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Italy and Spain - Flights For Freeish've got that AwardWallet membership all fired up and you're ready to start accumulating miles, right?


For those of you still with me, I'll summarize how David and I accumulated enough airline miles to enjoy comfortable seats to and from Europe this June while spending very little cash. For a full trip summary, see my previous post About That OCD.

If you click on the picture, it will take you to the sign-up page. Thanks for using my referral link.

You're here reading our blog because you want to plan your own trip. Hurray! Obviously, your first decision is WHERE. Please do not randomly sign up for rewards credit cards with no firm destination in mind! I never recommend speculatively collecting mile/points "just in case". Airline and hotel loyalty programs can and do devalue their currencies without notice, and you could be stuck with a horde of points for which you have no use. And a bunch of hard pulls on your credit report which you most definitely do not want without a purpose.

Once you know where, figure out when. The more flexible you can be, the better. While hotel award space is usually plentiful (with the exception of certain tropical resorts and Hawaii), finding an airline award ticket is sometimes an exercise in patience and flexibility. And if you have 3 or more people traveling together, be prepared to split up. It's usually easy to snag 2 award seats on the same flight, but 3 or more is rare.

Still want to go? Then start planning about a year out. Airlines open up award space at varying times. Check out AwardGrabber to see when your desired flights will be open for award reservations.

Where, when, now WHAT DO I DO? Research which airlines fly to your destination. Google Flights is your friend. Think out of the box - if you're headed to Paris, you may be able to book a great seat from New York or Chicago and take a positioning flight from your home base. Always start with the longest flight first and work from there. I don't recommend booking round-trip tickets because one-ways offer much more flexibility. Here's what we did for our Italy/Spain trip coming up in 2 weeks:

I booked the BOS - FLR flight first using Air Canada Aeroplan miles for David, and United Mileage Plus miles for me. David had a small stash of Air Canada miles due to a previous trip, so I supplemented those with American Express Membership Rewards points I earned from a bonus on the Premier Rewards Gold Card. The United miles I earned from a bonus on the Chase Mileage Plus Explorer Card, supplemented with a transfer from Chase Ultimate Rewards.

What I wrote above is just a tiny example of the time and research that went into the flights for this trip. I spend hours every week researching, reading blogs, trying out new tools, asking questions in private forums, and running dummy bookings just so I know EXACTLY how to make all the puzzle pieces work. It's become my second job and my creative outlet. I also spend time maintaining our financial records.

(Shameless self-promotion: If you would like professional help booking your award seats, I am available for hire at very reasonable rates. Shoot me an email for more information:

Which brings up a VERY important point: if you are unorganized, in debt, or unwilling to strategically apply for and manage awards-earning credit cards, this hobby is not for you. If you are planning a major purchase like a house or car within the next several months, you should wait until that purchase is complete to plan your trip. David and I keep meticulous records and pay off our credit card balances in full every month. Lots of folks are concerned about their credit scores when applying for multiple cards. If you do the research, you'll find out that number of credit inquiries has only a small effect on your overall score. Only YOU can decide if that small hit is worth it. My go-to credit monitoring sites are Credit Karma for Transunion and Equifax and for Experian. They are free services and will alert you when something changes on your credit report. Also, almost all banks now offer free FICO scores with their credit card products.

Once you know where you're going, when you're going, and how you'd like to fly, it's time to research the award currencies that could possibly be used to pay for your flights. Most of the time, I use one airline's currency to pay for another airline's flights. The major airlines belong to one of three alliances, which allows the consumer to strategically choose among all the airlines in a given alliance. That's how I was able to use Air Canada and United miles to purchase a Swiss Air flight.

You may be confused by all this information. I understand! When I started in 2014 I was confused a lot of the time, but learned a lot by reading blogs and asking questions. For a list of blogs I love and read every day, check out my

Award Booking Service page. Also, I am happy to answer questions by email or in the comments.

Thanks for reading and supporting the blog!

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