8 Ways to Plan Amazing Travel Experiences in 2014


Greetings from the road! I’m in Johannesburg and preparing to board a Qatar Airways flight to Doha.

From there it’s Paris, Doha (again), London, New York, Los Angeles, and Dallas … in just over a week. What can I say—2014 is going to be a kick-ass year.

Once the calendar rolled over to January 1, I got straight to work on planning my travel for the first half of the year. The first big trip is a OneWorld Explorer Round-the-World ticket. I purchased the ticket last month from South Africa by calling the local American Airlines office.

To get to Johannesburg, I then booked a one-way award ticket on United, connecting in Washington, D.C. and then continuing on via South African Airways.

The award ticket doesn’t earn miles, but the Round-the-World ticket does—and now that we’ve hit 2014, I’ve got to get back to work on elite status qualification for the year.

This post contains my checklist for new mileage-earning opportunities, as well as a few things you can do to make sure you also get the year off to a good start. Enjoy!


1. Make sure you’re signed up for dining miles

If you haven’t done so before, register for the dining program of your choice, and connect your credit or debit cards to ensure you receive points whenever you eat at participating restaurants:

Once you sign up, these are free miles that you’ll receive automatically without doing anything special. You can register from anywhere in the world and receive miles from thousands of restaurants. Make sure you’ve got it set up!

The dining mile bonus is fun because it operates on a tiered structure. The more “dines” you have, the more points you’ll earn—although the count resets every January 1, so you’ll want to get a few dines completed now that it’s a new year.

Bonus: use your Chase Sapphire on the first Friday of each month for triple points. I always make sure to dine out when that day rolls around!

2. Put the American + U.S. Air Merger to Good Use

Even if you don’t follow travel news, you’re probably aware that American Airlines and U.S. Airways are in the process of merging. Overall, I’m not a fan of airline mergers. Despite all the fanfare (“We can serve you better… by reducing route options and raising fares!”) they usually end up lowering consumer choices over time.

Nevertheless, there’s often a silver lining. In this case, the positive aspects of the merger are:

1. The opportunity to earn more miles

2. The opportunity to combine miles between accounts (eventually)

If you fly on either airline over the next few months, you can now register to receive a 50% bonus on the other airline for a limited time:

At some point in 2014, we expect U.S. Airways miles to be converted to American miles. Over the past few years, U.S. Airways has periodically offered a number of chances to buy or “share” miles at a highly discounted rate. I’ve taken advantage of these promotions many times, and plenty of our readers have as well.

It’s hardly ever possible to acquire AA miles at the same discounted rate, so when the accounts are eventually merged, the value of those U.S. Airways miles will effectively increase. AA also allows one-way redemptions, something that U.S. Airways doesn’t.

3. Get a few credit cards and carefully manage them

Credit card signup bonuses and ongoing points from spending have allowed me to go all over the world. I’ve documented the process many times on the blog, especially through the Frequent Flyer Challenge and other travel hacking posts.

I know some people find the process of deciphering which cards to get (and how to best use them) somewhat overwhelming. If you can only get three, start here:

If you’re eligible for this card, there’s no reason why you shouldn’t have it. I use it every day and it takes up the most-used space in my wallet.

Along with its cousin, the Chase Ink Bold provides an even bigger bonus than the Sapphire (50,000 points) and also earns 5x points on certain spending categories. More on this in a moment!

The personal version of this card was my very first travel hacking companion. I’ve had it for more than a decade now (yeah, I’m old). I added the business version a while back for an additional signup bonus, and ended up keeping it because it helps me get closer to Starwood Platinum status each year.

4. Join the hunt for Vanilla Reloads or other “manufactured spend”

Last year our readers earned millions of miles (yes, millions!) by taking advantage of a time-limited opportunity to purchase “Vanilla Reload” prepaid gift cards at office supply stores. They received 5x the points by using the Chase Ink Bold or Ink Plus cards, before depositing the funds back into their accounts.

In other words, you could effectively “buy money” for a nominal fee, and receive up to 25,000 Ultimate Rewards points every month for your efforts. Very nice! I earned about 70,000 points myself and went to Malaysia with them, all in exchange for a couple of hours work.

This was a huge deal while it lasted, and after experiencing a surge in volume all of a sudden, Office Depot and co. finally stopped letting customers use credit cards to purchase the cards—thus ending the major deal.

However, the deal lives on in lesser form! It’s still possible in many states to purchase up to $5,000 in Vanilla Reloads from CVS stores every month and earn 1x points.

Thanks to my travel hacker friend Wandering Zito, who occasionally wanders to Florida, I’ve been able to acquire about $15,000 in Vanilla Reloads in recent months. I may not earn the full 60,000 possible points from them this year, but I’ll take advantage of it whenever it’s possible.

