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“I Crossed All 7 Continents in 4 Months for $241 in Flight Costs”

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Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers. Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:  Wise Flys

David helps Wise Flys readers save up to 90% off flights and earn free hotel nights!  You can also follow him on Facebook.

Loving the Views at the Castelo de Sao Jorge, the Highest Point of Lisbon, Portugal

How and when did you start collecting miles and points?

I discovered this amazing hobby on a cold New York day in the fall of 2011.  Living at home after college with limited vacation funds, I was researching cheap travel techniques for my next trip to Ethiopia for some volunteer work.

The term “travel hacking” came up in searches and I was intrigued.  One website led to another until I eventually stumbled upon the Mecca, FlyerTalk.  I was immediately hooked, and spent the next 3 months glued to the computer screen (3 to 4 hours a day after work) learning as much as possible from the nooks and crannies of FlyerTalk threads.

Why did you start your blog?  What’s special about it?

The following spring I planned an epic trip that crossed all 7 continents in 4 months for $241 in flight costs.  After returning in 2013, word spread about my journey.  Friends and family became curious (because I am not independently wealthy to afford such an excursion) and wanted to learn more on how to travel internationally on the cheap.

Havana, Cuba, Was Such a Unique City. With All the Stone Streets and Antiquated Architecture, It Felt Like We Went Back to the 50’s

A local newspaper interviewed me, and I soon composed the Memoirs of Napoleon Streisand, a book about my trip.  At the time, I was using the pen name Napoleon Streisand.

Now, I was spending hours responding to emails helping readers with their trips as a labor of love.  It was fulfilling helping people bypass the difficulties of navigating FlyerTalk forums to plan their trips around the world.  Eventually, I found myself answering the same questions with the same answers.

Wise Flys grew out of this experience.  Creating a blog was a better way to serve people wanting to travel more and spend less.  Unlike many other blogs, we focus on helping beginners.

At Wise Flys, we like to emphasize simplicity.  We share basic formulas and strategies to get the most out of every hard-earned point.  Our interest is moving toward points for destinations.  For example, a post is under development on how one credit card sign-up bonus can yield 2 round-trips to Hawaii in coach.

Making the Most of Our 12 Hour Layover in Paris, We Checked Our Backpacks at the Airport and Explored the Beautiful City All Day. It Was Much Better Than Sitting in a Lounge All Day

What’s the one single thing people can do to get more miles?

I’m going to avoid the obvious and cliché answer of credit card sign up bonuses.  While highly valuable and a major step to achieving your travel goals, let’s highlight everyday spending as another avenue to increase the flow of points.

The best way to get more miles is through maximizing every dollar spent on the right credit card.  For example, let’s say you spend $5,000 a year in groceries (a little less than $100 per week).  Wise Flys recommends using a credit card that earns 3 points for every dollar spent at supermarkets.  The Blue Cash Everyday® Card from American Express is one example with this feature.  In this scenario, you would then earn an additional 10,000 AMEX Membership Rewards points.  This points accumulation strategy can put you over the edge for a trip.

In Plettenberg, South Africa, Jumping From the Highest Bungee Jump in the World. I Feel Crazy for Not Doing It Twice

What’s your most memorable travel experience?

As a solo traveler, my most memorable (and expensive) experience was in Antarctica.  I went swimming with the penguins and spent a night under the stars with no tent.  The entire experience was pretty cool.  (Sorry, I couldn’t resist the pun).

Now that I’m blessed with 2 lovely lady travel companions, I’ve become more focused and creative in designing our family travels as the points breadwinner.  Having a child hasn’t hindered international jetting.  We travel the world and make amazing family memories together.

Our most recent and memorable trip took us to Europe and Africa last month.  With my wife and daughter, we went to Portugal, Morocco, Tenerife (Spanish island off Africa), and London.  It was such a great buffet of cultures, languages, and currencies.

Surfing in Portugal, Morocco, and Tenerife was the highlight of the trip.  My wife and I love to surf together.  Our daughter Bella has also caught the ocean bug.  This trip she joined us in the water, wetsuits and all.

The Rough Waves Were Crashing Next to Us at the Natural Pool in Bajamar, Tenerife. Tenerife Is a Spanish Island Off the Coast of Northwest Africa

One benefit of travel is cultural intelligence and awareness.  As parents, we love watching Bella interact with kids from all over the world.  By the age of 4, our daughter has been to 12 countries on 5 continents.  We would have never been able to afford all this travel without using points.

What do your family and friends think of your miles & points hobby?

After 7 continents, 50+ countries, and dozens of free hotel nights, most have taken my advice and enjoyed amazing trips for a fraction of the cost.  It has been rewarding to see my friends and family take trips using miles and points.  Some friends and family, however, do not resonate with my hobby.  But I think they’ll eventually come around with enough family vacation photos displayed on Facebook.

