Patreon Gift of Cruising Winner Updates

Hello crew!  Some very exciting updates for you all here from our previous three Gift of Cruising winners.  Winner #1 has bought a boat!  And you’ll get to the see the make and model and learn why they chose the boat they did.  Winner #2 is getting ready for another round of ASA training.  Winner #3 is preparing to set sail on an offshore Andy Schell voyage.  WHOA.  And Winner #4 could be YOU on an offshore passage of your own on s/v Libra.  I hope you find these stories as inspiring and uplifting as we do.  It’s amazing to see real people, just like you and just like us really going for it.  Join the cause!  Get inspired and get on board by becoming a Patron and helping us create cruisers out of you at  Thanks to all my Patrons who have made these gifts and stories possible.

#93: Cuba Voyage Finale: Gulf Stream Crossing and Landfall in Cuba

The current of the Gulf Stream is no joke, particularly when it is pushing you into head winds.  Watch as we reef up and cross a pretty kicked up sea state across the Gulf Stream, sing to our first Cuban sunrise, deal with an issue with the furling gear on our headsail, navigate the entry to Marina Hemingway and make landfall in Cuba.  HaveWindWillTravel is traveling this year!  There’s a great Patreon update for you as well in here as we will soon be getting a video update from each of our previous Gift of Cruising winners and get ready to give our 4th gift away — a 100% free offshore voyage on SailLibra at the $500 reward level.  WHOA.  Become a Patron to be eligible to win and help us create cruisers out of each and every one of you!  Hope you all are enjoying the journey to Cuba.  We can’t wait to share that beautiful, culture-rich country with you.

Sail with Us to the Miami Boat Show!

Very exciting video for you here guys.  Our 4th Gift of Cruising will be a five-day offshore adventure sail from Pensacola to Miami with us on s/v Libra to attend the Strictly Sail Miami Boat Show, boat show tickets included.  Super cool, right?  We will depart out  of Pensacola February 10th and sail to the show.  I will be speaking at the show (so you can come heckle me!) and Libra will be IN the boat show so you can come walk the docks, tour her and meet Phillip and I while you are there.  We will give this gift away at the $500 Patron reward level — help us make this happen by becoming a Patron and emailing me to let me know you are available during the passage dates and you want to go on an offshore voyage.  In addition, if you would simply like to go ahead and book this passage to make the trip with us, feel free at!  We would be excited to have you!  Thank Captain Ryan with SailLibra for this generous donation as well as my many Patrons who make these Gifts of Cruising possible.  Get inspired.  Get on board.

Also, because it is the season of giving, I put together another full-length video for you all on the channel in our Boat Tours section.  It’s my first motor vessel tour!  I didn’t even know Gulfstar made motor yachts, but this one was certainly impressive.  Twin Perkins diesels, a generator, water-maker, 500 gallons of fuel, 250 gallons of water and insane amounts of storage.  Thank Phil for the tour of his 1979 Gulfstar 44, m/v After Five.  I blame all Video Annie comments in the outtakes on the wine he kept feeding me while I was working!  Enjoy the tour!

Gift #3: Offshore with Andy Schell

Who wants to go offshore? If you said yes, then get on board with our 3rd Gift of Cruising — an incredible offshore voyage giveaway with Andy Schell and Mia Karlsson at Here’s the deal. Since this is SUCH a big gift, Phillip and I need your help. First, watch the video (particularly Andy’s contribution explaining the sometimes uncomfortable, frightening but enlightening experience that an offshore voyage can provide), check out his FAQs, become a Patron then EMAIL me and tell me you want to be eligible to win this prize.

Also, because this is such a tremendous gift, Phillip and I need your help to fund the entire giveaway. Andy has graciously agreed to discount one of his totally-worth-it $2,500 voyages $500. We will match him by donating another $500 and I will give that away (a $1,000 voucher toward an offshore voyage with Andy Schell) regardless of whether we meet our Patreon goal. BUT … I would love to give the entire voyage away. Andy and I have done our part. It’s time for you all to come to the table, donate just a little to get Phillip and I at our Patreon goal of $500, so we can give away the entire voyage to one lucky Patron. Let’s do this!

Please send a big thanks to Andy Schell for partnering with me on this by checking out his incredibly candid and educational sailing podcasts, photos, blogs and videos at

Our 3rd Gift of Cruising giveaway (of either the $1,000 discount or ** let’s hope ** the entire voyage) will occur Nov. 4th at the latest because I’ve already got my 4th Gift lined up.  There will be no lolly-gagging here!  Phillip and I love doing this and we have a passion to help more people realize a more rewarding life on the water.

Get inspired. Get on board at

2nd Gift of Cruising Winners: Hallie and Joe!

We’re giving it away! Our second Gift of Cruising, a 6-day bareboat charter course through Lanier Sailing Academy in Pensacola, Florida goes to lucky Patron Hallie Heuser (pronounced “High-zer” she let me know) and her awesome boyfriend Joe.


