A while back, I received a postcard informing me that I had won a free 7-day cruise for two. The available cruises were to the Mexican Riviera or to the Caribbean. I love the Caribbean. (México, too!) All that was required to get the free cruise was to attend a timeshare presentation. (You probably saw that coming.) I kind of expected that. So my wife and I went ahead and attended the presentation. And, as promised, I received my free cruise certificate. So far, so good. But it soon became evident that that “free” cruise wasn’t free.
The company offering the free cruise requires you to pay around $300 for various fees, taxes, “paperwork processing”, and whatever else it costs $300 to do. I hadn’t expected to pay anything up front, but $300 for a 7-day Caribbean cruise is still a great deal. So I sent in the money.
Then I read the fine print. (You’re right, I should have done that first.) The fine print says the “free” cruise was only available during the last three months of the year, which they consider low season — and which the National Weather Service considers the last part of high hurricane season. Out of those three months, three weeks were considered high season. That leaves only 10 weeks’ worth of low season out of 52 weeks in the year. I was not able to take a cruise during those 10 weeks.
Conversely, should you choose to cruise during high season, the company will happily book the cruise for you…at the same rate you’d pay if you booked it yourself through the cruise line… plus the $300 you’ve already paid for the “free” cruise.
Let’s look at this for a moment: I found a cruise that I am interested in taking. On the cruise line’s website, the sailing is advertised for $649. But if I booked with the company that awarded me the “free” cruise, it would cost $649, plus the $300 in fees, etc. I’ve already given them, plus any additional taxes and gratuities levied by the cruise line. That means the $649 cruise that was ostensibly free would end up costing me approximately $1,000 or more.
Several times I called the company providing the cruise to confirm what I had read. I called them several times to confirm what exactly constituted “high season” and what constituted “low season”. I called them a couple of times to postpone the cruise date just so I could keep my reservation. It was becoming clear there was no way I’d be able to cruise during low season. And there was no way I was going to pay full fare during high season, plus $300, for a cruise that was supposed to be free.
Should I Walk Away?
Seeking advice, I put the question out to my Facebook friends and family: Should I leave $300 on the table and walk away from the deal? The answer was an overwhelming “Yes”. After agonizing over not wanting to lose a “free” cruise that I had already committed $300 to, I decided to leave it on the table and grudgingly walk away. I really hated to waste good money like that. One person offered some sage advice: You may lose this battle, but don’t lose the lesson. Or, looking at it another way, I had just paid $300 for a class in Life 101.
It was then that I made a vow; a self-directed, post-course homework assignment, if you will: By the time the next opportunity to take a cruise comes up, I will find a way save at least $300 between airfare and the cost of the cruise itself. To accomplish that goal, I decided to become a savvier traveler. I may have lost $300, but I was determined not to lose the lesson.
Using the internet as the world’s largest library, I checked out several travel websites. Using these sites as textbooks, I gleaned as much information as I could. What I found out was eye opening. Like anything worth doing, it took a bit of effort, dedication, and determination, but I believe I got high marks in this class. And yes, you can do this, too.
Lesson 1: Airfare
Two Websites That Made All the Difference
To start with, go to Nomadic Matt’s website and browse the wealth of information he has made available to you. Pay particular attention to the Travel Tips page, and the How to Find a Cheap Flight page. Then sign up for Matt’s newsletter. Each edition he sends out has good information about traveling, secret sales, airline mileage tips, etc., plus news on what he’s been up to lately. Matt is a world traveler and knows what he’s talking about. So it is worth your time to become a student of his.
Another excellent resource is Brian Kelly, better known as The Points Guy. His site is full of tips on how to maximize miles and travel points. Though his advice tends to lean toward using and signing up for rewards credit cards, The Points Guy includes plenty of other tips, perks, and airline news that most of us would otherwise not know about. Signing up for his newsletter is highly recommended.
Flight Search Engines
I recently purchased a cross-country airline ticket after checking a couple of flight search engines. Fares doubled the day after I bought the ticket. The day after that, Travelocity showed fares back down to nearly the range I paid while Skyscanner still showed the much higher fares. Ironically, for the European trip I’ll mention later on, the situation was the exact opposite with Skyscanner saving me almost half over fares Travelocity and other sites listed.
Experienced travelers will tell you to check many different travel search engines and check them often. Do not become obsessed, but do check them once or twice a week. Or, better yet, sign up for their fare alerts and let them do the work for you.
