The First Bareboat Charter

Once we were approved for a bareboat charter, we wanted to practice a bit.  Our sailing experience had been limited to older boats with standard full batten mainsails.  Our charter, a 2013 Jeanneau 41 DS, was equipped with an in-mast furling sail.  We had read about them and watched a few dozen Youtube videos, but we wanted to get a lesson on using them.  Additionally, the Jeanneau was equipped with a sail drive.  While not a big concern, a sail drive would perform a little differently than those we had trained with.   Since I was living just outside the District of Columbia, I started looking for an opportunity to get out on such a boat.

With just a few clicks on the internet I located Blue Note, a 2013 Jeanneau 44 DS that was available to charter through Norton Yachts in Deltaville, Virginia.  A quick call secured Blue Note, along with a Captain/Instructor, to take us out and prepare us for our upcoming charter.  We spent an afternoon learning the sail system, and then practiced docking.  We planned to charter Blue Note at least one more time before our November charter in Key West, but quickly arriving fall temperatures in Virginia, and a couple of ladies named Irma and Maria prohibited us from any further sailing before the big week was upon us.

After Key West was hit by Hurricane Irma, we were sure that our charter scheduled for Thanksgiving week would be canceled.  It seemed likely that we would be forced to wait until spring.  But a few weeks following the storm, we were contacted by Florida Yacht Group with news that their boats had come through the storm and all reservations were still going to honored.

lorac-00021Our charter was scheduled for November 19th through November 26th.  We opted to pay a sleep-aboard fee so that we could get through orientation and get settled on the boat the night before.  This is the only time we have chartered, but I highly recommend using this option if offered.  It gave us a chance to get settled on the boat without feeling rushed.  And, we discovered a couple of issues that needed to be addressed by our charter representative, which were addressed and we were able to cast off the dock lines early the next morning.

We picked the boat up at Oceans Edge Key West Resort Hotel & Marina and headed northeast to Newfound Harbor for the first night.  When we requested the charter, we submitted a float plan for the week.  During our pre-departure brief, we learned that some of our planned stops should be avoided due to hurricane damage that had not been cleaned up yet.  They recommended Newfound Harbor, so we made that our first destination.  Over the course of the week we anchored at Newfound Harbor, Woman Key, Boca Grande Key, and Marquesas Key.

Overall, it was a great week.  We learned a lot, and enjoyed having the boat all to ourselves.  We had mostly light winds, but it was very relaxing overall.

Securing a Bareboat Charter

When we became interested in learning to sail, our goal was to be able to charter a boat and sail it ourselves, just the two of us.  Of course, no one in their right mind was going to simply turn over an expensive sailboat to a couple who had absolutely no sailing experience.  So, that means we had to learn to sail and get some experience.  Then came a few charters with Captains, and a week-long ASA live aboard course designed to award a certificate showing competence to charter a bareboat.

While we were looking for the fast-track to bareboat chartering, I had no illusions about becoming an experienced sailor during a one week course.  But without friends with sailboats, we didn’t have a lot of opportunities to build on the skills and knowledge we acquired during the course.  We did do a couple of day-sails with a captain, and it did help.  So we decided to reserve a boat.  If they accepted us, great.  If not, hopefully we’d be told what we needed to do to get there.

Since we were originating out of Central Florida, we wanted to do something in Florida.  The Keys seemed like a good choice, since that was where we took our course.  I contacted our ASA instructor, Capt Maclean, and asked for recommendations on charter companies.  She recommended we try Florida Yacht Group, and also gave me the name of a friend in a local marina that had a couple of older sailboats available.  After finding out the friend no longer maintained charter boats, I reached out to Florida Yacht Group.

I called and talked to Jan Henry, from the charter office.  We discussed our sailing experience and whether or not we would qualify for a bareboat charter.  She was very optimistic and encouraged us to complete the bareboat charter application process and let them do an evaluation.  As a part of the application, I had to submit a sailing resume and a float plan for our trip.  She sent us all the forms, and even some samples to give us an idea how to ensure we addressed everything.

The sailing resume was extremely thin.  I highlighted the fact that I’ve been a boat owner for over 30 years, albeit 15-20′ ski boats.  And I detailed each of our sailing excursions highlighting the boats sailed, and exactly what we had experienced during each outing.  Then I outlined the sailing certifications we had received through the ASA sailing course.  ASA 101/103 for Christine, and ASA 101/103/104 for me.  We were asking for a charter over Thanksgiving and it was July, so I also listed our plans to do more sailing before our trip.

I scanned the documents and emailed them to Jan at Florida Yacht Group.  A couple of days passed, and then came the email response from Jan.

Hey Chris,

Key west charter manager wants you to have a captain…not enough sailing experience.  Whatcha got to make a case?


Well, honestly I was expecting that but had hoped to learn what we needed to do to be able to charter.  I knew we didn’t look like competent sailors on paper, but we felt we could handle a boat as long as we were careful and stayed out of heavy weather.  We might have to eventually do a charter with a captain, but it wasn’t going to happen over Thanksgiving.  And I wasn’t going to try to rewrite a resume to somehow make little experience seem like a lot of experience, so I emailed Jan back.

Hey Jan,

I don’t have a lot of experience.  Can’t get captain experience until you can get a boat.