We’ve got a fun message from Hallie & Joe that they sent to us for when they come this October from Madison, WI down to Pensacola, FL for the Lanier course and a day-sail on the one and only s/v Plaintiff’s Rest (yowza!) as well as a fun video Hallie made for Joe from when they got their boat (a Hobie 16), fixed it up and took it out for their first sail. Enjoy!

Thanks to my many Patrons for making this possible and who are currently helping me select my next Gift of Cruising so, like Joe said, Phillip and I can share our excitement for sailing and inspire more people to get out there and do it, too. Get inspired and get on board on Patreon.

Our New YouTube Trailer!

There she is: “Get Inspired. Get on Board!”  Please let me know what you think and, if you can, please help support our cause!  We hope this will help us reach and help more people out there like you who have the dream to cruise.  Thanks to all who have followed and supported so far.  It means a great deal to Phillip and me.

Curious about cruising?  Come aboard.  At, we’re creating cruisers, one dreamer at a time by sharing our story through books, blogs and videos, touring boats and giving away “Gifts of Cruising” (currently a 6-day bareboat charter course) to help people just like you who have the dream to cruise.  Life’s too short.  Don’t miss the boat!  Get inspired and get on board on Patreon.

Ch. 2: “No Gloves”

“No gloves,” she said.  “Okay?”

We were at Yannick’s house, meeting his wife and children, and discussing, for the first time, the realities of Phillip and I serving as crew aboard his catamaran for the passage from Florida to France.  It was pretty much understood that Yannick had granted our request to make this passage with him, but I think (wisely so), before that decision was officially announced, he and his wife wanted to sit down with us and have a serious discussion about the voyage so they could get a better sense of who Phillip and I are and why we really wanted to make this passage across the ocean.

Can’t say that I blame them.  I’m sure they were asking themselves:


I believe Yannick got a sense early on that Phillip and I were capable, committed sailors and this was truly a bucket list item for us, something both of us had wanted to do for a long time and that we were planning to do in the future on our own boat, but that Yannick’s crossing had presented itself at an opportune time to give us the invaluable experience, first, serving merely as crew as opposed to Captain and First Mate aboard s/v Plaintiff’s Rest.  Another concern Yannick had was that I would probably want to share the entire voyage on YouTube via my platform.  While he has plans to launch a YouTube channel someday, exposing himself, his family and their future home aboard s/v Andanza to the scrutiny of my YouTube audience through the perspective of my camera lens was not something he was comfortable with.  It may come as no shock that not everyone enjoys having their lives and home put on widespread public display.

While I was a little surprised and disheartened by his request initially, as with many things that appear to be bad at first, with a little time and perspective, I found it was really for the best.  It was Yannick’s request and agreement to allow me to share it on a non-public, exclusive medium (Patreon) that inspired me to create a new, hybrid platform, where some content is free, some is for purchase.  It’s like putting on a free concert, but also selling backstage passes for those who want to pay to get backstage to meet the artist.  Overall, in exchange for the privilege to be invited as crew for my first ocean-crossing, it seemed a small price to pay.  I also had a fantastic time sharing the voyage through my “Cross the Atlantic with Me” Patreon campaign via the Delorme tracker link as well as weekly travel logs, photos and videos while we were underway and I gained many new followers and supporters, whom I now call friends.

With the YouTube issue settled the only other matter that seemed of utmost important to both Yannick and his wife Clothilde, was that we understand that Yannick was the Captain.  We were to offer input and our opinions as needed or solicited, but it was Yannick who would make the decisions and instruct us accordingly.  It was Clothilde, actually, in broken English, who really drove this matter home when she said:

“No gloves.”

Clothilde previously worked as a flight attendant with France Air and was telling Phillip and I the procedure and delegation of duties for her and the rest of the flight crew as an analogy to what we should expect while serving as crew under Yannick, and she repeated the phrase several times throughout: “No gloves.”  At first Phillip and I weren’t quite sure what she meant by it but as she continued to explain, it became clear she meant no kid gloves.  Clothilde was trying to prepare us for Yannick’s very matter-of-fact, direct approach.  He was not going to sugar coat anything for us and he was not going to treat us gingerly to avoid potential hurt feelings.  If he disagreed with our recommendation or input, he was simply going to tell us, without the gloves.

“Agreed,” Phillip and I said in unison, both surprised by Clothilde’s bluntness and both in admiration of the no sugar-coating agreement Yannick and Clothilde had obviously assumed in their relationship which had served them well for years, as they have embarked together on many adventures—sailing, traveling, moving from France to the states and back, as well as biking and backpacking through Iceland, and much more.


With those understandings in place, it was understood.  Yannick was the Captain and Phillip, myself and Johnny Walker would be joining him as his diligent and dutiful crew.  One other very exciting piece of information we learned during this meeting was our departure date:

May 28, 2016

Why was that exciting?  Because thirty-four years ago, on that date, a fine specimen was brought into this bright, blazing world.


