Where do we start? What’s the plan? How is this all going to work out? Can we afford that? It’s all a bit too overwhelming to handle.


It’s easy to feel in over your head when it comes to traveling. Or even when it comes to living life without a general direction.

The questions and options can seem endless.

So how have we stopped ourselves from spiraling down a dark hole of anxiety? We did the opposite of what most people would think to do.



Sure it isn’t as simple as just those three words, but it’s close. We often find that when making decisions, when it comes to life or to travel, people get all caught up in the planning.

In our world of technology, we have a wealth of info at our fingertips. We could plan every trip down to a “T” by reading through the plethora of websites and every guide books out there. But spending your time sifting through a million websites is not going to get you the perfect trip, it is going to leave you feeling conflicted with options. Everyone out there has an opinion to share, how do you know which one will suit you, your needs, your timing, your budget, your desires!?

Of course, you want your trip to be the best possible. You don’t want to finish your trip and after-the-fact feel like you missed out on the perfect hot-spot because you hadn’t done your research. Why wouldn’t you! You’re investing your time and money into this destination, you want it to be the absolute best.

We’ve been there. We live a life of travel, of non-stop destinations. We don’t want to sail away from a country and be kicking ourselves later that we didn’t see such-and-such. But we have found that the over-planning was just causing us more stress.

You can have a general idea of a plan, but to plan down to every day, every minute, that’s just no fun.

Half of the fun of traveling is the people you meet and get to share your travels with.



It’s happened that we set out sailing thinking we were heading in one direction, but then we crossed paths with a boat that was perfect for buddy boating with, and BAM, whatever plan we had was down the drain because now we were sailing off to where ever these cool cats were going.

We have also found ourselves living in the Virgin Islands for most of the last two years because of the people we have met. We have made great friends here, and they have made our island experience so much more fun, without them there would be islands just like many others. They were worth diverting our plans for.

Don’t stress about having a lengthy plan, chances are you won’t stick to you and you will have just wasted all that time in creating a said plan.

I have a friend that planned the most fun get-away for her son’s birthday. They were taking off, just the two of them, they would hit up Disney, Legoland, and his favorite restaurant. Can you guess what happened after all the planning and money had gone into getting the tickets? Her son had enough of theme parks after one day and wanted to stay at the hotel pool for the rest of their trip!

The art of travel is to learn flexibility.



Be open with the adventures that get presented to you and your trip will be so much COOLER than you could’ve planned for.

What do you do when you get somewhere and find out about this awesome restaurant in the neighboring town, do you stick to your well-laid-out plan, or do you b-line it for this new adventure? Flexibility is key.

Take your family on that trip, but don’t get bummed if the day you had planned to tour the historical sites your littlest gets diarrhea and you are stuck in a hotel room. Roll with it, enjoy the two channels of Spanish television you have, and be thankful for hotel bars and AC! No one could’ve planned for that.


Even with our very general plans, we never seem to stick to them. Life is just too full of the “unexpected”. We have been thrown for twists and turns that have led us to buying boats, living in foreign countries, buying property in the Rocky Mountains…and that crazy list of unpredictability just seems to go on and on for us.



First off, once you have booked your trip, CELEBRATE! You are going to travel!

Buy yourself a guide book or two. Or check out a website or two (not a million). Get a general idea of the destination you are heading to. Create a general plan for yourself, but stay flexible and fill in the blanks of the trip once you have arrived.

Don’t use a plan as a “safety blanket”. Even without a plan, everything will work itself out. You will come home with some crazy stories to tell, and the exhilaration of knowing you did it all by the seat of your pants.

This lesson in flexibility not only applies to travel, but it can also apply to all aspects of life.

-A birth plan? Have a general one, but be flexible, because you certainly can’t control everything that is going to happen.

-A work plan? Sure, choose a career, but be open to changing your position as it will bring you a new skill set.

-A lifestyle. It’s what we do. I can tell you that as of right now, WE HAVE NO IDEA where we will be one month from now. When we tested the waters (by writing the blog post) to see if anyone would be interested in buying our boat we didn’t expect such quick responses. Our “safety blanket” of the boat may soon be gone, opening up many other doors and options.

Someone recently told Arias (our 7-year-old) that we are “selling the dream”, by selling our sailboat. They thought we were crazy. But just as plans change, so do people and so do dreams. We have plenty of other dreams we wish to achieve and by not having a set plan, we are open to the “unexpected” that our next steps will bring.

We are not going to overly stress about making a plan right now, because in one week time everything could change, we expect that any sort of craziness could happen. So, in our eyes, no point wasting our time making the perfect plan. Instead, I’ll use that time to enjoy where I am currently sitting…on a sailboat, near an island, in the Caribbean.