A Completely Free Trip to Iceland With Points & Cash Back Cards, Including Spending Money!

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Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money!

Antonio is our newest reader success story to show folks it’s possible to travel without spending a lot of money.

A big thank you to Antonio for sharing his story!

Please introduce yourself to everyone and tell us how long you’ve been involved in the miles & points hobby.

Hello, my name is Antonio Riello and I have been traveling with points and miles for about 3 years. 

My first foray was an unconventional cross-country motorcycle trip.  I had a friend’s wedding to attend in Las Vegas in the fall of 2014.  I saw an opportunity to make the trip an “experience of a lifetime.”

Not only was it that, but it set me on a path for many “experiences of a lifetime.”  In short, my trip was sponsored by Vulkan, who make Brazilian jiu-jitsu gear, and North American Grappler’s Association who run tournaments for the sport.  The catch was I had to wear my Kimono coast to coast on my motorcycle.

As soon as those two lead sponsors were established, people started making PayPal donations to the Facebook event page.  I was able to offer advertising and some publicity for the two companies in return.  The individuals who donated were just generous folks who loved the idea of my trip.  And perhaps a few just wanted to see me make a fool of myself. 😉

I also used a few rewards cards to cover some of the rooms and fuel expenses.  This trip opened my eyes to unconventional thinking, which brought me to award travel.

After studying how award cards work, I jumped in head first and did an app-o-rama.  At the time it was easy because Target’s Redbird was alive and well.  Covering minimum spends took very little work for the several months Redbird was working with credit cards.

At first I tried to build a portfolio of points and miles.  Now I recommend focusing on a particular goal.  And then figuring out how to make it happen for cheap or free to newbies.

What was the goal of your trip?

To see Iceland without spending a penny of my own money.  It turns out Iceland isn’t easy with points and miles compared to most other places.  Hotel properties are very expensive and there was only one Hilton, and one Radisson hotel.

To my knowledge, the rest of the hotels are privately owned or owned by Icelandic chains.  And the car rentals were not cheap!

How long did you collect miles and points for your trip? 

I gave myself about 6 months to plan.

Which points did you save to take your trip?

I used AMEX Membership Rewards, Chase Ultimate Rewards,  and cash back rewards for most of the trip.  But I also used a Hotels.com free night.

What cards would you recommend to someone starting out with miles & points?

For a trip like this, I recommend getting cards that have flexible rewards points such as Chase Ultimate Rewards earning cards, or AMEX Membership Rewards points.  They can definitely be used to find beds in Iceland.

But the best value seems to be through Airbnb.  So if you can get their gift cards when eBay (or anyone else) is running a sale, jump on it.  Also, cash back cards were very helpful on this trip.  And if your rewards card gives you more value towards gift cards than cash, look at those options.

How did you search for and find the award flights?

I used Chase Ultimate Rewards to pay cash for my flights back and forth.

This isn’t really the best value for Chase Ultimate Reward points.  But I was a rookie and my goal was a free vacation.  I was happy with the value I got from the points.

At the time, Icelandair was not affiliated with any other airline award programs.  Today, you can book Icelandair flights with Alaska Airlines miles.

I still have Alaska Airlines miles from my first app-o-rama.  They have helped cover my flights for more recent trips to Iceland.  Your airport may have other options getting to Iceland on miles or points, but Boston is limited.  If you’re not concerned as much about dates, Wow Air offers very low rates a few times per year.

How did you find your hotel accommodations?

I spent 10 nights total in Iceland on this trip.

The first 3 nights I spent camping at a festival in the Westman Islands off the Southern coast.  The 5th night I went back to the mainland.  I used a free night I earned through Hotels.com.  I don’t normally book through Hotels.com, but it was the best option I had when booking co-workers for trainings at my full-time job.  It worked out in the end.

Before my trip, AMEX was offering a 20% bonus on Airbnb gift cards.  I used my points from the AMEX Premier Rewards Gold card bonus on those gift cards.

Night 6 I spent using one of those gift cards at a quiet cabin deep into the countryside.   My 7th night was at the Hilton back in Reykjavik using points from my Citi Hilton Honors Reserve card.

The final 3 nights, I stayed in a downtown apartment using the rest of my Airbnb gift cards.

What was the most challenging part about planning your trip? How did you solve it?

The fact that traditional points and miles didn’t go quite as far as they do in most places.

Hotels are expensive, there were no mileage awards to or from Boston, and rental cars were for the most part pricey.  I signed up for a few Capital One cash back cards because I knew there were limited rewards points opportunities.  I ended up with a Capital One VentureOne Rewards Credit Card and the Capital One® Spark® Miles for Business and Capital One® Spark® Cash for Business cards.  After minimum spends were met, I had $1,200 cash and used the Venture points to purchase gift cards that had a high rate on the resale market.

Ultimately, I ended up with about $1,700 cash from these 2 cards.  I used about $500 for my rental car.  And the rest was spending money.

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

Iceland is no longer a secret.  There are beautiful people; they are incredibly friendly and welcoming.

The landscape is beautifully unique and there is a lovable quirkiness to the culture.  If you like music and don’t mind late nights with friendly partiers playing guitars, check out the festival in the Westman Islands.  Really, any music festival in Iceland will be a good time.

And make friends with some locals, they are happy to talk to strangers.  I made friends that I go back to see yearly.

What did you learn about yourself on the trip?

I tend to travel alone.  In some ways, it has forced me to be outgoing and friendly to people.  I now have friends in other countries that I wouldn’t have made traveling in a pack.

On this trip I learned that almost anything is possible.  Through credit card cash back bonuses and some gift card reselling, I was able to not only pay for flights, car rental, and lodging, but also had more than enough spending money.

The only thing I actually ended up paying for was airport parking.  Everything else was covered with credit card rewards.

What would you say to folks looking to plan a similar trip?  Or to those who haven’t taken a miles & points trip yet!

Start planning, today.  You won’t regret free or cheap travel. 

This has become more than a hobby and I would say to some extent a lifestyle.  You’ll learn tricks to get all kinds of other products for a fraction of retail as well.  I’ve filled up my gas tank at 9 cents a gallon, just from buying Visa gift cards at the supermarket with a 5% back credit card.  When you play the game consistently, things fall into your lap every once in a while.

For example, I spend several hundred dollars per year on sporting goods.  But because I understand the miles & points game, I know I can purchase gift cards to make those purchases at 20% off, and get 5% back in Chase Ultimate Rewards.  Start playing the game, stop carrying cash, and subscribe to blogs.

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send me a note!  Emily and I would love to hear about how you travel with miles and points!