To do the plan you presented - 3-4 days learning,come back for 3-4 days sailing I would contact the charter company that rents the type of vessel you are interested in for a bareboat - and ask them to provide a teaching Captain the 1st trip and try to learn enough to take the same boat out again for your return visit.
This all totally depends on your starting point on the learning curve - if you are starting at zero sailing but solid boating experience there should be no problem qualifying as you can always drop the sails and motor but if your total experience of boating is limited it may be hard for you to feel comfortable handling a good size vessel with only 3 or 4 days of practice - navigation, docking, anchoring, even picking up a mooring are skills that do take a bit of time to become familiar with.
Remember bareboating was started to allow people who owned boats or were experienced boaters the opportunity to sail in other waters without bringing their own boat - unless you have a Captain and or crew it is not strictly a vacation type event - But sailing lessons are fun and a wonderful way to see the islands.

I suggest the week with FWS. I sailed a bit about 20 years ago, but on smaller boats. I did the FWS course about 2 years ago and have since chartered 3 times. All the charter companies that I know, want to know your experience and certifications. A 40' monohull is a $150k+ investment and they want to make sure they get it back w/o incident.

Rules of the road and MOB drills are stressed at FWS. But they allow for relaxation time. A week goes very quickly.

Jayne:

The Mrs. & I are ASA Bare-boat Certified. This consists of classroom & hands-on instruction. Two 2 day courses and a 7 day sail with instructors for the Bare-boat Cert. Some companies do the Bare-boat portion in 3 days after the initial two courses....but we felt more comfortable doing the 7 days.

Charter companies usually require the bare-boat cert or a resume indicating training/experience before renting you a sailboat.

Also, you will be liable for any damage done to the boat.....even if you take the insurance ($500. deductible), if the insurance company determines that you "over-stated" your experience level you might not be covered at all....thus you will be required to pay 100%.

Sailboats in the 40 foot size cost anywhere from $250,000. and up....plus the cost for loss of revenue.

Suggest, if you're not experienced, charter with a Captain first. Spend a couple of days doing this, get comfortable and come back for your certification later. Don't rush it.

F.I.

Thanks for all the good advice! I hope I didn't give the impression that we wouldn't have the utmost respect for the owner or charter company. We completely understand the investment in these vessels. We've heard that you can report more experience than you have and manage just fine, but we would NEVER do that.

Future Islander, I particularly like your suggestion about not rushing this experience - for safety and quality of the experience, I'm sure. This is a good reminder. I think we started to approach this activity like a career goal and we need to remember that, "hello, we'll be in the islands!"

A couple more questions for Future Islander and everyone:

Are there any recommendations regarding a Captain who is qualified as an instructor that would be willing to take us out for just 2-3 days before we do an ASA certification course? Or should we just contact a company like The Moorings to connect with someone?

Which companies do the bareboat portion after the initial two classroom days - separately? The only reason we haven't booked with Fairwinds is because we're personally opposed to the week long schedule. It will work better for us to break things up into separate portions. Even if we extend our trips to 10 - 12 days, we want to be sure we do a few days in a villa so we can visit our 'usual' favorite spots before we return home each time. Plus we usually travel with friends that do not boat and it would be nice if we can still spend a few days with them.

Thanks again!
Jayne

Jayne:

Sorry, we took our initial 2 courses in NJ.......then the NJ Sailing School sponsored a 7 day bare-boat course in the BVI's....it was great!

You do not need to take the bare-boat course from the same company as the initial 2 courses.

Perhaps someone else could provide suggestions in STT or the BVI's.

How about taking the initial courses where you currently live?

Also, after you get certified......the U.S. Coast Guard Axillary gives a good "advanced navigation course"...it cost me $60. plus study materials (approx. $40.) for an eight week (once a week) course.

Have a good time sailing!

Visiting the BVI's is a good starting place for new sailors......lots of islands, restaurants, coves, etc.

F.I.