CFI Blog

21 Tips and Tricks I Use to Evaluate Travel Options

“The traveler was active; he went strenuously in search of people, of adventure, of experience. The tourist is passive; he expects interesting things to happen to him. He goes ‘sight-seeing’.”
– Daniel J. Boorstin

Daniel J. Boorstin

My wife and I love to travel. It’s one of the highest priorities in our lives, and while not enough to make us want to eschew accelerating retirement as much as possible just for a life of vagabonding, we do take one longer trip per year, preferably to an international location.

Just because we like to travel doesn’t mean that we like to pay more money than anyone else for it. I’ve found that, depending on where we go, our expenses usually line up in this order:

  1. Transportation to get to and from a destination
  2. Lodging at the destination
  3. Food
  4. Activities
  5. Everything else

Since my wife can only take off one week at a time, aside from the one exceptional circumstance of going to the World Cup in 2010, we usually have to limit our trips to one destination, or a couple of cities that aren’t far from each other and are easy to get from one to the other.

Also, since we don’t have that much time in a given destination, we can’t rent an apartment or a house where we’re going, except for circumstances that I’ll describe below. If we were going to stay in a place for one or two months, we’d definitely try to rent an apartment during that time to reduce the daily cost of lodging.

I’m personally of the opinion that my lodging is only a place for me to put my head on the pillow at night and clean up in the morning and to store my belongings while I explore and undertake activities. I’ve stayed at hostels as a thirtysomething in both Cape Town, South Africa and London, England, so I am not averse to more rustic accommodations; however, my wife at least wants the following (fairly reasonable) list of requirements met for what she stays:

  • Safe
  • Private
  • Quiet
  • Reasonably comfortable, meaning no sleeping on mats on the floor or a bed mattress stuffed with feathers

With that minimal list of requirements in mind, let’s look at how I search for travel deals when I book our vacations.

Places I search when exploring travel options

I’ll be the first to admit that I’m not Chris Guillebeau, the ultimate travel hacker. Even though we travel a lot, I use a 1% cash back rewards card for my credit card usage because, to me, the cash in hand (what little there is) is worth more than mileage points. If you’re looking for rewards cards to travel hack with, you can check out my interview with the PT Money rewards cards gurus. I’m a reasonably accomplished searcher, but I’m not going to spend hours looking for $10 less on a flight or weeks using credit card hacks to try to get miles. Since I don’t have debt, I’m happy to sign up for the free cards that they offer at the airport that give you a free flight if you spend $X in the first year, but beyond that, I’m not going to put in incremental effort for travel hacking.

So, think of this as “travel hacking lite.”




One of my favorite websites to use for getting ideas of where to go is SkyScanner. The function that makes SkyScanner so interesting to me is picking an airport and dates and checking everywhere in the world.

The results interface is a little klunky, and for many locations, they haven’t had a price checked in recent history, so there are no results, but it at least gives you an idea of what destinations might be within your price range.

You do have to go a couple of layers deep to actually get to the flight searches; one issue that I have with them is that you can’t eliminate airlines from the initial search. If I don’t want to see the rates for Crashalot Airways, then I have to drill down to a specific city before I can uncheck that option. But, for a first blush at prices to expect as you’re looking at destinations, this is a great site.



I like to go to Kayak next because they compile almost all of the airways I fly with or would use, with the exception of Southwest. Their interface is easier to work with than SkyScanner’s, and I rarely find a deal outside of Kayak that is cheaper. They also have flexible date options, which is useful, although they don’t have the ability to easily search from, for example, 5:00 PM on Friday through noon on Saturday. They also have recently added tabs for hotels and cars so you can see options without leaving their site. More on the hotels search later.

Priceline and Hotwire

Sometimes, when we’re flexible enough with flying, we can use Priceline and Hotwire. I used to use Priceline all of the time when I was dating my wife and she lived in Fort Worth while I lived in Fort Knox (they’re both Forts, so they should be close, right?). I knew the exact price to go from Louisville to Fort Worth on a weekend and knew what flight I’d get every time.

