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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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29 Comments

  1. Ah, yes, indeed hindsight is always 2020. . . but it sounds as though you have a great plan for your future trips. Looking forward to reading about them.

    1. Grand Cayman is a great cruise stop – 7 Mile Beach is pretty amazing! I think a 30 by 30 travel goal sounds wonderful!

  2. I love the attitude of looking backwards in order to look forward! I think when you travel a lot, maximising any opportunities to reduce costs, such as enrolling in loyalty programmes and paying attention to how to maximise points / miles is so worthwhile. I also like the idea of travelling more by land and sea, with the flip side being less air travel. Something I need to work on.

    1. Agreed! I love train travel 1 it’s my favorite way to go! I just wish we had more availability where we live. Happy new year!

  3. Great idea to plan six months’ travel at a time! It sounds like the perfect balance of planning that still leaves you open to unexpected opportunities. I’m going to give that a try myself!

  4. I really need to organize to take better advantage of reward programs. (Of course, I say this every year and wind up barely remembering them.) If you find a way to make better sense of them, let us know!

  5. You were very ambitious to plan out your travels a year at a time! 6 months too, and sometimes I can manage that, but most of the time we plan very spontaneously 3-6 months out max. Here’s to traveling better and learning from past mistakes! #FeetDoTravel

    1. I wish we could be more spontaneous but we don’t have a major airport with a ton of flight options, so we have to look for advance deals. The struggle is real!

  6. Your travel plans sound exciting! I’d love do a Caribbean cruise, in 2019 we’ve done one cruise in Europe, but I’d really love to enjoy the blue waters of the Caribbean in 2020/2021!

  7. You are wise to look at the last year with an eye to what you can improve in your general travel planning. I’ve been using points to fly for years, but I need to get better at using hotel points. I tend to save them too long! Last month we had an AirBnb that was not okay, and we ended up using hotel points mid-trip. They were a lifesaver!

    1. I have never used points to fly! Tell me your secrets!!! I’m sorry about your Airbnb experience… I just don’t think they are for me so I’m sorry to hear you also did not enjoy a stay of yours.

  8. Yes, I have eased up on long range planning too. As schedules change, so does availability and what seemed like a good idea 6 months ago doesn’t necessarily fly in the new environment. I have become more and more short term and have reaped the rewards in special last minute deals that shave heaps off the budget.

  9. We are trying to be more flexible this year as well and just take advantage of deals as they come. So we have no idea where we’re going this year yet. Which is a big stretch for me because I am a major planner. #FeetDoTravel

    1. Oh I suffer too much from tripaphobia to not have anything planned at all…. the fear of not having any trips planned!

  10. Love the idea of booking 6 months at a time. I usually only plan one trip at a time, meaning I often leave it too late to get the good deals. I’m definitely planning on being more organised in 2020 so that I’m more clear on where I’ll be going when!

    1. We have limited flight options and oftentimes they get more expensive as time passes so we have to plan early. But there is such a thing as too early too!

  11. I know what you mean about missing out on great travel deals because you have over-scheduled. Hubby always plans at least a year in advance. It means we always get the accommodation, flights, seats, tours we want but it does take away a lot of flexibility for grabbing last minute deals.

  12. I mostly plan for 3 months in advance and this means its a trip at a time. Whenever I plan a year in advance I end up changing the plan for some reason or another, its never cast in stone. Will explore your idea of booking 6 months at a time and see how it goes.

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