First things first. Let’s be clear about a few defining details related to my personal travel style.

I am a planner

I am not someone who can just quit their job on a whim and jump on a plane going to the first place I think of the next day. I won’t go into all of the boring details, but I ultimately had over six months from the point in time when I decided to leave my company and my last day at work. I was fortunately able to be very transparent with my manager, CEO and team so we could work together on the transition with plenty of time to find my replacement.

I also had lots of time to formulate a plan for my travels. I needed a vision, I needed a roadmap, I needed an agenda. It became clear that I was going to tackle this year like it was my job. Which, I suppose, it was going to become (although it unfortunately wasn’t going to pay me a salary). If I was going to invest a year of my time at a stage in my life when my earning potential was nearing its peak, I needed to ensure I got as much value out of it as possible. I surely wasn’t going to sit around sleeping in and watching Netflix (as wonderful as that sounds).

For numerous reasons that I’m not going to get into here, I chose March 1st as my target last day at work. I then started to think of numerous places I wanted to go. Bucket list types of places and experiences, with the sky as the limit. Then I started to research the best time of year to visit and formulated a rough itinerary for March-December, with the first few months in a lot more detail than the later months. Being a planner, I know that nothing ever goes 100% as planned. And having worked at startups for most of my career, I know that you have to be comfortable with ambiguity and ready to pivot if your original idea isn’t working as well as you’d hoped or if market conditions change. It’s good to have some wiggle room and to stay open to going with the flow. But it’s always important to start with an idea of where you want to go. The fun part is then figuring out how to get there.

I am not a budget traveler

I don’t mean to be obnoxious, but it’s just the truth. I don’t need to always stay in the most luxurious hotel or fly in first class (although it certainly can be nice), but I’m not interested in staying in hostels or only flying dirt-cheap budget airlines. I’m willing to pay more for convenience and comfort, and there are times when I will splurge on an amazing experience, five star hotel or business class on a long flight (within reason).

That being said, I certainly play the points game. I just prefer to maximize the value of points to upgrade my experience in cases where I otherwise may not have been willing to pay cash. One example I am excited about in my upcoming year:

• Park Hyatt Tokyo – Consistently one of the top-ranked hotels in Tokyo, and also the setting for the film Lost in Translation that I loved in college (and will need to watch again before my visit!)
  • After a quick scan, I found that Hyatt.com was listing an advance purchase rate of $1,028/night during the time I plan to visit (late March/early April, hopefully perfect timing for cherry blossom season).
  • By transferring Chase Ultimate Rewards points to World of Hyatt points, I was able to book three nights at the Park Hyatt for 90,000 points (30,000 points/night). Yes, that may sound like a lot of points, but those 90,000 points are only worth $1,350 if I were to book travel directly through Ultimate Rewards. That’s an additional $1734 in value that I found and now I get to stay in an iconic five star hotel and re-live scenes from a film that I somehow still own on DVD.

Finally, I am a huge believer in loyalty programs

Delta and SPG have both been very good to me over the years (I have Diamond status with Delta and Platinum Premier with SPG/Marriott). There are few things that have made me as giddy in my adult life as a surprise upgrade to Delta One after getting stranded in Madrid overnight. The upgrade to a three bedroom/three bathroom, multi-floor suite when spending five nights at the Sheraton Grand in Cabo for a friend’s wedding wasn’t too shabby either.

Back to my plan for the year

The initial itinerary I developed includes ten months of travel across twenty countries and every continent except for Antarctica. It’s a mix of eco-tourism destinations, cities, beaches, wine country, culture and more. I am hoping that friends and family will meet me for some of the time, but I expect that I’ll be flying solo for much of the year. I’ll be staying at luxury hotels, bed and breakfasts, eco-tourism lodges, AirBnBs, boutique hotels, ryokans, glamping tents and who knows what else. We’ll see how it plays out.