Sailing around the world.. Literally

This is how it all started. Like many of you, I sit at a desk all day and wish I was on vacation or at the least out of this cubicle hell. I have carved out a pretty comfortable life for myself. I do computer work. Specifically I work with Citrix, which is a whole subject in itself. Citrix is a platform that many very large companies require but there isn’t a whole lot of people at my level that can do it in their local markets. So for many years I was a road warrior and was able to go to most large cities and work for 6 months or more. It was like an extended working vacation. Each place I integrated with the locals and found all the cool places and things to do. This really rekindled my love of travel that I missed from my time in the Navy.

Back to cubicle HELL. I was flipping through some social media page when an article about a lady who gave up a lucrative job, sold all her belongings and now lives on a beach serving ice cream. The point is she lives on the beach and gets to live that life. The life I long for. So I thought; what is really stopping me from doing that now. I already wanted to retire at age 50. So why wait that long, why not do it now? Well the main answer is I have a wonderful 15 year old son who lives with me full time and is a freshman in highschool. That gives me time to plan. Now I have 3 years to plot and plan and make my escape. I already have a zombie plan of getting a sailboat to get out of town. (More of that later) Now I just need a plan.

Ok here is my plan, it is pretty ambitious and I have no idea if it is going to work or if I am going to really be able to do it but… I want to step foot in every country before I die. Now I know I could fly but anyone who knows me knows how super cheap I am so I want to sail to as many places as I can. In my travels I have knocked out many places and I don’t typically like to go to a place twice when there is so much of the world to see. I will also need to make money while I am on this trip. Since most beaches don’t need a computer guy I need to find another option.

Problems with my plan. (and possible solutions)

I don’t have a sailboat – This is a pretty big one but once I retire I have 3 years to find one and either finance or sell off all the things I have aquired over the years. I am really looking for a Catamaran as I like the speed and shallow drafts.

I have no idea how to actually sail – I have purchased some books and plan on taking classes to try to learn. I also purchased a Hobie Cat but that has been a disaster.

I have no idea how to fish saltwater – This I have really been working on over the past 2 years. I have purchased a center console sail boat and have been learning how to boat fish but really need to understand why certain fish bite when and what to look for if I go to a new place.

I will need to make money  – The toughest one by far. My current plan is to do what I love which is dive and snorkel. I have made it through Open Water, Advanced, Intro to Spearfishing, Nitrox and Rescue Diver and have been overcoming my natural fear of the water. I grew up watching Jaws so I spook myself pretty much every time I am in the water. I hear Duuh dummm.. So I have to calm myself down. So on my travels when I go diving I like to talk to the Divemasters and see where they have been and realized that is my solution is become a Divemaster. I have recently found out that the military will pay for the rest of my classes to become a full dive instructor.

If I figure out all these issues I can execute my plan which is start in the Caribbean and work through all those islands. If Cuba economics are what they are projected I may never leave there. Back to the plan. Once I hit those and all the way to French Guiana I will sail to Panama City and go through the Canal. Also a lifelong dream. I will hit all those down through Chile. I am concerned about making that point around Cape Horn to get to the Falkland Islands but I will do much more research before then. Once I get past that I want to get to the far east tip of Brazil and head towards Africa. I want to work my way south around the southern part of Africa and go through the Red Sea. I will make my way up through Egypt to the Mediterranean Sea and really explore that whole area.

So there it is; the ultimate adventure, bucket list, before I am too old to enjoy it, life plan. I want to set out a timeline and tell everyone about each step of this wonderful adventure I call my life.