As important as things like loyalty programs and credit cards are to gain upgrades and status and other luxury perks, sometimes it's the simple things that get overlooked that leave you out in the cold.
In this post we'll look at some things to remember leading up to your trip and on the day of your trip that will help your chances of a getting a better experience.
None of the below are guaranteed to be successful-- again, the best way to increase your chance of an upgraded experience is to hold status with an airline or hotel.
Things to Remember
Dress nicely: Airlines want first class passengers to look expensive. Paid passengers don't want to spend first class money to sit with scrubby looking people. It sounds harsh, and it's not about the airlines' view of you as much as how they think their paid passengers view you. First class is the airline's "front porch" and they want to put their best foot forward. Wear a nice pair of jeans or slacks instead of sweatpants. You don't have to be Harvey Specter, but you should look presentable.
Harvey probably gets upgrades all the time .
Be nice: If you're an asshole and don't have status, no one will give you the time of day. You don't matter. But if you're nice and patient, especially if the agent is taking shit left and right, they may reward you just for being nice. A smile can go a long way for these employees. Do not expect anything if you do not have status though as Gate/Front Desk Agents are very limited in what they can do.
Pick flight times wisely: Think of it like a restaurant reservation- if you just walk into a hot restaurant at 8pm on a Saturday, don't expect to go right on through or to get any extra attention. If you travel at off peak times you are more likely to find an agent that has open first class seats that may be generous. If you're flying during peak times like 7-9am or 4-6pm, there will not be any first class seats for a non-status holder. Don't even try. Remember, business travelers generally fly on Monday morning and Thursday evening. Vacationers usually fly on Fridays and Sundays. If you are upgrade-eligible, you are competing with a bunch of other people that probably have higher status than you. You want to limit the competition.
Travel during off-peak times: Similar to the above, don't expect a hotel upgrade if you're staying at Disney Land in the summer when every family with kids is going. Same with going to Mexico during spring break. Be smart. Think about when kids are in school-- that's your golden travel period. Hotels will be emptier, increasing your likelihood of scoring an upgrade.
Ask for an upgrade: All they can say is no! You'd be surprised how often (more at hotels than on planes) you can grab an upgrade just for asking. If a hotel has a bunch of suites open, they have nothing to lose by giving you a suite, and they build up goodwill by giving you a more memorable experience. This does not work the same way on airlines!
Confirm your reservation: You should always confirm your flight, hotel and rental car three times- one week before, the day before, and the day of. You don't want to get to the airport an hour before your flight and realize you booked your flight in the wrong direction.
Get on Twitter: Twitter is the best tool for travel. Instead of calling a hotel or airline when there's a problem, tweet them and you will get a much quicker answer and someone much more likely to help.
Start a dialogue with your hotel: I always call or email the hotel after I book a stay. I do this to first of all confirm my booking. Also, I use it as an opportunity to get my preferences down and ask for upgrades. I do this even when I'm staying somewhere I don't have status, because usually they will put it in the notes. Remember to take down the name of who you spoke with. When you check in you can reference this.
Decide what you're willing to pay for: Generally when you travel you'll need to make some compromises. For me, an aisle seat is crucial and I will gladly pay $15-20 more to get an aisle seat if I have to, especially on longer flights.
Sign up for Global Entry: Global entry is a government sponsored travel program that allows you membership in TSA Precheck. You'll need to fill out a detailed application, they will run a background check and you'll need to go in for a quick interview. It's absolutely worth the $100, and a few premium credit cards offer a statement credit for it. Having Precheck is incredibly valuable despite its limitations, and Global Entry allows you to bypass customs when you return from international travel.
Are any of these ten tips guaranteed to get you what you want? Of course not. My goal here is to put you in the best possible position to be able to take advantage of an opportunity.
Don't forget the little things. You don't want something small preventing you from a better experience.