Annie “Jo-Lo” (2) and “Bro-Lo” (5) circa 1984.  Anyone remember ShowBiz Pizza Place?

When I learned we would be leaving on my thirty-fourth birthday, I knew, then and there, I had made the right decision.  I couldn’t imagine a better way to celebrate the accomplishment of thirty-four years—particularly when I had spent the last three trying to build a life that allows me to do the two things I love most: write and travel—than by setting off on my first trans-Atlantic crossing, my first trip overseas to Europe and my first blue-water voyage.   As Johnny so accurately put it: This trip was going to cross “many items” off the bucket list.  But, it was mid-April already so we had much to do to prepare for the trip.

Very soon after mine and Phillip’s “no gloves” meeting with Yannick and Clothilde, Yannick set up another rendezvous at his house, when the whole crew was able to attend, for a detailed discussion about gear, provisioning, sail plans, weather and (most importantly) crew safety, complete with a slideshow he had prepared.

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I kid you not.  Yannick had put together a very helpful step-by-step PowerPoint that he used to walk us all through the important topics that needed to be covered to ensure we were all aware of the risks we were taking, how to decrease them and how to respond if we did, in fact, find ourselves in an emergency situation.  I was astounded at the amount of research, thought and energy Yannick had put into this trip.  Well, except for the meals.  I give you Yannick’s thoughts on passage food:

Aside from meals, however, he had considered and made contingency plans for some situations I had never even considered.  When we were discussing that night the one obvious downfall of the crew—i.e., our lack of experience in that not a one of us had crossed the Atlantic Ocean before—I will never forget what Yannick said when I made the comment that, despite his experience, I believed he was competent and intelligent enough to serve as our Captain for the passage.

“It’s not intelligence,” he said.  “It’s situational awareness.”

Touché.  I could tell at the outset I liked Yannick.  Was he cocky at times?  Sure.  He’s a fighter pilot.  They all are.  Well, most of them.  (Allan, if you’re out there and reading this, I exclude you.)  Was he blunt and dismissive of input at times?  Yep.  But, it was often because he had already researched, considered and (rightfully or wrongfully) rejected your idea.  Frankly, I like that quality in a captain.  If anything, he was decisive and incredibly efficient in the use of his time and resources to analyze, decide and move on.

“No gloves.”  Got it?


Got it.

I have uploaded a link to view the entire, extensive PowerPoint slideshow our esteemed Captain put together for our first crew briefing on Patreon.  You will see there were many (many!) situations of which he was more than aware.  : )


In the PowerPoint, Yannick mentions a “2012 Passage Video” aboard s/v Andanza.  This was something super cool I shared on Patreon back in May.  Get this: Andanza has crossed the Atlantic Ocean not once, not twice, but THREE times before we set off on her in June for her fourth crossing.  And there is an awesome video on YouTube from the previous owner’s crossing in 2012.  Check it out!


Did you SEE the 17.4 knots she was making?  I believe the highest our Niagara has ever reached was 8.3.  (Phillip, correct me if I’m wrong on that.)  And, that was while surfing down a wave.  At the time, I could not fathom a sailboat traveling at 17 knots.  I can now …

With our extensive crew de-briefing complete and all crew in agreement with the “No gloves” standard operating procedure, all that was left to do was (snap our first crew photo!) then ready the boat and crew for the passage.


We were about six weeks out from our departure date at that time and we had about 600 very important things to accomplish before then.  First and foremost, our focus was on the boat.  We only needed to install and test a few key items before we would be ready to shove off on May 28th!

  1. The mast
  2. The new sails
  3. A few windows
  4. Some critical transmission parts (which were still en route from Italy ETA TBD at the time)

Minor stuff, really …

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(Screenshot from my first tour aboard Andanza, posted to Patreon May 4, 2016.)

I hope you all are enjoying the Atlantic-Crossing tale thus far!  You’ll see there is a lot of additional Patrons-exclusive content I have been posting to Patreon since we learned we would be making this voyage back in April.  If you needed any other excuse to get access to some extra goodies, I hope a chance to win our 6-Day Bareboat Charter Certification course through Lanier Sailing Academy is enough!  Just a few short weeks before we’ll be giving this awesome prize away.  Get on board at

Gift 2 logo

Gift #2: 6-Day Bareboat Charter Course!

Gift of Cruising Campaign #2 … LAUNCHED!  I’m giving away a 6-day live-aboard Coastal Cruising and Bareboat Charter course through Lanier Sailing Academy in Pensacola, FL this October which will (of course!) include a tour of our Niagara 35 post-shipyard and a day sail with Phillip and I aboard s/v Plaintiff’s Rest.  If you were ever waiting for a reason, this is it.  Become a Patron for a chance to win this awesome prize.  Giveaway date is 8.12.16!