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2013 Whitby Brewer Rendezvous

You may remember it was only 5 months ago that I was scared to death to take my boat in and out of the marina for fear of crashing into everything. Like, everything.

I was reminded of that the other day when I pulled the boat into the marina, kicked it into reverse at the end of the fairway, spun it 90 degrees, backed it 75 yds straight down the chute and landed perfectly in the slip without touching a single piling. Without even thinking about it.

I was tied up, walking towards the restaurant before I noticed the family of 5 staring at me. The dad said “As you were pulling in, I told my family to watch because I thought for sure you were about to crash. I can’t believe how easy you made that look!”

For the last 6 months, I’ve slowly, one day at a time, been figuring it out. You’ve heard me say it before, but I wasn’t born knowing how to sail. I don’t have a trust fund, a secret offshore account or a sugar momma. I still have absolutely no clue how I’m going to accomplish my dream of sailing around the world.

But I’m closer today than I was yesterday.

There have been times when the unknown was frustrating as hell. I’d tell somebody that I was working towards #31 on my bucket list and they’d get all excited. Then they’d ask me what kind of boat I had. I’d say something like “Well…I don’t exactly have a boat yet. I’m still trying to figure it out.” and their enthusiasm would deflate, as would mine.

Then, a year ago I got the boat and everything became a little bit more real.

Since May I’ve taken the boat out nearly a hundred times. And I’ve learned something new each and every time I’ve been out.

One day at a time.

I’m fortunate in that I’m standing on the shoulders of giants. I’ve been able to learn and get encouragement from countless people. Skipper J, a guy who has owned 112 powerboats in his life, but never once a sailboat, taught me how to drive mine like a pro.

Randy has pushed me to go sailing at least once a day, no matter the conditions. When I’m looking for passengers, Sayrah and Kat have been ready to go regardless of day or time.

Mark put a date on the calendar and told us to invite crew for a long weekend sail. I invited a few guys including my dad and we shared a weekend that will never be forgotten. Incredible stuff.

The past few days have been some of the best. You may know that I have a goal to attend at least one conference a year where I don’t know another person.

This week I added the Whitby/Brewer Sailing Association’s Rendezvous to that list. On Wednesday I sat in a room with 45 other people who own, live, & sail on boats just like mine, picking their brains and learning from their experience.

Then, Thursday, I was able to attend the Annapolis Boat Show; something that’d been on my to-do list for years. Walking around the soggy show, trying to stay dry, I had the chance to talk to many of the leaders in the industry. Inventors and designers of knives, magazines, anchors, and even boats.


Several of you have asked for an update as to how my plans are coming. As you know, in July I stood on a stage and told 2,800 people that I was a year and a half from departure. I think that’s still fairly accurate.

This winter I plan to perform a few upgrades to the boat (i.e. replace freshwater plumbing, install refrigeration, etc.). Next spring/summer I plan to sail the boat as much as possible and then spend next fall/winter performing an extensive refit before a winter/spring 2015 departure.

There’s been a lot of interest in the curriculum aspect of the trip. I think I’ve finally decided on a distribution model. I’m not ready to go into details yet, but I’m really excited about it and have a much clearer vision for what it’s going to look like than I did a few months ago.

One day at a time.

Stay tuned.

Bo is currently living in Orange Beach, Alabama working towards checking #31 off his bucket list. If you’d like to be a part of the adventure, consider sponsoring a mile. To get more info on the curriculum, sign up here.

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