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So here is the big question …. How to TRAVEL like a BILLIONAIRE? In less than a year I was able to earn Medallion Status with Delta Airlines. I want others to know how simple it is to achieve this and so much more!. This is not an ad. This is not a commercial. It’s my real life. By using specific cards in conjunction with your planned trips for 2024 or even 2025 and beyond you can rack up a slew of miles and use them for free flights, upgrades and even Dom Perignon! < – – – YES! That happened at the Delta Sky Club in LAX. I was able to have my first sip of Dom thanks to a few miles that I had in my account! This was back in 2018!

This is the part where some will shame you for what you do with those points and miles once you earn them. I think as long as it brings you joy and maybe to a new place that works for me! This is also the part where people will disagree with what card or cards you should be using. This brings me back to my first 2 points. As long as it brings you joy and maybe to a new place that works for me! There are a few things I think you might want to know before you go off and apply this but that’s just me. The Chase 5/24 rule, what is a referral link and thinking that annual fees are not worth it just to name a few. I started my travel hacking journey back in 2009 when I had an American Airlines Citi Advantage card. I used those points to fly from Chicago to Los Angeles in May 2009 when my grandfather was admitted into hospice. I originally booked the flight to come home 4 days later but after talking to the airline I was able to keep an open ended ticket and come back after my grandfather passed. This allowed me to spend almost 2 months with my family and the flexibility to come home when it was time. I have booked so many flights with points and miles since then I have lost count. I have also used them to get my favorite magazine subscriptions sent to my house. The best advice I can give to someone just starting this journey is research, research, research! I can not say it enough, I have learned some mistakes the hard way myself but I have also seen the mistakes others have made and then shared with the community.

My trip to the Maldives -

How did I book it?

At the time I had the American Express Platinum and the Gold cards so combining those sign up bonuses and points I earned when it was 10x on grocery for the first 6 months. I transferred my points to Aeroplan with Air Canada to book my flights. I booked 2 one way tickets vs a round trip ticket since I had already had about 70k in Aeroplan. Looking back now I wish I would have done a little more research and possibly could have found something better with another airline transfer partner. Also most of the flights I booked were either cancelled or had to be re-booked because of the changes. When I tried to check in online it wouldn’t let me and that was a total headache with Etihad telling me I needed to talk to Aeroplan about an Etihad flight to get my seats assigned. I also didn’t want to be on a flight for 15 hours in economy. I survived because I bought myself an emergency exit row seat for $163.75 USD. Then on the way home I had to fly 4 different legs to get here. This is what I mean about my flights being changed to something completely different from what I booked in early January 2022. For my longest leg I was already seated in Premium Economy. I paid $122.52 extra for the other 7 hour flight from Abu Dhabi to London to be seated in a preferred bulk head seat.

For the hotels I paid 150k points per night for the Waldorf Astoria and 120k points per night for the new Hilton Amingiri. You also have to pay for a boat transfer to each location. The Waldorf was $899 and the Hilton was $300.

What did I spend on this trip: $1020 at the Waldorf and $700 at the Hilton

Both of those totals include all of my boat transfers, food, drinks and activities during my stay. At the Hilton they have a resident artist and activities that you can make your own souvenir with sea shells and sand. I also did a snorkeling trip that was the highlight of the whole trip. It was $75 plus the taxes and fees (22%) that brought it to $92 and then I tipped the crew because they were fantastic.

Of all my flights the Air Canada leg where I was seated in Premium Economy was the best! Its their version of business class and they served a full meal with glassware.


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I hope to outline some strategies that have worked for me and help others in the process. Here are a few questions to get you started:

1. What is your closest airport? What airlines service it?
2. Domestic or International travel?
3. Do you currently have any cards that earn you rewards?
4. Do you know how much you spend per month in expenses?
5. Do you have a dream vacation already in mind?

If you want to email me the answers to those questions I would be happy to set up a Zoom call to discuss your options and some ideas! TOR@TRAVELlikeaBILLIONAIRE.com