1. Not bringing enough small bills or change.
If you're sticking to the beaten path, you can usually run to an ATM if you fail to bring enough cash, but that won’t help when you need smaller bills or coins. There’s always tipping, tolls, cab fares, and laundry services to consider. Splitting costs in a car full of people also gets complicated fast when nobody remembered to bring anything smaller than a $20. (Side note—as someone with retail experience, I promise no cashier has ever wanted to break that $100 bill into your preferred combination of $5’s, $1’s, and quarters with your purchase of a pack of gum, either.)
2. Assuming the weather reports are accurate.
I have packed a suitcase full of the wrong clothes more than once because I based my choices solely on weather reports. Always opt for that one jacket, pair of long pants, pair of shorts, or umbrella that you don't think you'll need. Otherwise you may wind up miserable or on an unplanned shopping spree.
Just because you have extra space doesn’t mean you should fill it. There was a time for me when going to a show in a car automatically meant packing a camping chair and a cooler. I’m not saying those things are never worth the space—for some people, they are. But if you’re like me and you wind up not even using the cooler and being angry you have to keep up with a chair, just save yourself the trouble and don’t bring it in the first place. One time I accidentally packed my medium sized suitcase instead of the carry on size. It fit in the car just fine, but I had to lug that thing around for a month. I dragged it around uneven city sidewalks, down narrow hallways, and at my lowest moment, up 5 flights of stairs in NYC. I came home with some newly impressive muscles, at least. Never again.
4. Not taking the time to print electronic tickets and itineraries in advance.
This one is my tragic flaw. I know most people love traditional hard copy mailed tickets for the souvenir factor, but I am in love with e-tickets. They’re usually cheaper because you don’t have to pay for shipping, and you can lose them 37 times and just reprint them the day before the trip if you need to. Until you can’t, because it’s 3 am, your flight leaves in 4 hours, and you just realized your printer is out of ink. I did this to myself last fall. Three months later, I traveled to Jamaica without printing my flight itinerary because I knew I could just print my boarding passes at the airport. That plan worked out fine until the travel agency wanted my return flight information before putting me on a bus to the resort, and “Let me just pull up my email confirmation” isn’t really an option when you're out of the country and there’s no wi-fi. Save yourself the hassle and have all of your tickets, flight information, and hotel confirmation numbers on paper in one place before the trip, just in case.
5. Traveling domestically without a passport.
Obviously you don’t need a passport to travel in your home country, but if you already have one, take it with you. You never know when something might come up to make you glad you had it. A friend of mine had a canceled flight once and the only route that would get her back home the same day had a layover in Canada. She was able to take that flight and avoid being stranded overnight because she had her passport on her, even though her original trip was only in the United States. There was also a tour one year where an unexpected opportunity came up for my friend and I to continue on to the last two shows that happened to be in Canada after our planned east coast run. We had to go back home instead because guess which one of us didn’t bring a passport? Lesson learned.
6. Not reading ticket and reservation details before clicking “purchase.”
If you’re a regular concert ticket buyer, then you know the adrenaline rush that accompanies the moment tickets go on sale. Being too slow to buy can mean the difference between front row and the nosebleeds or missing out on a ticket altogether. But that adrenaline rush can make you do stupid, stupid things, my friends. Stop and read the details once you've got it in your cart.
I had a “Spring Awakening” phase back in 2008. If you're not familiar, it's a play with a pretty neat setup that allows 26 audience members to sit directly on stage mixed in with the actors. When I managed to snag one of the coveted and impossibly hard to get stage tickets, I jumped at the chance to buy it. I had planned to go to the showing in Tampa because it was the closest show to me that hadn't gone on sale yet. I was on cloud 9 after my purchase right up until the moment I finally read the word “Broadway” in the confirmation and realized I had bought myself a ticket to the Broadway showing in New York City instead of the tour version of the show in Tampa. In my moment of excitement I had clicked the wrong ticket link and failed to read the details before completing my purchase. As a result, I got stuck with an expensive ticket I couldn’t use, and to add to my fail, the Tampa on stage seating was sold out by the time I finally figured out what I had done eight hours later. Thankfully, having an extra front row stage ticket made for a pretty easy sale, but not every mistake ends in an easy fix. (In the end, I wound up with stage tickets to two showings in Cleveland because yes, I’m that person that tries to buy a ticket to Florida, accidentally gets one to New York, and actually winds up in Ohio).
7. Not double checking GPS travel routes.
Because the "unexpected beautiful" you find might turn out to be Lake Tahoe when you meant to be at Yosemite.
8. Traveling without a cushion.
Of money, that is. I love saving money and whittling down my travel costs to the bare minimum, but I know it would be irresponsible and dangerous to go without having extra money in my account for emergency situations. Be prepared for the moment your tire blows out or your suitcase gets lost. Once over the course of a month long roadtrip, I had to replace windshield wipers, a headlight, a turn signal, and TWO GPSs. That same trip, a week of the tour got canceled and we found ourselves with no place to go for a week where we had planned out free places to stay in advance. Luckily, we had a friend in the area that we were able to crash with, but that could have easily been a week's worth of unexpected hotel fees.
9. Not knowing how to work your new camera in advance.
I went to Niagara Falls and took the most gorgeous pictures...in 640x480 resolution. They make for some really high quality thumbnails. #NiagaraFails
10. Don't pack toy guns if you're traveling out of the country.
Because the Jamaican customs form categorizes them under "traveling with firearms," and that is one box you do not want to have to check "yes" because they're already in your checked luggage. I laughed at the situation, but the customs worker was not amused by me and my colorful squirt guns that had to be confiscated. Or maybe the lesson here is don't check "yes" next to the firearms box just because you have tiny plastic water guns in your bag.
What are some of your travel regrets?