How I Book Travel

I’m far from an expert on booking travel, and I hope I hear from tips and tricks that I don’t know from readers of this blog, but I DO travel quite a bit and have knack for being just a little more creative than most travelers and spending just a little more time exploring all options than most travelers. So for what it’s worth, he’s my basic strategy for attacking travel planning:


Traditionally, it’s cheaper to fly on Tuesdays, Wednesdays and Saturdays, and most expensive to fly on Fridays and Sundays. Prices change by the minute, so if you find a fare that’s awesome, book it. Tuesdays and Wednesdays, particularly late at night, are good times to book, as many airlines launch their sales then. When you’re ready to start looking:

1. Search on Kayak.Com. There are a lot of airline search engine sites, and many of them are good, but I’ve always found Kayak the easiest to use and the best at ferreting out deals. Also, there’s no booking fee on Kayak. I always check the “add nearby airports” for both legs to see what alternative airports show up and the “my dates are flexible” option (even if you think your dates aren’t flexible, you might find it’s cheaper to fly in the night before or a night later). I always price both one-way and roundtrip. Roundtrip rarely saves you any money anymore, and I’m fine taking different airlines coming and going.

2. Search on Southwest.Com: As much as I “luv” Southwest, the one frustrating thing about them is that they don’t allow their fares to be included on any search engines. So you have to search on its website to compare to the Kayak results.

3. Consider alternate airports/airlines: Knowing which ones isn’t easy. That’s why I always check the “add nearby airports” button on Kayak, because it helps train me on airports that are near the major ones. I might not use them this flight, but learning which ones are out there may help me in the future. Once I find an alternate airport that I haven’t heard of, I go to the airport’s website and look for a list of airlines that serve the airport and the destinations they fly to.  Often, the airlines that serve alternate airports don’t show up on searches on Kayak or other search engines, so you have to visit their websites and check for your travel dates.

4. If you’re desperate … consider “hijacking” to get an affordable fare: An unfortunate word for sure, but the concept is booking airfare independent of each other. If an airline doesn’t fly to Las Vegas, for example, but offers cheap flights to a city where another airline DOES fly to Las Vegas, you can book the first flight, leave yourself enough time to claim baggage and check-in, etc., for the second flight. I’ve never been forced to do this, but I’ve come close a few times, especially on international flights.


By far the most research-intensive of all traveling. No one wants to be stuck in a rundown motel in a dangerous part of town, even if you’re only planning to be there a few hours.

  • Research your destination. If it’s a leisure destination, like Las Vegas, hotels will be more expensive on weekends. If it’s a business destination, you’ll find better deals on Friday and Saturday nights. This can make a big difference on when you arrive, so I always do all my research before booking airfare.
  • I think people get too caught up in “stars.” Be sure you understand what a “star” means. Sometimes, it simply means a hotel has a restaurant on-site and is not indicative at all of the true quality of the hotel. For most of my travel,  a “two star” hotel is just fine.
  • A number of hotels are now offering discounts for prepayment. You’ll save 10 bucks or so a night, but lose the flexibility of switching to another hotel if you find a cheaper rate later on. And, of course, if you have to cancel your trip, you’re out the money.

When you’re ready to start looking:

1. Search on Kayak.Com: Always the first place I start. You can reorder results to whatever is most important to you, from location to price to ratings. It gives you an instant snapshot of what the market is like for your chosen dates. If I’m a loyalty member of any of the hotels that pop up, I’ll log in to my account on the hotel’s actual website and see what my price will be. It’s usually cheaper than search engine prices.

2. Research: If it’s not a hotel I’m familiar with, I read lots of reviews. I want to know what I’m not being told on the booking sites or even the hotel’s own site. Once I feel comfortable with a choice, I also go to the hotel’s actual website and make sure it has all of the amenities I prefer and also see what surprise charges I might get (like parking, wi-fi or the dreaded “resort fee.”). If it’s just before or after a flight, I also like to see whether they have a free airport shuttle. Taking the shuttle might save me a day or two on my rental car.

3. Consider other lodging possibilities: As described on the Stay page, you don’t always have to stay in a hotel. Sometimes you can find something much bigger for as much or less than a hotel. I’ve become a huge fan of AirBnB. It’s become much more than the “couch surfing” of its initial days. If you’re staying for four nights or more, or are traveling with a group, you might be able to rent a private house or a condo on a site like Vacation Rentals By Owner for less than a hotel room of bloc of hotel rooms. Same goes for time-shares. The market for them is always in a serious glut, and owners are faced with paying for annual maintenance fees whether they go or not, so many try to rent their weeks just to cover their fees. RedWeek.Com is one website that advertises these opportunities, which are usually in resort communities with lots of amenities.

4. If you’re desperate … try the opaque sites: My wife has been successful in bidding on Hotwire.Com and similar sites. I’m not a fan of doing it often with flights or hotels, because I think travelers give up more than they get since you don’t know the actual hotel or flight details. Using a site like BetterBidding.Com helps tremendously, but it’s never a guarantee. For that reason, I only use it as a last resort when I can’t find anything reasonable through more traditional means. But if you really don’t care where you stay, and only care about price, this is a great way to get a deal. Especially on weekends when nice hotels that cater to business travelers are mostly empty and dump a lot of their inventory on opaque sites.


Cars are usually the least painful part of travel planning. Not really a lot of strategy involved.