The more I learned, the clearer my strategy for using flight search engines became. I always start with Skyscanner. They usually have more flight options available than the other guys. My search ends there and I’ll book right then if I find a price I cannot pass up. If Skyscanner’s results haven’t displayed anything I like, I’ll set up a fare alert with them. They will automatically notify me by email if prices change, up or down.
Next, I’ll search Momondo. From there, I’ll check Kayak. If I still don’t find any fares I like, I’ll start my search again using different travel dates and, if possible, alternate airports. On very rare occasions I will search some of the cheap airfare sites to see what they have. I’ll use those results to modify my search criteria.
If I have a destination in mind but no firm travel dates, I’ll look at Google Flights. I enter my departure airport and my destination. Then, I click the Departure date box (the one with the calendar icon). A calendar will pop up with fares listed below each date. The calendar will allow you to see typical airfares for up to 11 months in advance of today’s date. Using the results, I can choose the best airfare at a time of year that best fits my schedule. I will use that information and go back to Skyscanner, or book through Google Flights. (Google Flights will take you directly to the airline’s website to book your ticket(s).)
Have some fun with Google Flights; click the Explore button on the left menu to see flight info for other destinations you can fly to from your selected departure airport.
Lately I’ve become a fan of Going, formerly Scott’s Cheap Flights. They send out flight alert emails with fare deals ranging from 40% to 90% off regular fares. When you sign up, you add in a couple of your favorite airports. Any airfare price drops that Going finds on flights departing from those airports will come straight to your inbox. The emails contain the details, links, just about everything you need to know to book the flight. And it’s free! The premium versions get you more deals sooner, plus some of those mysterious mistake fares you hear about.
Sometimes, just for fun, I’ll look up fares directly on an airline’s website. On occasion I have found either a better itinerary or lower fares this way. It doesn’t happen often, but it works often enough that it remains part of my strategy.
One thing I disagree with is the use of the fare predictors. Kayak has one. You enter your flight parameters and it predicts whether you should buy now because fares may go up soon, or wait because fares may drop. For a domestic trip, I tried a couple of these price prognosticators and got conflicting information: one said fares were going to rise, the other said they would fall. Putting more confidence in the “80% certainty” of the fare drop prophesied by the more well-known site, I waited. What they don’t tell you is that “80% certainty” prices will fall means there’s a 20% chance prices will rise…which they did…by over $50. That was enough to dissuade me from using them in the future.
Things to Keep in Mind When Searching for Airfare
Something else to think about: how valuable is your time? Yes, you can (or you should be able to) easily shop around and save $7 or $10 or even $25 on a particular airfare. But is it worth it if you spent two hours comparing different sites to save that $7? You might have saved $50 by flying into and/or out of an alternate airport. But if you spend $30 in gas to get to and from that airport, plus 3 hours on the road in traffic, plus an additional $25 in parking fees versus parking at the primary airport, is it worth the $50 you saved on the airline ticket?
How soon should you start looking for airfares? As soon as you know when you are going. There’s no real magic timeframe for getting the best deals. You’ll see many sites that recommend a four-to-six-week window for domestic US flights, while endorsing an 89-day lead-time for international flights. Most of the time this advice is solid, though not infallible; at times the best fares can be found outside these timeframes.
Before you aim for that 89-day international window, keep in mind the popularity of your destination and season during which you’ll be traveling. As an example, Cancún, México, is a hugely popular travel destination, especially during Spring Break in the US. Many resorts there are booked months in advance. Finding a 60% off one-day sale on airfare to Cancún 89 days before you travel does you absolutely no good if your hotel was sold out four months ago.
August is a popular time to travel in Europe. As with Cancún, hotels tend fill up early. Here again, that 89-day window may not help if your hotel is already sold out. Of course, this also applies to the four-to-six-week window for US flights. It is doubtful you’ll have much luck getting a hotel in Vail, Colorado, during ski season one month before you plan to travel there. If you want to try out that 89-day theory, secure your hotel first, then look for airfare. It’s easier and cheaper to get a refund if you need to cancel or change your hotel reservation than it is if you need to cancel or change an airline reservation.
On the other hand, waiting until a week before your departure date to book your flight is a huge gamble that can potentially pay big rewards for your patience. Last-minute deals on flights, cruises, hotels, etc., abound all over the internet. But the key word here is gamble. That’s all I will say about it.