Vanilla Reload Road Trip

Recent scouting has reported the following data on all-important VR availability:

Oregon: no CVS stores (womp-womp)
Nevada: CVS won’t sell them with a credit card (stick with blackjack)
Florida: Plenty of stock (cha-ching!)
Washington, DC: Plenty of stock… and you can buy up to $5,000 a day (whoa! It’s a reload gold mine over there)

Vanilla Reloads aren’t the only option for manufactured spend. Head over to this Flyertalk forum for info on other locations, as well as other prepaid cards.

Action: If you can’t get Vanilla Reloads in your area, don’t worry about it. But if you can, you might as well take the time to work on your 5,000 free miles per month.

5. Stock up on other gift cards

This one is easy. Even if you can’t get Vanilla Reloads in your area, there are other opportunities you can pursue. As mentioned, the Chase Ink Plus and Ink Bold cards provide 5x points on all spending at office supply stores.

Because all spending counts for the bonus points, I regularly visit Office Depot to pick up gift cards for some of my favorite vendors: Starbucks, iTunes, Amazon, and Barnes & Noble, among others. I then load the balances from these gift cards on my account—and earn 5x points from the purchases, instead of the 1x points I’d usually receive.

I’ll never purchase anything again from these merchants without earning 5x instead of 1x. If you have one of the Chase business cards, do the same!

6. Get your $200 credit from the American Express Platinum card

Every year, the American Express Platinum card offers a benefit where you can receive a $200 statement credit on the airline of your choice. Most people use the benefit to receive reimbursements for checked baggage fees or on-board purchases—but that’s not usually the most optimal use of the rebate.

I don’t have much need for baggage fees (I never check bags, and thanks to elite status they’d be free if I did), but I do purchase plenty of American Airlines flights. Once January 1 came around, I went to and purchased four $50 gift cards. Less than a week later, a $200 credit appeared on my statement. Boom!

It’s like an annual rebate of almost half the fee. You can also now get free Amazon Prime for the first year, as well as a rebate of your Global Entry fee. Even though this card carries a hefty annual fee, for me it’s worth it.

Disclaimer: I’ve received this benefit three years in a row with no problems, but be aware that your experience may vary when pursuing this strategy, since AmEx does not publicly list the purchase of gift cards as an option for receiving the credit.

AmEx is also opening a number of its own airline lounges around the Americas, starting in Las Vegas but now including Dallas and Sao Paulo. New York’s La Guardia is on the way, along with others.

Airline lounges are not created equal: in some you’ll be lucky to get a packet of stale cookies and a lukewarm cup of bad coffee. The new “Centurion” lounges, though, are the real deal. On a recent visit to Las Vegas I was amazed by the full meal and bar service. In Dallas, they even offer complimentary spa treatments. It’s as though Virgin Atlantic has moved to the U.S.!

7. Use Amazon payments to earn 1,000 free miles every month

You can earn 1,000 free points or miles every month by using Amazon payments, and it takes about one minute each time you do it.

The process is pretty simple:

1. Go to and set up a bank account (it uses your regular Amazon account… you do have one, right?)

2. Select “Send Payment”

3. On the confirmation screen, make sure you don’t choose “Cash Advance” – this can generate interest charges on your card

4. Send the money to a trusted friend, who can then claim the funds and send another $1,000 back to you after a couple of days

5. Do this every month and you’ll each earn 12,000 points or miles a year. This can also help with meeting minimum spend for a new credit card.

Note: don’t go crazy with this strategy. Amazon seems to have no problem with people sending $1k back and forth each month, but if a bunch of people start creating multiple accounts in an attempt to game the system, it could become difficult for everyone. As always, focus on the long-term!

8. Manage all travel hacking for the long-term

Every day I hear stories of new travel hackers who are earning points and miles, then putting them to use for worldwide travel. You can do this too!

Last year I earned more than 1,000,000 miles, sometimes by doing crazy things like buying a bunch of gift cards, but more often just through normal activities. If you manage your accounts well, learning new strategies over time, you can earn miles and points for years and years.

Opportunities for non-U.S. residents continue to increase as well. There are now some decent cards available for Canadians and Australians, among others. The U.S. Airways purchase miles option is always available worldwide, and many of our international readers have used it to travel on great Star Alliance carriers including Singapore Airlines, Lufthansa, Turkish Airways, and Air New Zealand. Amazon payments has promised to expand to more countries soon.

In short, instead of tightening up, it’s actually become easier to earn large amounts of points and miles on a regular basis. Even though I’m no longer visiting every country in the world, I still plan to do enough travel hacking to go anywhere I want, anytime.

Speaking of, I’m now underway on my first Round-the-World trip of the year… and it’s time to head to the airport yet again. Next stop, Doha!

Happy travel planning, and happy January to each of you.

– Chris


Image: JaCash

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