"I think I know who you are." were the very first words she ever said to me. It was impossible for me to know then, so many years ago now, how intertwined my life would become with hers and her extended family and how much this young woman named Brooklyn and her family would fundamentally alter the course of my life.

The very last words she ever sent me were "I love you." Two days later she was gone. 

I have known pain. I have known loss. But I have never experienced anything like this. It's been over a year now and echoes of her life continue to ring clearly through mine every single day. I suspect they always will.

I am a shell of my former self ... 

In July, out the blue, I got a call from her uncle Dana. Dana was the one who would fly down to help his sister Rebecca, Brooklyn's mom, take care of Brooklyn down here when things were bad, as they often were. I remember Brooklyn telling me so many stories about her uncle Dana that when I finally met him I felt like I already knew him. This was a common experience with Brooklyn. He said something to me when he first met me that to this day still brings me to the verge of tears, paraphrasing because I no longer remember the exact quote, "Once you became part of their lives I could rest a bit easier." 

He was piloting a 47' Catamaran sailboat and needed some urgent repairs and wondered, since I was in the US, if I could find a place where he could have the repairs done.

"What's Dana doing in the Atlantic?" I thought. I knew he sailed but I didn't know he did anything like this.

I did the best I could and managed to find a marina that could accommodate such a wide boat. He invited me down for dinner and I ended up staying for a couple days trying to help out where I could. Some time afterwards he sailed up to Annapolis and I joined him on the boat for five days. 

At some point, and I don't remember how the conversation even started, we were talking about how he needed to sail the boat back down to St. Martin in the fall. The next thing I knew were were talking about me joining him on this journey and I said yes before even pondering the question in any kind of detail. I would have my own cabin with a double bed and equipped with a separate head and shower. This is the lap of luxury. 

There are just some opportunities to which one cannot say no.

The summer was dark. I had big plans of finishing up the American Sailing Association courses I had started decades ago. But the darkness conspired to prevent me from getting much done. I moved as if through molasses. The months ticked by and the window of opportunity closed.

"Don't worry about it, Yermo." Dana said. "You'll learn more about sailing on this trip than you would ever learn in any course."

I have 1000 hours or so at the wheel of a power boat but less than 30 at the helm of a sailboat and only about 5 at the helm of a catamaran, namely this one. This opportunity is not one that many people get and it is not without its risks, especially given my inexperience, but again, there are just some things one can't say no to. 

There are loud voices of guilt screaming in my head. I should be working. Building the software behind this site has turned into such an epic undertaking that I sometimes wonder if I will ever get it done. "I should be at my desk here working away like I have been for so long, not galavanting off on some adventure." There are always reasons not to do a thing. There are always obligations. No matter how many times I've irresponsibly headed off into the unknown on some fool adventure, there is a guilt. It feels so wrong to go. It feels wrong to leave obligations behind. It feels wrong to be an imposition on friends who watch my place and take care of things for me as I am away. And, of course, it feels wrong that these adventures cost so much. 

But I must go. 

I confess, I didn't actually think it was real. I figured something would happen. Maybe Dana could secure someone with much more experience than I have to take my cabin and I wouldn't be allowed to go. Maybe the boat couldn't be repaired in time. Maybe he would change his mind. The same old toxic beliefs continue to plague my mind as they always have.

I just don't understand why I have been given this opportunity. It feels too big. 

It was just over two weeks ago that the reality hit me that this was actually going to happen. "We're on our way."

Of course, the stack of boxes of equipment in my living room and garage destined for the boat should have been a clear clue to me.

"Oh shit." 

Now I regret not having prepared more thoroughly. For the last two weeks I have been scrambling.

The experience so far has been an interesting one. It's been a very long time since I've been a rank beginner like this, embarking into something I know next to nothing about. We will be sailing down the Chesapeake and then probably just off the coast all the way to Florida where we'll make the short crossing over to the Bahamas where we will stay for a few days. From there it's a 1000 or so mile leg to St. Martin across what, for me, is big blue water. 

I know from my motorcycle trips that on the first trip one always over packs and there are always things that, if one had had more experience, one would have brought. Kneadable epoxy, for example, is something I always bring with me now on my motorcycle trips. The stuff is magic. I also never leave without heated gear even in the dead heat of summer. I learned the hard way things can get cold very quickly especially in the mountains. 

The other thing that happens when one embarks for the first time is the thought of what could go wrong. The mind always gravitates towards the unlikely but catastrophic. Imagine going across the country and into the distant mountains on a motorcycle. What will go wrong? What should one fear? I remember imagining falling off the mountain, getting mauled by a bear or mountain lion, getting robbed, etc. But now with dozens of trips under my belt, I no longer worry about these things. I now prepare for mechanical failures, flat tires, and making sure I stay warm enough so that my back doesn't lock up. For me, because of health issues, eating the wrong thing is the most likely problem on a long motorcycle ride.

So here I sit on the verge of an entirely new kind of adventure that I know next to nothing about. So I asked myself the question, "What do I not know?" which I could, of course, not answer. 

