I Should Have Been On That Boat

“There it was, headed out the Pass, and I wasn’t on it.  I should have been on that boat.”

I had a follower tell me this recently and it really resonated.  He was watching the “Where Are You Going?” video I published months ago when I first announced our plans to cruise south this coming season to the Keys, perhaps Cuba, Isla Mujeres and a dozen other potential places and I mentioned a particular moment that was, for Phillip and I, a significant “kick in the rear” to make us really decide to go cruising this year.

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It was the inaugural Pensacola to Cuba Race October, 2015.  Phillip and I almost had the opportunity to crew on a boat that was making the voyage but─for many reasons, mainly life got in the way─we weren’t able to make that trip.  I still recall the feeling Phillip and I both had as we watched dozens of boats sail right by us and head out the Pass toward the Gulf of Mexico.  It was regret.  We both wanted to be sailing south along with them and it was soon after that day that Phillip and I decided the time to go is “now” and we started making real plans to go cruising this coming season.  The Cuba rally jump-started us.  It lit a fire, one not even the unsettling discovery of our rotten stringers and the three-month stint we put in at the yard readying our boat for blue water, could put out.  We are sailing south this season.  Nothing will stop us.

Apparently my video jump-started my follower Matt, as well, when he saw in my photos from the rally the very boat he was going to crew on for the Pensacola to Cuba race, the s/v Libra, a stunning Tripp designed 60′ ketch.

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You see, a similar thing happened to Matt.  Matt also received an invitation to make this trip on the gallant Libra but what happened?  Life got in the way.  He told me he couldn’t finagle the time off from work and, for that reason, he had to pass on the opportunity.  For him, my video served as his “kick in the rear” and he said, “Never again, will I miss that boat.”

Cheers to that Matt!

Matt’s story struck me on many levels.  First, his message reminded me what I do all of this for.  I work incredibly hard, every day, to put together this whole HaveWind production and it makes it all worth it when just one person reaches out and tells me my message has had an impact.  A very smart man once told me the best measure of success is how many people you impact, so Matt is proof of my success today.  But, I also found myself lavishing every word of Matt’s story because it is currently my own.

Friends, I have some incredible news to share.  I have been offered a once-in-a-lifetime opportunity, and I am excited and thrilled that I have worked so hard to take control of my career so that I make just enough money to cruise by doing what I absolutely love (writing and creating) that I will be able, this time, to take advantage of it.   The “Libra” sign is represented by scales because it means everything is in balance, and I feel because my life and career and passions are finally balanced out─in that I work to live, not the other way around─is the reason this opportunity presented itself at this time.  I’m not only going to take advantage … I’m going to seize the hell out of it!

This time, I am going to be on that boat.

I will soon be setting off on a passage.  One not many people and not many sailors make in a lifetime.  In June, I will board this boat and cross a body of water I have not yet faced.

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All will be revealed in Friday’s video.  I hope you are as excited about embarking on this adventure as I am.  Life is incredibly full for this little sailor.



10 thoughts on “I Should Have Been On That Boat

  • In the video, which is terrific, there is a picture at 4:44 of a boat behind the Tripp 57, Libra. The rig is very distinctive. Looks like the Bruce King designed and Brion Reiff built 40 footer on which I raced in Maine, Wind Rose. Does anyone know the name of the boat in the video? I couldn’t find a suitable entry in the race documents. The original owner died and the boat was sold. Would love to know where she is and that she has a good home.

      • I have been looking up the race and it looks like a good one. Almost as long as the Bermuda Race. A rough ride, too. I think it has the legs to become a classic. Norm

      • Hey Norman. It is! A great race, although it was a terrible ride this past time. Four boats turned around after facing three straight days of unexpected weather and one boat was dismasted! Hey, wanted to let you know I reached out to the owner of the Tripp ketch in the video to see if he knows the owner of the Bruce King you asked about. More to follow.

    • Hey Ryan! So glad to find you here. Matt’s been a fun follower to have on board. I was really touched by his story about not being able to be “on that boat” with you. Like I said, never again. I’m about to get on a boat and go on an incredible adventure. Announcement to come tomorrow so stay tuned! If you like to read, Ryan, I’m happy to send you free Kindle copies of my sailing books. Just say the word. Enjoy all the fun sailing content on the website. I had a follower ask me about the boat behind you in the race. He thought it was a Bruce King designed and Brion Reiff built 40 footer named Wind Rose. Do you know?

      • On the cubarace2015.com website there is a list of entrants… I looked but didn’t see wind rose. Though the name may have changed. The list is there.

        @Anniedike we are headed back to Havana in 4 weeks, come go with us!

      • Hey Ryan! Ooh, wish I could and thanks for the offer. But, in four weeks, I’ll be embarking on my own once-in-a-lifetime passage. All will be revealed here tomorrow. Stay tuned!

        Next time Havana! : )

  • Thanks Libra and Plaintiff’s Rest! I have read the reports and it looks like a hard ride. That’s ocean sailing. You have to buy a couple of those snotty day tickets before you can buy a perfect week ticket. Wind Rose had a very unusual sail plan which is just like the one behind Libra. that’s what got me wondering. Maybe it was a high roach main on a catamaran? Anyway, good job on the race down. I did the St Pete Lauderdale Race in 71 and it was th coldest worstest sail I had ever experienced. The Gulf is not placid. Averisera out

    • Agreed Norman. We’ve had some of our worst sails in the churn factory down south. While I haven’t crossed an ocean (yet), the Gulf is no joke.

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