To use a baseball analogy, don’t expect to hit a home run with deals on airfares every time. Sometimes a single or double will do just fine. That cross-country airline ticket I purchased is a good example. I saved around $50 over fares that were advertised on the popular travel search engines and purchased the ticket within the four-to-six-week window before my travel date. Unfortunately, a fare alert informed me two weeks after I bought the ticket that there was a one-day sale that listed fares $70 lower than what I paid. Of course, I would be happier had I saved the entire $120, but I’ll take a $50 savings any day.
Lesson 2: Airline Miles and Rewards Points
Earning Miles and Rewards Points
Want to save more money on airfare? Consider joining the major airlines’ frequent flyer programs like Delta’s SkyMiles, United’s MileagePlus, and American’s AAdvantage. It’s free to sign up. The trio have partnerships with other airlines around the world: Delta is a member of SkyTeam, which has nearly 20 international partners; United belongs to Star Alliance, which currently has 26 international partners; American is a member of OneWorld, which currently has 14 international partners. Between the three majors’ mileage programs, you should be covered for the vast majority of your flights, especially if you are flying overseas. Personally, I belong to all three programs. If you fly Southwest or JetBlue often, consider joining their programs, too.
So far, I’ve taken two free round trips with Delta Air Lines, one free round trip with United Airlines plus two more in the planning stages with the miles already in my account, and my last trip earned me enough miles for a free flight with American Airlines. By the way, the shortest of these free trips was a coast-to-coast, round-trip flight. And this was before I became a savvy traveler. Imagine what could have been possible had I been more diligent about accruing miles when I first joined these programs.
For those of you in my position — meaning those who fly once or twice or so a year, if that — it still makes sense to join the majors’ loyalty programs. Why? Because you want to make every trip count. You’re probably not concerned with trying to reach elite status with a particular airline since you don’t fly that often, and it will take a considerable amount of time to reach that level. So you search for the cheapest fare on whichever airline offers that cheap fare.
But if you belong to more than one loyalty program, chances are you are at least accumulating miles on someone’s program on just about every flight you take. And those miles do add up. Even if you don’t build up enough miles for a free trip, an upgrade to first class is a nice reward for your patience and persistence. Just remember to have some sort of activity in your mileage accounts periodically so your hard-earned miles do not expire before you’ve had the opportunity to reap the fruits of your mileage-earning labor. There are numerous ways to do this without ever leaving the ground. Refer to the airline’s mileage program for details.
We haven’t even discussed rewards points yet. Try this: if you have a credit card that has a rewards program where the points are redeemable for travel, use the card for items you were planning to purchase anyway. Keep that free upgrade or trip in mind and adjust your buying habits accordingly. For example, if you are in the market for a GoPro, use your rewards card to pay for it. Now, not only do you have a new camera to capture memories of your upcoming trip, you are a few hundred points closer to actually taking that trip for free. Do not go into credit card debt trying to earn free miles. Again, the trick here is to use the rewards card for items you were going to buy anyway.
Level Up Your Miles
Level up this strategy by shopping through the airline’s shopping portal. They will have a large selection of stores they partner with from apparel to electronics to sporting goods to restaurants to home improvement and more. Make sure you log in to your airline’s rewards program first. From there, choose the store you want to visit and shop as you normally would. You might even find that GoPro. Sometimes the shopping portal will have a special offer where your purchase will earn double, triple, or more miles for every dollar you spend.
Want another example? Chinese billionaire (yep, that’s billionaire with a “B”) Liu Yiqian had the winning bid at a Christie’s auction in 2015 for a painting by Amadeo Modigliani called “Reclining Nude”. The winning bid was US$170.4 million. Yiqian put the purchase on his American Express Centurion card. And he earned rewards points for that purchase.
With just that one purchase, Yiqian and his family can use those points to fly anywhere in the world for free — probably first class — for many years to come. (In case you’re wondering, that card, also referred to as “the Black card”, has an initiation fee of $7,500, an annual fee of $2,500, an annual spending requirement of at least $250,000 or more per year, and is available by invitation only. No, I don’t have one.) Even the ultra-rich who can afford to do everything first-class pay attention to rewards points. There’s no reason why we can’t do it, too.