We’ll consider doing a charter with a captain in hopes of showing our ability for future possible charters.  We’re not interested in spending Thanksgiving week with a captain.  We want to spend a week alone.  If we can’t sail, we can always get a cabin in the mountains somewhere. 🙂

Thanks for your help!


It wasn’t a really big deal.  I expected it would be a while before we’d convince someone to let us charter.  We just needed that first one under our belt.  It would come.  But, a little while later, Jan emailed back.

Hey, I just talked with the Miami Charter Manager…our boss.

He agrees with you.

So…here’s the deal…during the briefing…if you feel like “oh yikes, this is a freakin’ big boat”…a captain will be available for you as long as needed (of course, for a fee).

That way…you get experience and you’re off and running…er…sailing.


Just like that, we were booked.  Now we just needed to do our part and get more sailing under our belt before Thanksgiving!

Finding the Right Sailing Course

There’s no single method for learning to sail.  There isn’t a licensing requirement for sailing like those required for operating a motor vehicle or aircraft.  Many accomplished sailors have never had any sort of formal training.  Because we don’t have friends who sail, we were forced to look for courses or someone who could teach us.

Our first thought was to combine a sailing course with a vacation to the BVI.  We had talked to a couple of friends about potentially going with us, but schedules are hard to synchronize.  If we went by ourselves, we would have likely been paired with other students.  More students on the boat would mean less hands-on time.  Then there was a chance we would be partnered with students who had a lot more experience than us, making it difficult for the instructor to meet everyone’s needs.

Chris, Capt Jennifer, and Christine at the end of the weeklong course.

During our research we discovered Sunshine Coast Adventures out of Tavernier, Florida.  We decided to sign up for their Couples Sailing Course with Capt Jennifer Maclean.  These courses focus on teaching couples to work together to make sailing safe and fun.  We elected the 7-day course with hopes of completing ASA 101, 103, and 104.  Capt Maclean is a very accomplished instructor and has won the ASA Instructor of the Year Award 4 times.

We certainly didn’t come away as accomplished sailors.  But we did establish a solid foundation that allowed us to quickly build the skills necessary to secure a bareboat charter.  You can make the argument that ASA 101, 103, and 104 should not be combined into a single week time period because of the vast amount of information that has to be covered.  On day one, the Captain told us that we might not be able to complete it all, or that it could work out that only one of us achieved all three certifications.  She let us know daily how she thought we were progressing.  About three days in, Christine decided she was only going to attempt ASA 101 and 103.  She felt she wasn’t catching on quick enough and wanted more time to get through 103.  It worked out perfectly with me receiving all three certifications and Christine receiving ASA 101 and 103.

We had no illusions that we were ready to jump on a bareboat and sail into the sunset.  We needed more practice.  We did several day charters with Captains that allowed us to practice.  Having said all that, I highly recommend Sunshine Coast Adventures courses.  For us, it was a complete emersion into sailing.  We cast off the dock lines on Monday morning and returned to the doc the following Sunday evening.  We anchored each evening and got a great insight into living on a small boat.

We completed the certifications in June 2017 and were able to secure a bareboat for the week of Thanksgiving out of Key West.  We were very confident and had a fantastic time.  We are confident we could secure a bareboat charter with any charter service now.

The Spark

I had always had an interest in sailing, but growing up in northeastern Alabama on a shallow lake didn’t afford many opportunities.  I did spend time on the water, and have owned three ski boats and still have a 19′ Arriva ski boat with a 150 HP outboard.  A little over a year ago, Christine and I went on a cruise to the Bahamas where we spent a few days in one of the many resorts.  While there, we took the opportunity to get a quick lesson on a Hobie Cat and we were hooked.

Upon returning to work, my boss was also returning from vacation.  He and his brother and their families had charted a 54′ sailboat in the British Virgin Islands.  Tom and his brother had grown up sailing with their father, and are both accomplished sailors.  I immediately started researching to learn all I could about acquiring the sailing credentials needed to charter a bare boat.

Before we made the significant financial investment in a sailing course, we thought we should hire a boat to take us sailing in a real sailboat.  Christine signed us up for a 2-hour sailing orientation on Lake Monroe, in Sanford, Florida, through U-Sail of Central Florida.  We wanted more, and since we knew we wanted to sail offshore we needed to find someone to take us offshore.

We stated looking for charters online.  After research, we contacted Captain Hendricks of Sailing Winsome Sailboat Charters in Daytona Beach, Florida.  It was a beautiful, but blustery day, with winds gusting 20-25 knots.  We left the Intracoastal waterway through Ponce Inlet with gusting winds out of the east as the tide was going out.  Seas were 5-8 feet, but Captain Hendricks and his Pearson 365 was up for the task.  Again, we knew this would not be our last sailing experience.

It’s Only Money, Right?

On February 13, 2018, we became sailboat owners.  There’s a 1998 Pacific Seacraft 40 sitting on the hard in Annapolis, Maryland, just waiting to be moved to Daytona Beach, Florida.  We’re in the process of changing her name to Ella Mae, and setting Centre, Alabama as her new hailing port.  There are stories behind it all.

As the tagline says, we came to boat ownership by the seat-of-our-pants.  We read and researched looking for “the right way” to become sailors.  As with most things, there are no rules, and no single “right way”.  We’ll share our experiences to this point in future posts, and bring you along as we move forward.

Welcome!  Thanks for joining us!