Here’s How I Burned 2,791,500‬ Miles In 2019, How Did You Stack Up?

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Some guys are great at recording all of their trips and the value of each mile burned. I’m not that precise, but I went back several years, tracked down my flights taken, and posted them on DDF for 2009, 2010, 2011, 2012, 2013, 2014, 2015, 2016, 2017, 2018, and 2019.

In 2019 I burned through some 2,791,500‬ miles and points. As my family grows I find it easier to burn through miles quicker than ever.

Don’t cry for my miles though, I’m still sitting on 8 figures of unredeemed miles and they’re not earning any interest just sitting there. If you have them, use them! Learn more about earning miles from credit cards in this guide and about the Chase Quinfecta earnings machine here.

2019 flying map and routes:



Here’s how I burned them:


  • I flew from Cleveland to Newark on United, Newark to Toulouse on a Gulfstream V, Toulouse to Miami-Opa Locka on a Bombardier Global 6000, and then back from Fort Lauderdale to Cleveland on JetBlue. Sometimes the best trips don’t cost any miles at all 🙂
  • Our family of 5 flew from Cleveland to Maui via Chicago in United 777-200 lie-flat seats, from Maui to Kauai on Hawaiian as a free stopover, and from Kauai to Cleveland via Denver in United 757-200 lie-flat seats: 500,000 United miles.
  • 5 nights in 2 rooms at the Fairmont Kea Lani Maui: Free with lifetime Platinum status
  • 5 nights in 2 rooms at the Grand Hyatt Kauai: 250,000 Hyatt points (including 1 Globalist night at 25K value)
  • I flew from Cleveland to Los Angeles as a day-trip with several friends for KWFE LA: 25,000 United miles.

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Not a bad way to fly across the pond! #PrivateJet

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#A380 #First

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#Paradise #Kauai @grandhyattkauai

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  • Our family of 5 flew for Shavuos from Cleveland to Tel Aviv via Newark in United 777-300 lie-flat seats outbound and 787-10 lie-flat seats on the return: 750,000 United miles
  • 3 nights at the Ritzaliya (Ritz Carlton Herzliya): 150,000 Marriott points (including 1 Ritz night at 50K value)
  • 5 nights in 2 rooms at the Waldorf Astoria Jerusalem: 760,000 Hilton points

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  • I flew from Cleveland to Fort Lauderdale on JetBlue to go to my nephew’s bris and flew back from Miami to Cleveland using Platinum card airline fee credits.
  • 1 night at the Residence Inn Surfside: 25,000 Marriott points (in the form of a credit card free night)
  • I flew with my grandfather from Cleveland to Toronto on Air Canada to catch a Tribe game together: 25,000 United miles
  • 1 night at the Westin Harbour Castle: 35,000 Marriott points (in the form of a credit card free night)






  • I flew with Mimi from Cleveland to Newark for a friend’s wedding: 26,000 Avianca Lifemiles
  • 2 nights at the Park Hyatt NYC: 54,000 Hyatt points (after 10% points rebate)



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Full link to story in Bio. Some people love shopping for souvenirs when they travel. We have a different philosophy and love having a professional photo shoot. We found Jonelle from @waileaphotography back in 2011 when we flew to Hawaii with 5 month old Rafi. We loved how she captured the spirit and memories of the vacation and had her take our photos for on many more trips. It’s never easy to get kids to cooperate for a photo shoot, but Jonelle did an amazing job getting them in the mood for pictures. She had a passion and huge talent for her craft. Sadly, I just learned that Jonelle battled with depression and it wound up claiming her life. Obviously that’s not something a professional discusses with their client, but I just wish I had the chance to say something that may have changed that outcome. It says in Koheles that he who lives should take it to heart. I hope that if anyone reading this is going through turmoil in their own life that they speak to a professional as quickly as possible before making a decision that can’t be undone. And so, farewell Jonelle and rest in peace. We will certainly miss you and your bright spirit. Your incredible work will be found on the walls of our home for years to come.

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  • I flew with Mimi from Cleveland to Chicago on our anniversary as a day trip: 26,000 Avianca Lifemiles



How did you do in 2019? Hit the comments below and make your own map to post on DDF.

Here’s to a fun 2020, follow my trips in Instagram here!

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43 Comments On "Here’s How I Burned 2,791,500‬ Miles In 2019, How Did You Stack Up?"

All opinions expressed below are user generated and the opinions aren’t provided, reviewed or endorsed by any advertiser or DansDeals.


I’m more curious to know how you earn your miles.


Also interested to know!


Ditto and yes I am… but that many so fast… for me to get to one mill is a major feat


Referrals, when you click on a credit card offer from this site he gets 25000 points on average, probably more on most


it’s amaze me that you could enjoy all of this with your family !
happy for you !


Nice Dan!
1. How did you find availability for 5 on the ORD – OGG I space,,,dont think ive ever found an upgrade on that route and we take it average once a year.

2. You always find the most amazing looking food (and i’ve tried your picks in some restaurants , were usually as described). How Many calories did you burn in 2019 lol


No travel since August?!

How much spent in annual fees total?


Hey Dan,
I noticed that you still have your Fairmont lifetime platinum status. How did you get them to honor it? Who do I call?


He paid for it.

Unless you paid for it during the promotion years ago, I don’t think calling anyone will help.


What I want to know is how much you needed to pay out of pocket to rack up those miles


I have a good way to help burn miles-
Have a raffle for all your dedicated readers….

P.S.- If anyone asks, it was Itchakadoozie’s idea (Wink, cough, eh hem…)


I would like to know, how many miles did you accumulate in 2019?

Chezky B.

How did you manage to find 5 available round trip award tickets to TLV for shvues?


Nice post!! Happy for you and your family.
Iv been on this site since 2016 and have accomplished many things that were once just a dream thru opening up cards…although on a much lower scale;)


It’s fairly easy to earn a miles. With AA / Hyatt link etc , points rebates, hybrid redemption etc etc Even when you are redeeming you generally get rebates.


hey, you are the guru after all! its only befitting for you to accomplish this.
beautiful post! and beautiful family B.A.H!

David Smith

Nice! What a year. Enjoyed reading. Thanks for sharing. And your site.

Would be interesting to see a similar post about how many miles you accumulated this year and approximately how you did it. If you wanted to share that! Good stuff.


What’s plan C,D,E

Greta Thunberg

How dare you?




Bravo! And I’m jealous with a capital J.


Sooo cool! My fave was seeing you pitch at the World Series (or something) with SPG moments.


Check out DDF. And read more posts I’ve written….what is DDF?


DansDeals Forums


Ive been following and trying to do as you say but no where near 8 figures. Maybe you can do a seminar in Brooklyn to help us? By the way Im Non profit so the maaser on those miles you can donate to me!

new yorker

Majority of miles is thru spending or new cards?


How did you get 2 rooms at the Waldorf over shavuos at the saver rate?

Mark A

Dan. I’ve been a fan of yours for about 13 years . You are awesome . I have learned much and have enjoyed many adventures on a dime. How did you manage that private flight to and from Toulouse ?

Thanks many blessings to you and yours in 2021.