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  After finding out the friend no longer maintained charter boats, I reached out to Florida Yacht Group.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!