s/v Adeline, this must be really frustrating, here you want routing
advice, and a lot of people with experience are questioning your readiness and that of your
boat.
I'm clear across the world from you in
Australia, and I am going to try and explain why this is happening. In
winter, in the northern hemisphere, the northerly quadrant winds you want to head south on will be coming with the passing cold fronts (storms) that sweep down from
Alaska and across the US. The Gulf Stream consists of warmer
water, northbound, to warm the south coast of
England, and beyond. When the north
wind encounters the northbound
water, the waves peak up, becoming steeper and of course wave height increases with wind strength. Such sea states can get really ugly, scary, and vastly fatiguing to sail in. This is why it would be challenging, if you were an experienced
skipper and knew your
boat was sound. Such a
skipper would expect
equipment failures (because such sailing is hard on the boat.) All that before you get around FL. and head for AL.
The issue of the soundness of your boat was first addressed by Dockhead, who suggested a shakedown period. Given your constraints of distance, time, and
money, I hope you can manage some sort of a shakedown. Your boat hasn't been shook enough yet. It is not necessarily over yet, the fixit stage, I mean.
Others have suggested a trip down the ICW as far as you get. You're in a very awkward position here with needing to have the boat where you live in order to fix her up and it being so far away to your home.
If it must be done, the only way I can see for you to do it would be to plan on sailing, not stopping anywhere. You must replace your halyards first, don't want one breaking on you, under sail. Carefully examine the
sails. If there is chafed thread on the seams, buy a sailors palm, and some sewing twine, and stitch those seams by hand, that's the cheapest, but the most labor intensive. Otherwise, if there are funds, take the
sails (the
genoa, the working
jib, and the main sail) to the
sailmaker and ask if they can be re-stitched. The
sailmaker will tell you if the cloth is finished its life. (Or, if you can stick a sharpened #2 pencil through it, you can tell for yourself. Sailcloth can get so used that it's that rotten. Don't go this year, if you have to have new sails made.
If you think you have enough sailing experience to be responsible for a crew, take two other people, the more experienced sailors, the better. [If you don't, yet, then abort the mission. We all want you guys healthy and happy.] Most
women would not enjoy what you are about to do [nobody likes being cold, tired, and terrified] , so let your good lady wife help by preparing
meals ahead that you can just heat up. Bring her only if she insists on being there to help, and if she's a proven watch stander. Bring medicine against seasickness that you know works, and something extra (like suppositories) to control vomiting if the meds don't
work. Understand that if any crew is seasick, you're going to have to abort and get them to land, you have a "duty of care" for them.
Accept that you may lose your job over this, because boats sometimes cannot make much progress in bad weather, and you could still be at sea when your time is up. I'm sorry to say, I really can't guarantee that if you left when you say and went straight through you can make it in time. It's a long way to go when you don't really know what to expect in the way of average days' runs, and all the human errors possible. It is partly about selecting departure weather, and having some
navigation and piloting skills. I've met some beginning sailors who were thrilled to have done their first overnight sail, what you're going to have to do is do it like a
delivery, and it will NOT be fun, it will be the nightmare part of the dream. Leave in gentle weather, to help your bodies get used to being at sea.
Good luck with it, man.
Ann