If we’re flying somewhere unfamiliar, then we will want to arrive while the sun is still up so we can get our bearings. That eliminates Priceline and Hotwire as options. Also, if we’re doing a quicker trip, like a four day weekend, we don’t want to get a super late flight in and a super early flight back, so we won’t use those options. If we’re flexible, though, and don’t care what time we depart or return, we’ll take a look at both of these to see if there are better options.

The airlines

The airlines

I’ll take a quick cruise through the airline websites of a handful of airlines that I would like to fly to see if I can get a better deal than what Kayak is showing me. If they’re the same as what Kayak offers, then I make sure to go back to Kayak so that they get the credit for showing me the fares; they did the work, and they deserve the reward.

I am also signed up for the airfare alerts for several airlines.

Also, I am signed up for every frequent flier program I’m aware of. Even though I try to consolidate my miles on a few airlines – usually the keystone partners of the travel alliances – I want to make sure that I get credit for whatever airline I fly on. When we lived in Virginia and had family in Georgia and Texas, we’d usually travel enough that we’d get one free flight per year, though those are getting a little harder to come by than they used to be.


Chile once required a visa, and you could pay for it upon arrival. Costa Rica requires an exit fee. Most countries, at least for U.S. citizens, do not require visas. It is wise, though, to go to Google and search for the term “U.S. traveler visa requirements for [DESTINATION COUNTRY HERE]” if you’re traveling internationally. Sometimes, the information is slightly out of date, although the Department of State will have the most recent visa requirements. For example, everything we saw said that Chile only accepted cash for the visa. When we arrived, they rejected half of the cash that we had brought because it apparently wasn’t new and crisp enough, but then they pointed us to the credit card symbol, so we paid for the second visa with Visa.

Scott’s Cheap Flights

I signed up for the e-mail notification service at Scott’s Cheap Flights (#aff) a few months ago, and we’ve already booked a trip for my wife, me, and a friend of ours to go to Warsaw and Krakow, Poland. Founded in a Denver coffee shop, Scott’s Cheap Flights now employs 25 people who hand scour the web for travel deals. Almost all of the deals are to international destinations, and most of them are at prices that are cheaper than I usually see. Besides buying a trip to Poland through them, we’ve been tempted by trips to Peru and Costa Rica as well. You can get the free e-mail, or they have a premium service that weeds out the really good deals. You do need to have some flexibility to travel, but it never hurts to take a peek and see if the deals match up with your availability.

World Nomads

We use World Nomads travel insurance (#aff) every time we travel internationally. Fortunately, we’ve never had to actually use the insurance, but you don’t buy insurance because you want it to pay out. You buy insurance for the catastrophic cases where you need it to pay out. If we’re in Poland and I try to pull a Fred Sanford and tell Elizabeth that this is the big one, we probably don’t want me to be stuck in a Polish hospital for weeks on end. Travel insurance will pay for medical evacuation. The same applies if there’s a political uprising and you don’t want to hang around to see who wins. Travel insurance will pay for the evacuation.



Since I already have the Kayak page open, I check out the hotel options for my destination.

Their idea of relevance is foreign to me, so I suspect it’s “pays the highest finder’s fee to Kayak.” Make sure that you use the filters on the left hand side and sort by Price – low to high.

This is search I use to set my baseline for how much I’ll pay for a hotel. I might not get a hotel, but this at least gives me an idea of a rough budget for my trip.

This is the next place I look to see if they can beat the Kayak prices. About 1 in 4 times, I can find a cheaper price off of for the same hotel as I can on Kayak. The filtering functionality is irritating, as each time you add a condition (e.g. maximum price for a room or number of stars), the page reloads, so if you get anxious, like I do, and make multiple changes at once, they’ll often get lost as the site updates.

