Hindsight Is Always 2020 – Even When It Comes To Travel


2020! How is that possible? They say hindsight is always 20/20. This is true, even in the world of travel. For this new year we are looking to the past as we plan our future travels.

As I said in my post about my 40 countries by 40 goal, I don’t always think it’s important to know where you are going. But, I do think it’s important to remember where you’ve been. Again, this statement is truer than true in my life.

With that in mind, we are planning our 2020 travel year by looking back on a few mistakes from years past.

Here are three key changes we are going to make this year and in years to come:

  • Maximize points, miles, and other loyalty programs.
  • Buy more snacks and drinks at stores when we travel as opposed to always going out.
  • Plan 6 months worth of travel at a time, instead of planning everything we will do for the entire year.

In the not-so-distance past, we realized we were missing out on some great opportunities to cut our travel costs by maximizing points. It’s not that we didn’t know, it’s that we just never really looked into it. And yes… we have let points go unused. Knowing what we know now, we have made some changes in this realm of our travels.

We will also make some changes to our snacks and drinks when we’re on the road. The reasons for this are varied, but overall it’s pretty plain and simple!

We planned nearly our entire 2019 travel year in late 2018. Sure, there are many benefits to this. But, in hindsight, it also caused a few issues. First, several of the plans we made ended up falling through. Second, when we saw a great last minute deal (or two), we had to pass. We simply had over-scheduled ourselves. This time around, we have decided to plan our travel year 6 months at a time. Hopefully, this will allow us to know what’s coming down the pike, but also to jump on those last minute specials!

Now that I’ve laid out some of the changes we hope to make as a result of past travel mistakes, let’s look to the future! So where do we hope to go?

By planning 6 months at a time, we already have our first two trips of the year planned and ready to go. Early on, we are thrilled to be heading back to one of our favorite US cities to visit friends. In the second quarter of the year, we will venture to two other long awaited European countries for a 10 day tour.

Because we’ve decided to wait on planning our second half of 2020 travels, I’m really excited to see where we actually end up. There are a few “big ticket” destinations in mind already. I am hopeful to take a little bit longer of a vacation in the fall and go somewhere really special… in a different hemisphere…

We also have a few some US cities we have talked about venturing to for a long weekend. These possibilities include Philadelphia, Charleston, Savannah, Gulf Shores, or even Chicago!

In 2019, we didn’t go on a single cruise. This is something we normally do about once per year. We actually had a cruised planned for this year, but it fell through with the Cuban travel ban. So, in 2020, I wouldn’t be opposed to finding a different great Caribbean cruise to go on.

As with most years, we are pretty open to whatever travel opportunities come our way.  I’m excited and grateful we have the opportunity to get out there!

By Land and Sea

When thinking about what I’d like to do with By Land and Sea this year, the list seems never-ending.  There is so much to learn about and do in the world of blogging!  I started this blog four years ago as a way to catalog our adventures – share photos, remember details and itineraries, tell our stories, and connect with and inspire other like-minded people.  I’m excited to see what the new year brings to blogging as well!

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