more cautious and observant. It's nature's way of making sure you always have a version of your mother's concerned voice in your head. But on the other hand, fear shouldn't be debilitating or prevent you from experiencing the world and all it has to offer. But too often people do find themselves paralyzed with fear over the "what ifs".

With my goal to motivate more people to go out and experience the world, I decided to start a new series here on the blog which, as you can see from the title above, will be called "The Travel Fuck Up." Posts in this series will detail some of the more embarrassing, silly, or even dangerous mistakes I've made while traveling around the world. While hearing stories about someone blundering across the globe is surely entertaining, that's not the only goal I have with this serious. I want to detail how I messed up, how I fixed the problem in the moment, and any strategies I've employed as a travelers since to avoid making similar mistakes in the future.

I really hope sharing some of these stories (many of which I've never told anyone) make you laugh a bit, but at the same time also helps you realize that bad things while happen to you while you're traveling but you'll will survive them, ending up smarter and wiser on the other end of the experience.


So with that introduction out of the way, let's make our way into our very first edition of "The Travel Fuck Up" .....

Picture it - San Diego, 2012!

A wonderfully sunny day. I'd spent that morning strolling along the waterfront enjoying the sunshine on my skin and the ample brunch options dotting the shoreline near my hotel before checking out of my hotel and hopping into one of the cabs waiting outside. Some friendly small talk with the driver while darting through the very light mid-afternoon San Diego traffic before I found myself walking into the commuter terminal (now vacated, RIP) at the airport.

Confident, bold, and in control.

Two agents, both smiling, awaited me at the check-in counter with absolutely no other passengers ahead of me. Little did I know at the time that having an empty check-in area would end up being a good thing, as two of us were about to have some deep discussions.....

I sauntered up to the counter, said hello, and handed my driver's license over to the agent. She clicks away for a few seconds on her computer before asking me, "Sir, which flight are you departing on today?" Not an odd question as, at the time, San Diego's commuter terminal handled numerous daily flights by United and American to and from Los Angeles. I assumed she didn't see my name on the next departure to Los Angeles (where I would be connecting onward to Chicago) and wanted to narrow down which of the flights later today I was on. I relayed to her which flight I thought I was leaving on after which she spend another few minutes furiously typing into her computer with a big furrowed brow. While I probably should have started to get worried, being an "expert traveler" I found myself getting slightly annoyed instead.

What was taking her so long? Was she incompetent? Was she new? I had felt a bit of exasperation creeping into my face but remained calm and patiently waited for her to finish.

"Mr. Scherer? I've checked that flight four times and I've checked every other flight today leaving for Los Angeles. You're not on any of them."

At this point I still wasn't worried. Clearly she was wrong. I knew I was flying home today and she had to be making a mistake somewhere. I vacillated between annoyed and angry, managing to reply with enough decorum to remain polite - "Can you check again? I'm sure there's been a mistake."

This time it was the agent that had to hide her annoyance, and based on the fact that I can tell you about it, you can surmise that she didn't do a very good job. "Sir, I'm 100% confident that you're not on any of the flights today. Do you have a confirmation number I can look up?"

Huff. Puff. Pursed lips. My trifecta complete, I dug into my pocket to pull out my cellphone. I open up my confirmation email and triumphantly handed it over to her. "It's all right there, ma'am."

It took her all of two seconds of glancing down at my reservation before she looked back up at me with, bless her heart, zero attitude and said, "Sir, your flight is tomorrow."

I reached for my phone, my face a shattered shambles of emotion, and glanced down at the reservation. Yup. Tomorrow. Not today. Not this afternoon. Not even this evening. Tomorrow. How did this happen?

I honestly didn't know where, when, or how the error was made, but there I was. Somewhere between booking my ticket and taking this trip, I got it in my head that I was staying for one day less than I had actually booked. This little mix up meant that it was now mid-afternoon on a Sunday afternoon in San Diego where I had no plane ticket back to Chicago and no place to stay for the evening. And that's when the fingers of panic started to clutch my heart.

"Sir, how can I help?" The agent's voice drifted into my ears, pulling my attention away from the fear though it lingered in the back of my stomach.

I asked if there was any way I could change my reservation to get home today. She clicked into her terminal for a bit before coming back and telling me it was possible, but it would cost me $600. That's a no-go from the start. I'm not living on the edge of poverty but I'm also not a very wealthy man, and $600 for an airplane ticket change fee just wasn't in the budget. I politely declined, thanked her for being so patient with me and for being kind to me even though I had clearly gotten annoyed with her. I asked for a little time to think about my options in private. She kindly obliged my request with a smile.

I wandered away from the check-in counters to a row of seats in a nearby walkway, rolled my suitcase to a stop, and put my head in my hands. What to do, what to do? How could I have been so careless? Where was I going to stay tonight? The fear and frustration was back and threatening to take over. I took a few deep breaths, reminded myself that I was a grown ass man who had handled worse than this before, and attempted to calmly and clearly outline my options.

