Ultimate Planner or Spontaneous: What Kind of Traveler are You?

I have commitment issues. Always have! Runs in my family. It could be as small as what to get for lunch and as big as finding a home to live in. I contemplate, over analyze and contemplate some more. It’s not necessarily that I can’t commit, but more that I want to make sure I’ve covered all my options before making the right decision. The grass is greener sort of thing. It’s exhausting!

Sometimes I just can’t stand to be me. For instance, let’s take my favorite topic – travel. It takes me forever to decide on a hotel – comparing every last detail – that many times I’ve missed out on staying somewhere I ultimately would have preferred because I was spending too much time “thinking” about it and lost out. This summer we’re planning a trip to Spain, and we still have yet to book because in the back of my head I’m thinking, “is this definitely where we want to go, out of all of Europe?”

Because of my twisted thoughts, we tend to be last minute vacation planners – some people call it spontaneous – and it got me thinking, what type of traveler is everyone else? Are you a way-in-advance-planner, or do you sometimes wing it? Both can have their perks, as well as their downfalls.

The downfalls of being a spontaneous traveler are obvious. The good hotels and home rentals book up, flights can be astronomical, tours sell out, you can’t go the exact dates you originally had intended to. But sometimes last minute travel can be quite beneficial. Flights can be found for low last-minute offers (though this is more bound to be in your favor if you’re traveling solo and not with a family), hotel rooms open up for a better price than before, last-minute vaca package deals are a steal.

One of my friends texted me a week before New Year’s and said “Do you want to go to the Dominican Republic with me? I just found a $1000 all inclusive package (at a good resort for 5 nights!)”. I know a family that booked their vacation to the islands last year three days before going.

And this past summer, though it was Maine and not the islands, we booked a last minute trip to Bar Harbor and Acadia National Park, which turned out to be one of our most favorite vacations of all time. Last year I had undergone knee surgery, as I recently wrote in my post Skiing: Love it or Leave It?, and I wanted to wait to book our trip to make sure my knee would be ok for all the hiking. What’s the point in going to Acadia if you can’t hike. Though it was no 5-star resort, we found a deal at a hotel on TripAdvisor, where the room was quite a bit less than it had been a week prior. Bar Harbor is incredibly popular in the summertime, especially late August when we went, so we felt we had lucked out.

The abundance of properties in rentals like Airbnb and Home Away make it a lot easier to book last minute travel as well, a given. This summer we found a fairly last minute Airbnb on Cape Code in Osterville, when our accommodation plans changed, and last winter we booked spontaneous ski weekend plans the entire winter through! Great Barrington and Stockbridge in Massachusetts were just some of the places we were able to enjoy, including over Presidents weekend, a notoriously difficult time to find last minute rooms or homes. It goes without saying, these companies have been a huge asset to travel, for so many reasons.

But of course, as I mentioned, last minute travel has its downfalls, especially if you’re traveling afar or overseas, or to a popular destination. I had to use points (which I like to save for further afar destinations) to book our annual Naples, Florida trip this year because I was too late in the game (for good reason though – we were planning on going later this Spring, but now we’re going to New Orleans then, so I had to move FL up). Florida in February last minute is nearly impossible to book. A few years ago, we had to fly into an airport three hours away from Naples because I was on the fence of which dates we’d travel. Never again!

I was also looking into flights to Colorado for this February, where my whole extended family will be, but at $1000 + to fly into Steamboat Springs, that was not happening. Had I planned much earlier, it would have been possible. But hey, I’m happy to be going somewhere warm anyways. And for two summers in a row we went to Italy, to cities such as Rome and Venice, as well as the Tuscan countryside, where we visited idyllic town after idyllic town, and there’s no way that trip would have happened without serious planning. To get a house like the one in the lead photo does not happen overnight! Obviously the bigger trips, especially when abroad, need much time and planning. (Note to self: I am booking Spain this week).

But it’s interesting – when I think about our travels – how we’ve wound up in the situations we have, all due to timing. It can go with you, and against you. Sometimes, as with all of travel, it may just depend on how the tides flow. This year, however, I don’t want to take any chances, and one of my New Year’s resolutions is to stop thinking, and start planning! Lord help me.