We Set a Date!

OMG we finally did it! We set a date!!!

I write this both excited, and utterly afraid. This coming August we’re leaving the Thames River Yacht Club for the last time in our lives. We’ll cross Lake St Clair on day one and overnight at a sister Yacht Club in Lasalle, Ontario. Day two will see us headed East into new territory – Lake Erie hopefully making Buffalo, New York by the end of the first week. From there, it’s traversing the historic Erie Canal and then finally pointing Lady K’s bow south for the first time ever.

We intend to pop out in New York and tour Manhattan for a few days before heading into the great Atlantic Ocean only to stop in Chesapeake Bay for the Annapolis Sailboat show in October. We’ve been to this show a few times by car but one of my dreams was always to go in my own boat. One smaller dream crossed off the list in the chase toward the biggest dream, a dream I have been stewing over for at least ten years. All the planning is finally making sense!

From Annapolis we head to Florida and in early November, we cross to blue water – the Bahamas.

The general goal is the British Virgin Islands but like anything in sailing or dream chasing, plans are written in sand.

My heart is full of passion thinking about this stuff. But there really is so much to do.

We’ll be moving aboard K again this spring just like we did last year, but this time we’re getting rid of the house completely. This means of course we have to sell everything we own. That’s where I start to get scared. Talk about commitment! Move aboard May 1st and have literally nothing to go back to. No house, no beds, no furniture. The garage is full of tools that have to go, couches, cars, a motorcycle. The list is endless. And once it’s gone, there truly is NO TURNING BACK!

We’re keeping summer clothes, some boat applicable tools, and that’s basically it.

People are starting to worry and ask questions so hopefully I can cover some of the big ones real quick.

  1. What will you eat? It may seem silly but we are actually being asked this and the answer is fairly simple – we’ll eat whatever the locals eat. Food is a worldwide commodity so we don’t imagine we will have much trouble with that. We will have to learn how to fish though. We suck at that.
  2. How will you live without income? This one has been in planning for a long time. Truth be told, it’s my single greatest worry. However we will have 10-20k saved along with money from stuff we are selling (insert shameless plug: anyone want to buy a couple of convertibles and a motorcycle?). From there, I will be a certified Marine Surveyor and can still do computer repair, web design, and whatever other labour work I can find if needed. Candice is a seamstress and is bringing her sewing equipment. I think we’ll be fine.
  3. How will you Wifi? This is a big question but we have a solid plan. We need Wifi to keep you guys up to date with social media and of course we will continue to make Lady K Sailing videos along the way. Our good friend Mark helped up build a high gain Wifi Antenna which will be perched atop our 45 foot mast (thanks Mark!). We expect a range of several miles and have been testing it in the garage at home with promising results. We should, fingers crossed, be able to grab open Wifi signals from anywhere on land within a few miles. Think fast food places and local free hot spots. This is then rebroadcast in our boat with a standard Wifi router.
  4. What about health care and dental? Well, we imagine doctors and dentists are fairly universally available and we do have some money and credit cards if things really get bad. We’re both healthy and are getting anything we need done before we leave. Aside from that we plan to have a pretty good med kit with antibiotics and other regular things just in case.
  5. How long will you be gone? I always say “Forever” but as I said – written in sand. We want to see all of the Caribbean islands but also may make our way up toward Italy and cruise the Mediterranean for a spell. The UK isn’t impossible either. Honestly, we don’t really know for sure.

All that said, we want to live a life of adventure and experiences instead of a life of “stuff” and chasing dollars. Does that make sense?

We wouldn’t have made it this far without a team of awesome friends and family, as well as those who have sailed this route before us. We aren’t reinventing the wheel at all. We take our inspiration from people like the crews of Delos, Windtraveller, Sailing Uma, and others. This life truly is something any one can do and we feel blessed that we get to take you all along for the journey.

I have honestly never been so scared in my life, but as Ralph Emerson said: “Always do what you’re afraid to do.”

Wish us luck


As always, anyone who want’s to help please consider supporting us on Patreon. You can commit to a couple bucks a month to help us chase the dream and of course, Patrons get early access to new videos and some other perks.

Love Tim

Lady K Sailing

2 thoughts on “We Set a Date!”

  1. Wish you luck with all your dreams and destinations, so cool. I hope to follow you through all your posts, its really exciting. Your in for the adventure of a lifetime!

  2. A bit early for Good Luck, Bon Voyage or Pleasant Sailing. I do wish you Fair Winds & Friendly (not calm… you gotta have some fun) Seas.
    I look forward to learning of your adventures and will miss having a good friend around.
    Maybe we will see you back some day.

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