As far as I could tell, I really only had two options:

  1. Search for and purchase a last minute ticket on another airline.

  2. Find a hotel for the night and take my original flight the next day.

How do I figure out which option is best for me and how do I avoid making this mistake again in the future?


I decided that either option would work for me equally well, so it really came down to figuring out which would end up costing me less money. Cash was the key factor in this solution. This meant I needed to quickly shop for airfare and hotel costs to do a comparison of the two. I decided to start with airfare.

There are seemingly endless ways you can search for airfare on the internet these days - Expedia, Orbitz, ITA Software .... the list goes on and on. I tend to find the best results using a mix of Google Flights, Kayak, and ITA Software at the moment, though people have their own favorites that are likely to work just as well in most situations. Using my iPhone, I hopped onto to the internet and started doing some searches for one way tickets out of San Diego to Chicago leaving any time that day. One thing to keep in mind when looking at airfare is that there are some airlines that do not allow their fares to be displayed on websites other than their own. Southwest Airlines is probably the most important carrier to remember when it comes to this situation, so you should always do an independent look at Southwest's website to see what price they're offering.

As a quick sidebar, I'd also like to mention that Southwest's decision to show their fares on their own website only makes it difficult to comparison shop their flights against other carriers. There's no way to search your dates and see their price listed along side their competitors. I've spoken with quite a few people who still buy into the idea that Southwest is THE airline to look at when looking for a cheap flight, but that's often not the case at all. In many situations Southwest is pricing exactly the same as competitors such as American, United, and Delta or even pricing flights well above those carriers. If you're traveling with luggage, Southwest's "bags fly free" policy can tip the scale in their favor, but I would strongly emphasize that you need to look at what other airlines are offering and do a solid analysis before making your one and only stop when shopping for domestic airfare.

Whether you're using a web browser or one of the various mobile apps on a smartphone (Expedia, Kayak, ITA Software, Priceline, and Orbitz all offer mobile apps), it's always a good idea to know where you can turn to for flight information, especially in an emergency situation like I had found myself.

After a few minutes of searching, I came back knowing that purchasing a ticket today was going to cost me at least $320-ish dollars and get me back past midnight. Not looking too good so far. Time to look at my hotel options.....

Similar to airfare, aggregator sites can be quite useful when you need to get a hotel on the fly, though there are a few additional tools that I tend to find useful when trying to secure a cheap hotel that I want to highlight here.

Hotel Tonight is a unique travel app that I keep on my phone for those "just in case" situations like the one I found myself embroiled in. While you can use it to book hotels in general, their main selling point is that they specialize in securing discounted hotel rooms, you guessed it, that very night. This is an ideal app for someone who's on the go and finds themselves stranded in a city without a hotel room for the evening.

The app offers hotel deal access to just about every major US city and has also started to expand and offer international cities such as Paris, Sydney, and the three largest Canadian cities.

As an example of what the app can offer, here's the price for the Adolphus hotel in Dallas, TX as offered by Kayak compared with the rate being offered by Hotel Tonight's app for a booking last night. $389 on Kayak vs. $199 on Hotel Tonight. A nice chunk of change saved!

Hotel Tonight doesn't offer only luxury hotel deals though. You're just as likely to find the Holiday Inn Express next to the airport as you are a five star offering in the heart of a city's downtown core. It's a good tool to keep on your phone for emergency situations. But, just like Southwest Airlines, don't rely on them to offer you the best deal. Always look for options through traditional booking methods at the same time to confirm you're getting a good deal.

Another tool I use when trying to nail down a good hotel deal is the one-two punch of Priceline's "Name Your Own Price" tool and the BetterBidding website. While most people are familiar with Priceline's bidding tool (where you tell the site how much you're willing to pay and consequently blindly bid on and accept any hotel that is willing to accept the offer), I'm not sure every one is as familiar with the website which serves as an excellent companion to the Priceline.

The downside to Priceline's bidding tool is that you're going in blind and don't really know what you're going to get. You tell them how much you're willing to pay for a certain quality of hotel in a specific area and if any hotel is willing to accept the bid - you're booked, charged, and confirmed without ever being given the option to say no. You can save a bit of money but you give up the freedom of saying, "No, thank you." The fear of the unknown (and addiction to hotel points and status) drives many people folks running in the opposite direction, but BetterBidding aims to reduce much of that fear. The website offers:

  • Historical winning bid data for just about any major city in the world. This helps you to figure out what price point is a likely winner for your desired city without causing you to bid too high.

  • A list of hotels in each star category in the zones of your bidding city. This means that if you're using the bidding tool to find a 4 or 5 star hotel in a specific neighborhood, you can have a better idea of the potential locations you could win. It even includes a list of amenities for each property, which you can use on the Hotwire website (which features no bidding tool but does offer discount hotels blindly) to often times identify the exact property being offered.

There's even a tool that you can use that will walk you step by step through the process of bidding on a hotel in a specific city that will maximize your chances of getting a hotel of the quality level you desire at a price point you're willing to accept.