Is there any tool or trick which you’ve found especially useful in this hobby?

A frugal mindset and willingness to travel light and in coach.  We aren’t rich and try to save any chance we get.  I don’t mind flying Spirit Airlines.  There, I said it!  Haters gonna hate.

Since I wear the points in the family, I’m always looking for the best value in every opportunity and stretch each point to the limit.  Think of your miles and points as dollars.  You would never throw away dollars or misuse them, right?  The same goes for points.  Make each redemption count.

Feeling Quite Small Next to the The Hassan II Mosque, the Biggest Mosque in Casablanca, Morocco
Timing is key.  We plan our big trips years in advance sometimes.  To get the best award rates and availability, it’s best to give yourself at least 6 to 12 months of planning.

Because we have been involved in this hobby for a few years, we have a good stash of points to take last minute trips or book hotels in a pinch.  If you are new to the game, be sure to give yourself enough time.  The last thing you want is to have finally earn the points but find no availability for the flight or dates you wanted.

Get organized.  I know a few people who missed out on their sign-up bonus because they didn’t keep track of their spending.  That’s like the equivalent of losing out on $500, or even $1,000!  Be diligent, and have a clear plan to never make that mistake.

The best tool is my handy dandy Google spreadsheet.  It organizes all of my credit card activity.  When to complete the minimum spending, when my annual fee is due, and plenty of other data points.  It is a foolproof system to stay on top of things.

I usually only share my special spreadsheet with clients, but I want to give back to Million Mile Secrets and its awesome readers.  Read to the bottom to see how you can get it too.

The Colors and Architecture of the Palace Were So Beautiful. Pena Palace Is Nestled in the Mountains of Sintra, Portugal, and Belongs in the Next Disney Movie…

What was the least expected way you’ve earned miles or points?

We stayed at the Marriott in Hilton Head, South Carolina, a few months ago for my wife’s work-related trip.  The hotel was covered by her job and we were happy with the free hotel nights.

Upon checking out, we gave the front desk her Marriott account number thinking it would score us a couple thousand points.  Nothing major, but better than nothing.  After checking her account, those nights yielded a little over 15,000 Marriott points.  I wasn’t expecting to get that much.  This score gave us a free night in Boston the following month.

What do you now know about collecting miles and points which you wish you knew when you started out?

Don’t squander your miles and points.  I wish I did more research or consulted with someone before taking action.  What pains me the most is thinking about all the wasted miles and points I spent on horrible redemptions.  Kind of like winning the lottery, points earned quickly and easily don’t have much value attached to them.

When I first started, my logic was “I have 50,000 American airlines miles.  Sweet!  I want to use them to go from New York to Miami.  Great, there is a round-trip for 45,000 and will have 5,000 points leftover.  That’s a win!”

Bella Is Getting Some Rest While Waiting for Our Flight to Tenerife From the Airport in Casablanca, Morocco. Our 2 Backpacks and a Rolly Bag Was All We Packed for Our 4-Country Trip. She Is Adjusting Well to Becoming a World Traveler

What’s wrong with that common rookie mistake is that I didn’t know there are ways to get that flight for fewer points.  If I had transferred my Chase Ultimate Rewards points to British Airways at a 1:1 ratio, I could have gotten the same exact American Airlines route and plane for 15,000 miles round-trip.  That 45,000 miles I spent could have been 3 round trips instead of one.  Knowing these tricks and redemption sweet spots is what makes your miles and points last for several trips.

Moral of the story, know what you are doing before you do it.  To know what you are doing, do the research or consult with someone who does.  Ask questions.  Ignore negative replies or terse responses from veterans.

If you are new to miles and points, don’t hesitate to reach out to someone who knows a little more.  😉

What would your readers be surprised to know about you?

I love organic gardening and growing my own food.  My garden is designed with a self-watering system.  When I would come back from weeks of travel, all the plants were thriving.  This season I grew some purple tomatillos, white eggplants, red okra, kiwano melons, and dozens of other edible plants.  The other day I harvested 17.6 pounds of purple sweet potatoes.

Wandering Through the Chilly Streets of London at Night During the Christmas Season

Any parting words?

Thanks so much for reading.  I am offering a free E-Book, a credit card spreadsheet, and a chance to win a $50 visa gift card.  Head over to wiseflys.com/MMS.  These goodies will only be available until 11:59 pm Eastern Time on Sunday, December 10, 2017.

I will leave you with my favorite travel quote.

The world is a book, and those who don’t travel only read one page.
Augustine of Hippo David – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)