Note, when I was writing this article, their filters weren’t working at all. You can see it in the yellow highlights with the circle next to each filter. Another strike against



We’ve used Vacation Rental By Owner many times, both domestically and internationally, and have been pleased about 90% of the time. In most of the VRBOs you would rent, you’re getting them for the convenience and for a kitchen to use while you’re there. When we went to the French Riviera, we stayed in a VRBO in downtown Menton, France, and were very happy with it. It was pretty basic, but very convenient. We shopped at the local store for breakfast and lunch food (yes, it’s cheaper to go out to eat for lunch rather than for dinner if you’re trying to save money, but, hey, it was our 10th anniversary and we lived a little!) and for cheap, delicious bottles of wine.

The website is sometimes hard to navigate. It’s fine for getting you into a specific town, but you cannot sort by price or narrow down geographically (e.g. 1 mile from San Telmo in Buenos Aires). Additionally, as best I can tell, the owners get to moderate the comments left about their properties, so they cherry-pick the best. We left a mediocre review on a house in Atlantic City, New Jersey and it never appeared on the website. That would never happen with some of the other websites.

Also, just be aware that this is not a hotel. You’ll probably have to leave the place in the same condition that you found it. Some owners have a cleaning fee built in and some don’t. Just make sure that you read the terms and conditions before renting.


TripAdvisor is a great multi-purpose website that we use for looking, for the purposes of lodging, at bed and breakfasts and smaller, boutique hotels that might not otherwise show up on our searches.

We also use TripAdvisor as a secondary source for the quality of hotels that we find on other websites. I’ll cover more of TripAdvisor’s uses later.


I’ve never used Airbnb before, so I can’t vouch for my personal experience, although I do check it to see if there’s a place that might be viable for us to stay in. So far, no luck, but that won’t keep me from looking. I think this would be a good option (though, I don’t know how it would compare to CouchSurfing…thoughts?) particularly if you’d like to stay with a local and perhaps get guidance on some good places to eat or drink or dance the night away where you won’t see other tourists.

Again, I’m not happy that you can’t sort, but you can at least put filters in to narrow down your choices.

I do like that you can zoom in on an area on the map and narrow down your choices that way.


Once you’ve decided where you’re going to go and where you’re going to stay, you need to figure out some things to do. We usually don’t like to have much down time – maybe one day where we don’t really plan on doing anything but sitting in a bar or café or restaurant and reading or people watching. If we wanted to sit around and do nothing, we figure we can do that at home. For us, traveling is for experiences and for meeting people.



I really like using TripAdvisor to get a sense of what’s really worth going to see and what’s worth spending our time on when we arrive at a destination. I’m very leery of the over-touristed tourist traps that are more hype than anything. TripAdvisor has plenty of recommendations, so it’s a crowdsourced version of what to do. Sometimes tourist attractions are popular because they’re so good, and this is a good way of sorting out what’s worth seeing and what’s not.

We’ve also used TripAdvisor to find good restaurants when we’re traveling internationally. To us, it’s not as good for domestic restaurants.


Yelp doesn’t have very many international locations, so its use when you’re outside of the United States is limited.

However, when we’re traveling in the United States, it’s our go-to tool for places to eat and to validate the activities that we’ve found on TripAdvisor. We use it primarily for restaurants, as it seems to be the best crowdsourced dining out guide that we’ve found. We’ll also use it in conjunction with to see if we can find gift certificates for the good places.


I’ve always liked the Frommers guides as a reference, although when traveling, I’ve taken the Lonely Planet book and simply torn out the applicable pages for whatever I was doing for the day so that I wasn’t that tourist carrying around a huge guidebook and keeping my nose plunged in it all day long. I’m getting to the point where a white t-shirt, shorts, and pulled up black socks are starting to look attractive.

What I like best about Frommers is their suggested itineraries. That gives me a good idea of how long I should plan for each place. When we were younger, we accelerated the itineraries, and now that we’re getting older, we like to go a little slower than the itineraries suggest.