  • I try to stretch my pickup and dropoff times to eliminate one day on the rental. I can usually pick it up an hour earlier than I say I will, and most companies give you a one-hour grace period on returns.
  • I always make sure the rental counter will be open when I want to pick the car up and return it. You’d be surprised how many aren’t open early in the morning or late at night. That’s a rude surprise after you’ve already booked your nonrefundable airfare.
  • Verify your coverage with your insurer and the credit card you use to book the car. In almost all cases, you’re almost fully covered for accidents through those two, so no reason to buy additional insurance. And I always giggle when I see the rental counter offer me a GPS for $15 a day. Folks, if your smartphone doesn’t have a GPS in it, you can buy a decent GPS unit for $50 or less.
  • Fill the tank up yourself … and bring the car back with a full tank. Don’t fall for the “prepaid option,” which usually has a deliciously low per-gallon price. You’re paying for an entire tank of gas that, unless you’re strategic enough to bring the car back bone dry, will cost you more.  Take note of gas station locations as you leave the airport so you don’t get stuck circling a strange city looking for a gas station when your flight is ready to take off.
  • Be wary of paying to use the car’s toll-road transponder. There’s a daily convenience fee for these, in addition to the tolls. And the kicker? They charge you the daily fee for the length of your rental, even if you only use the transponder just one day. Some pre-trip planning, or bringing along you own transponder, will help make you make the right decision on this for your trip.

When you’re ready to start looking:

1. Search on Kayak.Com: All my searches, including cars, start here. You may find an independent rental agency that you’ve never heard of that is cheaper than the national brands. The cars at those will likely be older and not in as good of condition, but you’ll save some money.

2. Compare those results to what you get using your loyalty companies: As I mentioned on the Drive page, I believe there’s value for some travelers in being loyal to one brand, especially from a time-saving standpoint. But I judge on a rental-by-rental basis just how valuable it is to be loyal.

3. Bid on opaque sites: While I’m not a fan of using opaque sites like Hotwire for flights or hotels, I don’t share that same disdain for cars. Since I never know the exact make and model of the car I’m getting even when I rent from a loyalty program, it doesn’t really matter what I get from an opaque site. Since you’re putting your pickup and dropoff times in, there’s no risk unlike with hotels and flights, when you can end up in a bad part of town or with an early-morning, two-stop flight.

4. If you’re desperate … do the math on taking an Uber, cab or hotel shuttle to an off-airport location. Airport locations usually add tons of taxes to rental cars (in Texas once, the taxes on my rental were three times what the rental actually cost), so if you pick up the car off site you’ll avoid those taxes. If you have time and don’t mind the hassle, you should do this all the time, at least on long rentals. And sometimes you’ll realize you don’t need a rental for your entire trip, saving you more money.


Online reviews

One of the great advantages of booking travel these days is the sheer number of online reviews available from multiple sources on the Internet. I love using these, especially for hotels, but I also have one big gripe about them – how do I know who is posting them? If my neighbor, or an old college friend or a co-worker tells me their opinions of something, I know them well enough to adjust their expectations to mine. But a random stranger? A person who routinely dines at Michelin Three-Star restaurants is probably going to be more critical of a restaurants than I am, and a person who dines weekly at McDonald’s is probably not going to be as critical as I am. But rarely do posters include the valuable “who I am” information in their posts. So I look for trends. If I see one review that says the bed is lumpy in a hotel, I dismiss it. If I see five in a row that say the same thing, I take note. That’s why I tried to lay out a “traveler’s profile” of myself on the About page. That way you know who I am, what I value and what I don’t, so you can adjust my expectations to yours.

Loyalty programs

Just like it amazes me how people toss coupons in the trash every Sunday even for things they buy every week, it amazes me how people are loathe to join as many loyalty programs as possible. Perhaps it’s because they don’t want their inbox cluttered with daily deals. But I’d suggest then that those people aren’t truly serious about finding deals anyhow. Any time I book a new hotel, or new rental car company or new airline, I join their loyalty program. Even if I never use that company enough to earn its freebies, I’ll usually get some perks right away (even if its just time-saving perks) and will always get email deals that might help with impulse or even planned travel. Also, many programs are linked to others. When I flew JetBlue, an airline that I’ll rarely fly because of its destinations, I had the points I earned transferred to my Delta account. I’ll probably never reach reward status with Delta, either, but I’m that much closer to now. Finally, these programs are almost always free, and you can sign up for them in less than two minutes.


The web is full of great resources for travel; some better than others. I prefer ones that are complete in their information, rather than the 80% of sites that are designed just to get web hits and have superficial information that is hardly helpful. As with most things, you get what you pay for. While there are some amazingly great free resources available, I recommend these three that cost a little bit of money:

USA Today newspaper: I’ve never understood why my fellow newspaper journalists were so harsh on this newspaper. After reading it every morning, I think I know something about everything that is going on in the world, whether it’s government, business, sports or entertainment. And I can also explore the Internet to learn more topics that I want to know more about. But for travelers, its Money section is pure gold. The newspaper was designed for business travelers, so it has heavy emphasis on trends in hotels, airlines, etc., and those trends are usually applicable to leisure travel as well.

Las Vegas Advisor: If you’re going to Las Vegas, even for a long weekend, it’s hard to imagine you won’t recoup the value of this $40 subscription and then some. Why? It comes with one of the best destination coupon books ever assembled. And it’s not full of those near-worthless $1-off-an-$80-show coupons that freebie books offer; it’s full of 2-for-1 one offers on meals, hotels and shows, as well as lots of other savings for things you’re probably going to do anyhow. And the monthly newsletter is full of more tips.

Leave a comment

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Blog at

%d bloggers like this: