“Instead, we chose to road trip the USA!”

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Welcome to the next interview in our interview series where travel bloggers share their insights on having Big Travel with Small Money!

Miles & Points Interview: Dovertime

Kyle runs dovertime to help ordinary people achieve their extraordinary travel goals.

Dovertime - Interview With Kyle

Wife and I at The Bean in Chicago

How and when did you start collecting miles and points?

My dad signed me up for a frequent flier account on our first trip to Hawaii.  When I turned 18 I got my Alaska Airlines Visa credit card and the rest was history!  I learned valuable lessons from my parents about paying the credit card balance in full each month.

I’ve treated my credit card like a bank account, closely monitoring my spending and never charging more than I could pay at the end of each month.  With that said, after I turned 18, EVERY purchase went on this credit card!

I chose to go to a school cross-country and traveling back and forth definitely helped.  I also held a position in college that required me to travel frequently.

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

I have been earning and burning miles for years and have helped numerous friends and family members sign up for credit cards to fund their epic travel adventures.  After much deliberation and many conversations with my wife, I launched Dovertime!

I would’ve started a blog long before but I couldn’t think of catchy name.  I was in my car en route to a client’s office when I read the license plate of the car in front of me; REXPRT.  I started thinking about names that work with Dover and Dovertime hit me like a freight train.  It was perfect!

Dovertime showcases great photography and lots of number crunching!  I like big, bright, in your face photos!  Photography is an important part of my life and I believe that powerful photos stir up excitement about destinations.

I’m a numbers guy at heart and am always trying to provide tips to get the most value out of your points and miles!

Dovertime - Interview With Kyle

Surfers at Bondi Beach in Australia

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

Seeing people use cash leaves me #SMH (shaking my head)….  Start thinking outside the box!  People need to get in the mindset that every single purchase needs to be made on a credit card!

Once you realize that every purchase can be made with a credit card, then figure out how to maximize your rate of return.  For instance, some points earning credit cards may earn 2x points on gas purchases.  But you may have another credit card that earns 5x points at a place where you can purchase gas gift cards.

One credit card may earn 3x points for booking flights, but another one might give you 2x points for travel plus 2x points through a shopping portal.  Give up the greenbacks and embrace the plastic for everyday spending.

What’s your most memorable travel experience?

My honeymoon in the fall of 2012 was insanely cool.  I thought that my points and miles would take my wife and I to Tahiti or The Maldives for a week.  I was flat out wrong!  Instead, we chose to road trip the USA!

I completed a major app-o-rama to earn serious hotel points.  I then landed 15,000 Hertz points at a fraction of the cost during the Daily Getaways promotion by American Express.

With all of the points and miles we flew from Oregon to Connecticut, rented four different cars over three and a half weeks and flew back from Florida.  We stayed in amazing hotels every night for free.  We visited fifteen States along the East Coast.  And we drove Mercedes SUV’s and Chevrolet Corvette Convertibles!

Could we have done this without points and miles?  Absolutely!  But it would’ve put an extreme dent in our savings account or we might not have been able to stay in Park Hyatts!  Air miles and hotel points allowed us to complete an amazing honeymoon without having to sacrifice anything.

Dovertime - Interview With Kyle

My wife and I in Clearwater, Florida

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

It took me awhile to warm my wife up to the wonderful world of miles & points.  But after a suite at the Park Hyatt DC and cruising to Key West with the top down in a Corvette, she got the picture.

I’ve had people raise eyebrows about my credit card applications or my creative  spending techniques.  They don’t want to spend the time or effort maintaining a stellar credit score or keeping track of everything!

The vast majority of my friends and family really support the madness.  People are eager to learn innovative ways to capitalize on this amazing world.  And I’m happy to help them!

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

Oftentimes I cannot find award space for flights.  I pay for plenty of flights and I always visit ITA Software to search for flights.  Their matrix is truly great and there are so many options to generate the results you want.  When you can’t find an award ticket, I would definitely make ITA Software your first website to search for airfare.

From a points side, I think shopping portals are extremely valuable.  They essentially allow you to earn bonus points for items you plan on purchasing any way!  I always am asking myself, “Can I purchase this online rather than in a store?”

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

During our honeymoon I took advantage of a Hyatt Diamond Challenge.  Doing so granted us Hyatt Diamond Status for a two-month period.  I booked many Hyatt nights during the honeymoon on points.

I had also signed up for the quarterly promotion offered by Hyatt.  Somehow, we ended up scoring an upwards of 40,000 additional points during the honeymoon and Platinum status WITH NO PAID STAYS.

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

Since I turned 18, I have always had a credit card.  I just wish I would’ve known that credit card applications only temporarily affect my credit score.  I would’ve signed up for many more credit cards at this point in my life.

I also wish I would’ve put more emphasis on hotel points.  I should’ve known that someday staying on Aerobeds or pull out couches wasn’t going to cut it!

What would your readers be surprised to know about you?

I honestly don’t travel as much as I’d like.  When you live in an awesome place like Bend, Oregon, you think twice about leaving.  Trying to coordinate vacation time with my wife’s job makes for tough travel planning.

Dovertime - Interview With Kyle

Myself in front of the golden gate bridge

Any parting words?

Follow travel blogs like Million Mile Secrets and Dovertime to help learn tricks to earn miles.  Let us do the dirty work and teach you which products we believe are the most valuable.  Use social media like Twitter, Facebook and Instagram to keep up to date on deals.  Leave us comments on our blog posts and interact with us.

But most of all – HAVE FUN!  This hobby is meant to be fun.  Whether you burn your points at Park Hyatts across the globe or at a local Super 8, I care not!  You are the only judge of the value you’re getting out of your points!

Kyle – Thanks for sharing your thoughts on having Big Travel with Small Money!

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20 responses to ““Instead, we chose to road trip the USA!”

  1. Always like these guest posts that remind us to dig deeper. I recently ordered several things on line and completely forgot to use a shopping portal. Can you hear the sound of me kicking myself?

    You did not mention why you were looking for something that rhymed with “Dover”. Can we assume that is your last name?

  2. @Anne I hate that feeling. It’s such a sinking feeling when you know you leave points on the table! I’ve definitely learned from my fair share of mistakes over the years.

    As for the name, my last name is indeed Dover! I’m glad you enjoyed the interview and hope that you enjoy reading Dovertime!

  3. How did you get the 40,000 Hyatt points without actually paying for any stays? Did you take advantage of the promotion they have going on right now? Or did you transfer them in from elsewhere?

    Also, is the Platinum status permanent or will it go away at the end of the challenge?

  4. @Rachel – I honestly don’t know how I made the 40,000 points. I signed up for the Diamond trial offer and had Diamond status while we were on the honeymoon. So I was awarded points as a welcome bonus for each stay. I bought a water or two each night from each hotel and charged it to the room. Maybe that is how I earned points. I honestly have no clue, but I wasn’t going to ask questions.

    I had enough “qualified stays” that I earned Platinum status for 2013. Unfortunately, I won’t have enough stays in 2014 to retain the Platinum Status.

  5. @Kyle – Love the idea of the road-trip – well done!
    Just get the Hyatt credit card and you can keep that Platinum status going! 🙂

  6. What a nice interview. Love it.

  7. @Charlie – I’m holding out for that Hyatt credit card!!! I guess Hyatt is far and above my favorite hotel chain to stay at and I want to make sure I sign up for the credit card when two nights will really come in handy (Park Hyatt NYC maybe?!?!).

    The Platinum Status doesn’t really do much for me other than a bonus point here and there on a paid stay, but it’ll be nice to have once I get the credit card for sure!

    By the way, I love your blog! I check in daily through Boarding Area!

  8. @Kyle – thanks for reading my blog! I am glad you enjoyed it. I look forward to following yours as well.
    You are right – Park Hyatt would be a nice one to save it for! We always used our certificates at the Andaz 5th Ave (which actually takes very good care of Plats – we received upgrades to suites each time). I only wish the PH NYC had been open :(, but the Andaz was also great!

  9. @Kyle a couple things,

    AWESOME job on the road trip. My wife and I just did one from FL to CA last year and it was awesome! Second, how do you like Bend, it’s on the list of places we want to visit/potentially live :). We love the outdoors and it seemed like a nice place.

    Thanks for sharing!

  10. Hi Kyle,
    You mentioned that you have had a credit card since you were 18. Do you have any suggestions for a first credit card? My sons are 18 and 20 but I’m still paying their bills. Perhaps it’s better to just get an additional card from one of my existing cards?
    Thanks to you and anyone else that can help!!

  11. @Charlie – Absolutely my friend! My wife and I didn’t make it to the Andaz on our honeymoon unfortunately. We opted for the Hyatt 48 Lex (which was just as expensive and cost 7,000 points less per night). I’m jonesing for the opening of that PH NYC. I honestly believe it was a small driving factor in Hyatt creating a 7th category!

    @Greg – Thank you! I hope enjoyed the content and will continue to read Dovertime and MMS of course!

  12. @Joseph – Great to hear from you! Stay tuned for a massive honeymoon recap (long overdue) on Dovertime! As for Bend, I grew up here and was lucky enough to land an amazing job out of school here! The sun shines about 300 days/year here which is so important to me! If you ski, then come in the winter and ski Mt. Bachelor. The mountain has incredible amounts of skiable terrain! My favorite time of the year is early summer or late summer. I can officially say that I’ve snow skied, golfed and hiked in one day (during June). There aren’t many places that you can do that! For places to stay we have some options with Hilton, Marriott and IHG (if you are looking to use points 😉 . If you have specific questions, feel free to e-mail me and I’d be happy to answer them! Thanks again for reading the MMS interview and Dovertime!

    @NYCuws – Your question is a very important one and it is strongly related to personal finance. In my opinion, I like seeing kids build their credit from a young age! 18 worked out perfect for me. Although I wasn’t charging too much on the credit card, I was slowly building my credit history. I haven’t canceled that card as of today as it’s my longest standing line of credit (which is very important in the makeup of your credit score). The only regret I have is applying for an annual fee credit card. Today I don’t use the card near as much (it’s the Alaska Airlines VISA), but I don’t want to cancel it because I’ve had it for so long!

    Although I don’t know your kids interests or travel goals, if I had kids your age, I would have them apply for the Chase Freedom! There is no annual fee, they just bumped the signup bonus to 20,000 points and Chase points are really valuable in my opinion. When they’re ready for another credit card, they can apply for a Chase Sapphire Preferred. At that point you’ll be able to transfer the Freedom points to the Sapphire account and REALLY squeeze some great value out of those credit cards!

    Just my two cents, but the younger you can start building that credit, the better!

  13. Thank you, Kyle!!

    I appreciate your great feedback and guidance.
    Chase Freedom sounds perfect!

    Happy Thanksgiving!!

  14. @NYCuws – Absolutely and same to you!!!!

  15. Great interview!
    However, the constant misuse of “I” when it should be “me” is frustrating to read in an otherwise well written and intelligent article. Example, “miles would take wife and I to Tahiti…” Wife and ME! Take “wife” away. You would never say “take I to Tahiti”. Also, photo captions have the same mistake.
    Sorry to point this out, but it is such a glaring repetitive mistake in an otherwise stellar posting.

  16. @TahitiSweetie – I appreciate the grammar lesson! I clearly majored in Accounting…not English!

  17. Ironic, I discovered points in Bend Dec. 2012. Got a cheap room at the Marriott there and decided to ski Bachelor for the 1st time since I live in PDX suburbs and was missing the snow for Christmas since I’m from Utah. They offered me to sign-up for their rewards program so I figured why not…. Then, they sent me a credit card ap. I am now a devotee to Marriott. I never paid attention to airline cards cause I have a family and figured it couldn’t be useful with so many people. I have long collected points, but the sluggish way and used them for gift cards. I’m not unhappy I did so, but now I know better and enjoy this new hobby.

  18. @J – That is a great story. Bend is a great place. I always say that I wish I could live in Bend and then have the PDX airport about an hour away from the house. RDM is a great little airport, but the lack of options and more expensive airfare make flying in and out of RDM a bit cumbersome.

    Bachelor’s big opening is officially next Friday (weather pending of course). Keep up the good work on miles and points!!!

  19. Daraius,

    I just wanted to say thanks again for featuring the interview! You’re an inspiration and I can’t wait to see what the future holds!

    Kyle

  20. Amen for Bend, we live there, too 🙂