One nice thing I learned on a recent trip to Jamaica: You can use rewards points from a credit card to pay for an airline ticket and still earn mileage for the flight with the airline. Imagine my surprise when I saw my next mileage statement and realized the free trip I just took to Jamaica put me one step closer to yet another free trip! Yes, there is a caveat: it works only when you use points accumulated on the card to pay the airfare. It does not work if you transfer points into an airline’s mileage program and then buy the ticket with miles. Refer to the airline’s mileage program for details.
Lesson 3: Accommodations
My strategy for accommodations is pretty basic. I always start out by searching Hotels.com. I am a member of their Hotels.com Rewards program, which entitles members to one free reward night for every 10 nights booked with them. Their listings include hostels, vacation rentals, motels, and everything from budget to luxury hotels. Through their rewards program, I’ve stayed in places across the US and abroad for free.
In the very rare instance where I can’t find a hotel through Hotels.com that suits my needs, I’ll look at Best Western. I’m also a member of Best Western’s rewards program and earn points towards free hotels stays with them, too. I mention Best Western here because I noticed I had been staying with them more than with any other hotel chain. So it made sense to join their program. Travelocity has come in handy in a few instances. Between the three, I should be able to find something that works for my budget and itinerary. Skyscanner integrated hotels into their site since I began my journey to savvier travel so I will incorporate Skyscanner Hotels into my strategy.
If you’re not already a member of any chain’s rewards program, look back on your past trips. Are there one or two hotels you tend to frequent more than others? If so, join their programs.
(Yes, there are many more options for accommodations such as Airbnb, Booking.com, Couchsurfing, Hostelworld, Vrbo, and others. I cannot comment on them because I have not used them.)
Lesson 4: Cruises
If cruising floats your boat, a visit to Vacations to Go is a must. They list fares, last-minute and no-so-last-minute, which are up to 80% or more off advertised rates. You can find these deals just by visiting their site. I recommend signing up for their newsletter. Some of the cruise deals they have include credit you can use while on board the ship.
Once you find and take that cruise, sign up for the cruise line’s loyalty program. You’ll get some nice perks the next time you sail with them. Sail with them enough and you can enjoy benefits like offers and discounts available only to members, free drinks, priority spa and dining reservations, complimentary laundry service, and priority embarkation/debarkation. Die-hard veteran cruisers can earn free cabin upgrades or even a free cruise. I belong to Carnival’s VIFP Club and to Norwegian Cruise Line’s (NCL) Latitude Rewards Program.
Final Exam
With all this information, there should be no reason for you not to pick up air miles and/or rewards points on any purchase you make, or any flight or cruise you take. And there is no reason for you to go to sleep at a hotel and not wake up with a bigger rewards points balance.
How I Put These Lessons to Use
Now that I’ve become a savvy traveler (and shown you how to become one, too), how did I do on my first assignment?
By taking advantage of fare sales on a European trip, I saved enough between airfare and the original cost of the Baltic cruise we took there to pay for round-trip airfare to the departure port AND the cruise fare for that “free” Caribbean cruise for both my wife and I, less about $100. That was from just one trip.
How did I save that remaining $100? My wife and I decided to change that “free” Caribbean cruise to a shorter 5-day getaway cruise from a local port. The price was still the same $649. Vacations to Go sent out a newsletter informing their subscribers of a huge cruise sale. I quickly took advantage of it. The cost of the cruise was half of the regular rate, plus we got $70 to spend on board the ship. Later, after the sale, I checked again. Indeed, close to the sail date, rates crept back up to regular price. The cruise eventually sold out.
In a way, becoming a savvy traveler provided the chance for my wife and I to take that cruise for free after all. Plus, with the savings from that getaway cruise, we are about $400 away from paying for airfare and hotel on our next Caribbean trip. Well worth the $300 lesson, wouldn’t you agree?
Originally posted in May 2019 as a four-part series. Updated 9 May 2022 to update links and consolidate into a single post. Updated 24 January 2023 to include Going as part of my airfare search strategy.
Photo credits:
Cruise ship in featured image – Pixabay; Airport departure board – Gerald Friedrich from Pixabay; Credit cards – Republica from Pixabay; “Hotel” – StockSnap from Pixabay; 2nd cruise ship – Eddie Hernandez from Pixabay; Passport and carry-on – cytis from Pixabay.
Disclosure: Please note that this post may contain affiliate links. By clicking them, you get access to the same products and services I use. At no additional cost to you, I may earn a small commission if you make a purchase. The commission I earn goes to help keep this site running.
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