Rules for Life

Make Your Travel More Tolerable Before You Book

Traveling is a bittersweet experience. On one hand, you get to see new places and have unique experiences, while breaking up the monotony of your normal routine. In contrast, the actual process of traveling can be absolutely soul-sucking. It’s frustrating when you take a refreshing vacation, only to have all of the stress return during the trip home. Between long lines, cramped seats and annoying people, the odds are against you having a pleasurable travel experience. Fortunately, there are hacks to make the experience much more tolerable. These tips are available in a three-part series. To help make your travel more tolerable before you book, check out Part One: Pre-Booking.

Marry an Airline

So many people will spend weeks searching for the lowest priced flight, but they’re really wasting time and money, while also losing their sanity. Pick one airline that travels to most of your preferred destinations. Sign up and enroll in their frequent flyer program, and stick with it. I prefer the Delta SkyMiles program due to their benefits and great service.

When you accumulate travel credit with one airline, they treat you better. You get to pick your seats so you’re not separated from your travel partner. The seats you get are closer to the front and roomier. Plus, you are allowed to board earlier, which means you don’t have to fight for overhead space to store your bag. They give you free food and drinks, so instead of paying for overpriced food at the airport, it’s included. Airlines don’t nickel and dime frequent fliers over things like checked bags, alcoholic beverages, extra space and priority boarding.

Many “discount” airlines charge you for every little thing. When it’s all said and done, you end up paying the same amount you would’ve paid by booking direct with your preferred airline. Build up status and you’ll start getting premium first class upgrades. Accumulate enough miles and you’ll get flights for free. I traveled to Barcelona and Athens direct and only paid taxes on the flights. That’s a $3,000 value.

*Pro tip: The best time to book a flight is roughly 55 to 70 days before scheduled departure. You get the best rates at this time.

Apparently, Tuesdays are the best days to book.

Commit to a hotel group

Take this step immediately, as this one is a no brainer. Hotels can get expensive, in the range of $400-$800 per night in premium vacation destinations. A week long vacation can cost over $3k for the hotel alone. Picking one hotel loyalty program and sticking with it will help you get points to redeem for free nights. Soon, you will have enough for an entire week, free of charge.

As you gain status with that program, you’ll get perks. Often these include complementary room upgrades, free Wi-Fi in the room, late checkout and early check in privileges. Nothing is worse than arriving at your hotel only to be told you’ll have to wait three hours for the room to be ready. Avoid this situation by staying loyal to one chain. I prefer the Starwood-Marriott-Ritz program due to the quality of their hotels and the number of hotels they offer across the world.

Tie in your credit card

The best way to multiply airline miles or hotel points is by using a credit card that ties into specific loyalty programs. They literally give you free points and miles for using their card. On top of that, they package in other benefits like free companion flight certificates, free nights, automatic higher status, and discounts. Plus, they generally offer a very generous sign up bonus equivalent to $700 – $1,000.

I use the Delta Platinum SkyMiles AMEX and the Starwood AMEX. If you’re not tying into a specific chain’s loyalty program, the Chase Sapphire Reserve is an excellent card that gives you 3x points on travel and dining. You can redeem those points for travel on a 1.5:1 ratio, which is a huge bonus. Additionally, you have more freedom for redemption, as the card doesn’t lock you into specific brands for hotels, flights, and rental cars.

*Pro tip: For the best deals in hotel loyalty programs, frequent flier programs and credit card rewards programs, check out The Points Guy. His site provides people with the latest and greatest ways to maximize your credit card’s travel program.


Anyone opposed to having their fingerprints and retina captured should skip this part. For those not concerned about a “Minority Report” situation, make an appointment with CLEAR. You’ll have to pay a fee and go through a screening to sign up. This service allows you to cut the entire security line, saving you tons of time during the check in process. I’ve had situations where I pulled up to the airport in a taxi and got to my gate in under ten minutes. You will get much more time back, so you don’t have to worry about giving yourself three hours to get to the airport. Frequent travelers absolutely need CLEAR.

TSA Pre Check & Global Entry

Freaked out by CLEAR’s technology? The next best thing is enrolling in TSA pre-check for domestic travel, and Global Entry for international. Both services validate that you’re not a terrorist or a drug smuggler, while allowing you to pass through security and customs lines relatively quickly. This is a huge time saver, and helps you avoid taking off your shoes and taking out your laptop before boarding.

Check Out Making Travel Tolerable Part 2:  Preparing for your Trip