Posted in Travel Planning

Are you a Tortoise or a Hare when making Travel Plans?

I find that there are 2 styles of travel planners, the Tortoises and the Hares. 

The Hares don’t give as much though to travel down the road and focus mostly on the trip at hand.  They often make quick decisions or last minute arrangements.  Hey that can be a great way to snag some last minute deals.  They don’t fret about using their points/miles for whatever opportunity comes up or focus as much on long term travel goals.

The Tortoise is methodical and takes their time planning things out long before their trip.  They research deals, look for the best ways to use their points and sometimes create a strategy for how to earn those points.  Some Tortoises are even working toward multiple future trips.  It’s like chess in that they have to make sure they have all the pieces they need to attain the goal they want.

The Hare

Up until about a year ago, I merely dabbled with some Loyalty Memberships but had never really gotten into the big game of Points/Miles.  Back then, I had no idea that you were supposed to assign a value to your points so that you got the most bang for your buck when using them.  If I had enough points for a Reward, I would redeem them not really knowing if it was a good deal or not.  I just figured if it was a Reward purchase so I had done well and saved some money.  I was the “Hare” when it came to travel plans, earning and burning without a real long term plan.


Transforming into a Tortoise

Wow!  The difference a year can make in how your mind thinks about these things.  I now follow tons of Travel Experts, reading and learning from them daily.  I am now trying to be more of a “Tortoise” when planning travel and making strategies.  I started looking down the road last fall toward a big trip I want to take to Portugal in September of 2020.  That is a long term goal.  I know I want enough hotel points to cover most of the rooms on our stay (so I have been hoarding hotel points) and I hope to have enough points to fly Business Class through ANA on one of their carriers (which required me to sign up for a new card that earns Membership Rewards points).  The Tortoise approach lets me plan the steps I need and have time to earn the points required for when the time comes.  So I have this future trip to work toward but have also been planning and taking other trips in the meantime.

Unfortunately, before my conversion to the life of Travel Points/Miles, I did not set myself up very well for some of the plans that were yet to come.  During my time as the Hare, I signed up for a local bank credit card, made some credit card account upgrades and later opened a couple of new Travel cards that I thought were a great idea at the time. When you are working with Chase, who has a lot of great Travel Credit Cards, they have a 5/24 rule.  If you have opened 5 credit cards (of any kind) in the last 24 months you can’t open a new Chase bonus card.  What I needed was a Chase card that earned Ultimate Rewards, but found myself over the 5/24.  Now I have to wait until one of those items passes the 24 month window and falls off before I can make that move.

This was one of the hard ways that I learned being a Tortoise is better for making travel plans and strategies than being a Hare.  I can achieve more travel by strategizing my travel plays, and I will make better decisions as I learn even more about the rules and nuances of the tools available to me.


A Win for the Tortoise

One of my best successes this year was planning a trip to Hawaii for my husband and I for October.  It all started from a flash deal from Southwest Airlines to sign up for their card to earn 30,000 points and a Companion Pass for the year.  I almost let this one pass but it was just too tempting. For just a moment I let my inner Hare take over and made a split second decision to go for it.  I knew that I needed to fly with a Companion at least 3 times this year to make it worth the 5/24 slot with Chase.  Once I qualified for my Companion and bonus miles in March, I booked a trip for my daughter and I where she was my Companion (trip 1).  My husband and I knew we would be going to Texas in September (trip 2).  One trip to go to make me confident that I had made the right choice.

In March, Southwest announced they would begin flying routes to Hawaii.  When Mark and I were considering possible destinations, Hawaii made it’s way onto our list.  We started to get serious about it so I priced it out.  Turns out I could book the entire 4 segment trip using only points!  I even managed to get our Early Bird Check In Fees covered by Airline Credits and Travel Erasers from other cards. I am pretty proud of myself for making this work.  Even though signing up for the new card was a total Hare move, planning out how to make the most of the offer was a total takeover by the Tortoise.

With 4 months until the trip, I have started to make a plan for how to cover at least some of the cost for our lodging.  A work in progress for this Tortoise!


Final Thoughts

Everything is really about finding the perfect balance.  Sometimes an awesome travel deal  or credit card offer pops up and you have to jump quick like a bunny to snatch it up.  But for most travel, I think taking the slow and steady planning approach of the Tortoise gets you the biggest win!


So, are you a Tortoise or a Hare?


Dream, PLAN, Save, Adventure!


Just an Art and History Nerd from MI Who Loves to Travel, Explore, Save Money, Share Tips, Enjoy the Best Foods & Adult Beverages🍷🥂🍸 Then Blog About It!