We rarely stay in the places they suggest or eat in the restaurants they suggest unless they’re verified by one of the other sources listed above. We’ve found that we can get better value for our money if we search a little more on our own for places.

Amateur Traveler

Amateur Traveler

I enjoy listening to Chris Christensen’s Amateur Traveler podcast to get an overview of a potential destination. There aren’t that many places in the world that Chris hasn’t covered with a guest at some point, and the website is well-organized, making it easy to find a potential destination. Start off with the country first and then see if a guest has discussed a particular city of interest.

Thorn Tree/Lonely Planet forums

I like to use the Thorn Tree forums, which are owned by Lonely Planet, as a sanity check for my itinerary. Can I do a certain location in 3 days? Is the volcano worth seeing, or should I skip it? Are the buses comfortable enough for a 6 hour trip? Questions like that rarely receive attention in the other places I’ve mentioned above, but someone’s probably asked the question and received an answer from another person who’s already done it.


I like Nomadic Matt because he’s a traveler, not a tourist. He does focus on budget travel, so if you’re looking for more upscale recommendations, then this is not the place for you. However, if you’re counting costs on your trip, then this is a great site to check out, because he aims for travel on $50 a day or less.

Other useful tools

These are some tools that I have found to be useful along the way as we’ve traveled.



I remember the days when each airline and each hotel gave you a separate rewards card. Keeping them all together was a royal pain in the butt (literally, if that’s where you kept your wallet). Now, thanks to the miracles of modern technology, you don’t need to keep all of those cards. AwardWallet keeps them all together for you. Whenever I book a flight or check into a hotel, I simply pull up this website and find my rewards number to get the credit. They do have a paid version that keeps up with when your points will expire, but I’m not enough of a frequent flyer mile hound to find that worth the cost.

Note that some of the programs aren’t supported by AwardWallet. All this means is that you can’t use them to check your rewards balances. AwardWallet will still store your rewards numbers for you.


TripIt is an easy and convenient site for storing itineraries. It can either check your e-mail for you, or you can forward your confirmation e-mails from airlines, hotels, rental cars, trains, buses, etc. to their e-mail address, and they’ll add it automatically.

If you’re a frequent business traveler, then it’s worth it to try TripIt Pro. My business partner from my last company uses it because he travels frequently to speak at conferences or to see clients, and its lower fare and delayed/cancelled flight functionality has paid for itself a couple of times, making it a worthwhile economic investment.

We also use it to send itineraries to family members so that they know when we’re going to be away from home. I also use the iPhone app to pull up confirmation numbers when checking in at hotels or when picking up a rental car.


Before we complete a flight purchase, I’ll look up the actual seats on SeatGuru. I’m not that picky about my seats, but if I can find a slightly better seat without paying for the upgrade, then I’ll take it. I just don’t like getting the seats in the rear of the plane where you can’t recline and you’re next to the lavatory. I don’t recline often, but I don’t like not having the option, particularly if the person in front of me decides to get up close and personal by leaning all the way back.


When I’m going on a road trip, I like to take a look at the RoadNinja mobile application to see if there’s anything interesting along the way. It’s also good for finding places to stop along the way for a rest and food break.


I also like to use the GasBuddy mobile app when I’m on the road. When the car starts to get low on fuel, I pull up GasBuddy to see what the cheapest nearby station is. I’m not going to drive 20 miles out of my way to save a penny per gallon on gas, but if there are 6 stations right off of an exit on the Interstate, I certainly want to use the cheapest one.

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John Davis
John Davis is a nationally recognized expert on credit reporting, credit scoring, and identity theft. He has written four books about his expertise in the field and has been featured extensively in numerous media outlets such as The Wall Street Journal, The Washington Post, CNN, CBS News, CNBC, Fox Business, and many more. With over 20 years of experience helping consumers understand their credit and identity protection rights, John is passionate about empowering people to take control of their finances. He works with financial institutions to develop consumer-friendly policies that promote financial literacy and responsible borrowing habits.

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