While useful, I have to admit that the interface for the website leaves A LOT to be desire. It's not particularly user-friendly and often times it can be hard to figure out where you need to go to get the information you want. When I use the website, I almost exclusively look at the historical winning bid information to get a baseline for the area I want to stay. I've happily won stays at many nice properties across the globe for much less than I would have paid booking a stay outright using this methodology, and it works particularly well in an emergency hotel situation like I found myself in that sunny Sunday afternoon in San Diego.

And again, just like Southwest Airlines and Hotel Tonight, don't rely solely on Priceline to secure your hotel. Traditional hotel search methodologies can turn up some really good hotel deals with little effort. Also, bidding on a hotel is not always the best choice you can make. I've often seen Priceline refuse to give a hotel at a price point that actually exceeds the advertised cost of hotels in a similar star ranking but aren't participating in the bidding tool.

Be vigilant and make smart choices and don't assume that just because you're bidding you're getting a good deal. You might be able to save yourself $10 by bidding for the hotel on Priceline, but you have to place a value on your time and often time it's worth paying the extra $10 to save yourself the hassle of figuring out how to get something that's already a good deal for even less. Don't let saving a few bucks force you to waste your time.

For today's clusterfuck in San Diego, the Priceline/BetterBidding combo ended up saving the day. I was able to see that I was likely to secure a hotel in San Diego for about $80 for the night, and sure enough I placed my bid and came back with a confirmation for a one night stay at the Sheraton San Diego Marina, a four star hotel being sold on other websites at $160ish for the evening.

I marched back up to the American check-in desk and again thanked the agent for working with me. I told her I'd be back for my flight on the correct day and she let me know she would see me tomorrow. Frazzled and quite stressed from the entire ordeal, I hopped outside and jumped into a cab. As we pulled out of the airport's driveway he asked me what hotel I was going to and when I said the Sheraton San Diego Marina, he turned to me and said, "Are you kidding me? I've been waiting here for a fare for over an hour and you're going to the Sheraton Marina?"

Turns out in my haste to get to the hotel, I didn't bother looking it up at all. It was across the street from the airport. Literally across the street.

The mistakes keep coming!

Instead of just hopping into a cab I should have taken the time to look at the hotel's website to see how close it was to the airport, in which case I could have seen that they offer a free shuttle to the property from the airport. I felt horrible that this cab driver had waited over an hour for a fare only to find out I was going less than 2 minutes away. At this point I just needed to bite the bullet so I ended up apologizing profusely to him and giving him a $20 tip. We ended on good terms.

I checked into the hotel and made my way up to my room. Sitting right on the marina, my room was high up and featured a balcony looking out over the water. I plopped myself down out there, took a deep breath, and tried to regroup. I'd fixed the problem, but how do I make sure I don't make this mistake again?

I realized I had let my hubris as a "seasoned" traveler stop me from taking some basic precautions when planning my trips. I was so confident in my own memory and "mastery" of the travel arena that I never bothered to collect all my trip information into a single location where I could confirm I had all my bases covered. One little travel calendar would have been all I needed to see that I had booked two nights worth of hotels on a three day trip. But I didn't keep one of those because I thought my crackerjack mind was enough. Clearly it wasn't.

Things changed after that day. I now use one of the travel world's most popular applications to keep all of my travel itinerary information for me - TripIt.

TripIt works by taking all of your travel confirmations and information and consolidating it all into a single location. You can store the information for your hotel bookings, plane tickets, and even something like a day tour booking in the app which will then be displayed to you as a running itinerary detailing everything on the trip. You can easily see that you forgot to book a hotel or didn't get a return flight on the trip by opening up the app and clicking on any of your trips. It's simple to read and clearly laid out in an organized manner, making it an excellent place to confirm you're good to go.

It even stores confirmation numbers for your activities, so it's the perfect replacement to your giant stack of printed confirmations.

Whenever I am planning a trip and think I have it "completed", I always open up the trip documents in the app and walk myself through the trip line by line to make sure nothing is missing. I've actually discovered I had gaps in hotels/flight itineraries on three other occasions since the San Diego debacle thanks to this app.

But you don't need an app like TripIt to keep your organized if you're not traveling all that often. Something as simple as writing it all down in your calendar or on a piece of paper will suffice. The key is to avoid silly mistakes like the one I made in San Diego by taking a few precautions to ensure you're covering all your bases. As the Russians say, "Trust but verify."


Well, that concludes the first edition of "The Travel Fuck Up." I hope you found it interesting and maybe learned a thing or two about how to think on your feet while traveling and some tools you can use to make the travel experience a little less scary. As I said at the beginning, so many people avoid travel because of all the things that could go wrong. It's important to get past that fear by realizing that despite the fact that something will inevitably go wrong, if you're prepared and flexible you can manage the situation just fine.

Till next time....!


Country Count: 70/193

Hello! I'm David - world traveler, food aficionado, gay dude, and storyteller.  This is where I share amazing sights, delicious dishes, LGBT travel advice, & my favorite stories!


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