However, I know Phil, from the 2010 Alaska trip, who is the most accomplished sailor I have ever met. I asked him the question and he's been an invaluable source of information. I also know Lara who has also been an invaluable source of information. 

So with answers in hand I set about over-equipping myself. 

Of course, I imagine all the Bad Things(tm) that could happen. I've read about catamarans flipping, which it turns out is actually quite difficult to accomplish. I imagine going overboard. I imagine being at the helm in weather. 

But I don't know what is likely to happen that I am not imagining. 

"Staying dry is hard." is something Phil told me. "Everything gets wet." 

We'll all be wearing life vests at all times and there are safety lines run forward on the boat which we'll secure ourselves to if we go forward. I watched a man overboard video which was filmed on very quiet waters but it impressed upon me how incredibly difficult it is to see someone who has gone overboard. At West Marine it was strongly suggested that I get a new kind of gadget called an AIS Personal Locator Beacon which attaches to the life vest. The idea is that if you go overboard it deploys automatically and starts sending messages to the chart plotter and radio on the boat to sound an alarm and clearly show your position to your shipmates. I imagine making some mistake and going overboard at night when I'm at the helm. It would be good if there was something to wake people up if that happens. 

So I got three of them, one for each person on the boat. It was expensive but it seems like a critical piece of technology, a gift to the boat.

I also picked up a Garmin InReach which is a satellite messenger that enables me to send text messages from anywhere on the planet. It also shows my position on a map which I will make public and link to once we are under way so people can track my progress, or lack thereof. "At least if you bite it we'll know where." I can hear some of my friends thinking.

Will I go overboard? I suspect it's very unlikely. I figure more likely I'll fall down and hurt myself on something or some other mundane but potentially critical thing will happen that I haven't considered. You're much more likely to hurt yourself at a stoplight or gas station on a motorcycle than in some huge dramatic accident. My suspicion is that there are analogous scenarios on a boat.

"Do you know CPR and basic first aid?" a nurse I know asked me. It's been many years since I've taken a first aid course. This is another oversight. I should know more than I do.

I picked up a bunch of gear. Is it too much? I don't know.

• foul weather pants and jacket
• foul weather boots
• sailing gloves both fingerless for warm weather and cold weather ones
• good sunglasses along with, what are they called, the little things that go around your neck and attach to the glasses so you don't lose them.
• a water proof case for my phone
• water-proof compression travel bags to keep my clothes dry, because Phil emphasized how much everything gets wet. These have the added advantage of making clothes take up less space and are the only reason I've been able to pack in as much as I have.
• a collapsible travel bag
• a set of carabiner clips because Lara said these would be very useful
• thermal base layer for the cold
• hand warmers that double as charge packs. I'm not sure if this is a good idea or not. What happens if I go into the drink with these battery packs? Salt water and electronics could be bad, but I do not know.

I also got evacuation insurance. This is critical if you ever travel far. If you are injured and need to be transported back to the States for treatment it can be unbelievably expensive, so you get evacuation insurance to cover the potentially hundreds of thousands it might cost to get you back safely. This is different from travel insurance. I went with MedJet Assist which I've used before. I've never had to make a claim but I've heard horror stories. 

I also bought a few books on sailing figuring that there will likely be quite a bit of down time. 

But the most time I've spent is in configuring my notebook to use as a full on development machine so, when the opportunity arises, I'll be able to get some work done. The guilt of leaving my obligations looms large but will I actually be able to do any work? If past experiences are any indication it's unlikely.

I had pondered setting up a separate site for this sailing adventure but I'm spread pretty thin these days so I've set up a "Ride" here on Miles-by-motorcycle.com to document it.

This catamaran sailboat is a very funny looking motorcycle that floats. The whole point to this platform I've been building is to have a place to plan, track, and share motorcycle travels. It's just feels natural to use it to share the story of this trip. Weird floating motorcycle. 

There are tabs at the top of the page. The one you are on now is for the blog and once I have more articles posted there will be buttons at the top and bottom to allow you to go from article to article. 

There is a "Planning Map" tab where I keep suggestions of places to see and things to do along with our planned stops. (Do you have any suggestions of anything to see between here and St Martin? If so please let me know and I'll slam them onto the map.)

The Posts tab is just a place for me to keep notes, kind of a running stream of consciousness about the trip akin to a twitter. (Once I finally get the offline mobile app done this will become really useful.) 

The Trip Map tab contains what actually happened. It'll contain the track of our journey, updates, and photos. 

If you want to be notified when I post updates you can sign up on the site and then click Join Ride and select "Watch". If you have any problems logging in please let me know. (I occasionally get reports that people can't log in but have never been able to reproduce it ... and none of them ever respond to my requests for more information.)

I ran a last round of errands and spent the evening sitting around a fire with good friends. Tomorrow Duncan picks me up at 10 in his big SUV. We'll load up all the equipment that has been shipped to me to bring to the boat and we'll head to Baltimore where the boat is currently docked. Because of weather, the  boat may stay in Baltimore for a day or two or we may head down to Norfolk and wait out the storm there

Suddenly this is all very real. 

I can't believe this is happening.