This question is almost embarrassing.....

Tom J · Feb 20, 2019

It might be okay to head down Biscayne Bay, away from ship traffic, etc., on a fairly calm day, and raise the mainsail. Try it out with the wind on the side, and behind the boat. Get a feel for how the wind fills the sail and how it moves the boat. Take it easy, and take it slow. If it gets a bit windy, or the waves are a bit sporty, there is nothing wrong with hanging out at Key Biscayne with a cold one. Might be best if a friend who has sailed is with you.

Gunni · Feb 20, 2019

He can buy a 41' sailboat but he can't afford an instructor? Wait till you see the dockage and maintenance costs for that boat!
Try this link

shemandr · Feb 20, 2019

You should spend some money and get someone to help you learn how to maneuver the boat out of and into the dock under power. Maybe you've done that. After that you could go out to a relatively uncrowded area with adequate depth of water in fair weather and pull out some sail. The Hunter will sail reasonably with just the main. So pull out about half (I assume it's "In Mast Furling" for the main) and drift around for a few hours. It may be dull but you won't know how much you're learning. The major thing to watch for is turning through the wind with the wind from behind the boat. That will cause the main to flop across the boat and fetch up hard. If the wind is fair and only half or so of the main is out this won't present a problem unless someone is standing on one of the cockpit seats which people should not do. You can turn the boat through the wind with the wind from in front of the boat and the turn will be more tranquil. The main will flap a bit and settle down going the other way. Just make sure you are moving fast enough to complete the turn. Oh, did I mention that for this training session you can have the motor running but with the gear in neutral or in forward at idle. If you have a problem getting the bow past the "Eye of the wind" a little gentle forward with the motor will finish the turn.
This is my judgement of how to have your first sailing experience on a 40' boat - I expect you would have liked to learn sailing in another way.

Don S/V ILLusion · Feb 20, 2019

Most people in your situation hire a captain to help them learn. He/she can teach docking, undocking, picking up a mooring and obviously sail handling on your own boat which is always preferable to a generic sailing school lesson. Such people are very prevalent in the Miami area and you can get some good recommendations by asking/visiting any local marina office or yacht club.

TomY · Feb 20, 2019

Momof3k said:
I am so happy this is anonymous because this question is embarrassing. My husband bought a 40.5 Hunter sailboat(mid-life crisis??) . The problem is that he has never been sailing on his boat, or any other boat...ever.......
The boat came with everything and he knows the basics but again, has never sailed. We looked for someone local for lessons but they were just too expensive for us right now. Does anyone know of a website or any advice to get us sailing this weekend. Just for a couple of hours. His boat is moored off Key Biscayne.
The hubby is really smart and handy and since he has been living on the boat for hte last 6 months, he knows all the parts and what does what and what goes where but the actually sailing part is not happening. I am hoping to be able to give him some advice from all you experts and we can learn together. Can anyone offer any help or guidance...????

If you're serious, have your husband borrow a small boat first, to try to learn to sail. Leave the 40.5 tied up for living on.

Don't go with him until you're satisfied he can get you back to the dock. Seriously.

BlowMeAway · Feb 20, 2019

Hello @Momof3k, welcome to the SBO forum. Besides the fact that your request begs more questions then immediate answers, I simply interpret the text as looking for crew? Is that correct?

My conscience won’t allow me to make other recommendations for fear of misleading you on your first day sail on 40 foot sailboat, and then reading about another tragic grounding or sinking near Key Biscayne.

If your husband has been living aboard, on a mooring, I’m sure he must have met some other sailors at the Marina who would be willing to assist for nothing more then a few cocktails when you get back...maybe a dinner too!

Another online forum that has a “Crew Wanted” section is cruisersforum.com. They have a fairly large Floridian following and you may get lucky there.

Please don’t sail that boat without some experience on board. If you know how to leave a mooring and power your way around the bay (with the auxiliary) and get back...I’d think that would be a good start.

shemandr · Feb 20, 2019

Oh. And buy a membership in one of the towing companies. Tow USA or Sea Tow. They can make a mistake less expensive.

thinwater · Feb 20, 2019

I don't understand buying a big boat without learning to sail a dingy first. Would you buy a Winnebago without learning to cross streets and ride a bike first? A big boat only slows learning and probably prevents some lessons.

jon hansen · Feb 20, 2019

i taught my kids to drive in an 89' town car. that way they can drive everything. next they were put in a stick shift car.
it comes down to the student. all boats sail the same. the bigger boats tend to have more NON-sailing gear to learn. the sailing is all the same. 10' .....50' ....150' .... 250' all sail the same
trim the sails, hold on to the tiller. easy peasey

markwbird · Feb 20, 2019

He's living on the boat? My best advice is to sell the boat and take up sailing with a local club and see if he likes it. He can then decide if and what boat he wants to buy. A boat that big is very expensive to keep and maintain. Not worth it for someone with no sailing experience.

TomY · Feb 20, 2019

We sailed into Key Biscayne on the heels of Hurricane Hugo in the fall of 1989. Hugo had closed many bridges so we'd sailed off the coast of Florida and came in at night.

Tired, raining, I tried to stay in the channel leading in (can't recall where) but the current was fierce. Turns out the loran and my piloting on the chart were not up to the task.

Seems there were lights everywhere that made no sense (the lights turned out to be houses on stilts,...). I must have worn out a pencil plotting bearings as the depth sounder kept reading 14,13,12,11,,.....

Finally, totally lost and confused, our keel started thumping on the packed sand. Whump,,... whump,...whump,..

I threw my hands up and told my wife, "I have no idea where we are,..." as the boat fetched up on the bottom in the pitch black.

Truth is, we were relieved to be stopped. Invisible waves crashed on the hull as the boat took up on a sand bank. She was solid on the bottom now. It felt good.

I waded in shallow water into the wind with an anchor on the sand flats as far as the rode allowed, and dropped it.

We had a lovely dinner comfortably grounded. I remember a few beers that never tasted as good, again. As the boat laid over all the way, the three of us (we had a dear Springer Spaniel with us) slept like babies.

Dawn unveiled a beautiful morning. We we just floating and swinging on the anchor. We made our way past the curious houses on stilts in the water into the state park at Key Biscayne. 2000 miles, we were just starting to get it.

jon hansen · Feb 20, 2019

i can teach you to safely sail around the harbor or bay and docking in a day. no brainer. going out farther needs new skills. say stay inside of a twenty mile radius, easy to learn. then you keep adding to your skills from there.

jon hansen · Feb 20, 2019

so ........ first you learn some basics. practice those allot. then you slowly add more skills. the size of the training vessel does not matter.
start with the basics of sailing , add on from there

jmce1587 · Feb 20, 2019

+1 on Gunni’s recommendation for either ASA or Colgate basic keelboat school in the Miami area. They are not that expensive and he will learn a lot. From there he will meet licensed Captain/Instructors who conduct these classes and typically offer (for a reasonable hourly rate) individual lessons on your boat after the class.

Also +1 on joining TowBoat US or SeaTow on their top plans. Worth every penny and should something happen, it will be cheaper and less stressful to call on their services. I know from personal experience when I lost my rudder.