OP, as a fellow native Alabamian who learned to sail on Mobile Bay and have been sailing,
racing, and cruising for over 50 years, I’ll offer the following which reinforces some of what has been stated.
1. Go ahead and take the
ASA sailing course and then shop for a small 16-18 foot daysailor (buy new so it works, check out RS Sailboats) and take at least 1 year to sail that boat as much as possible and really learn to sail. Small boats are WAY better than big boats for
learning as they are easier to sail and much more responsive and you are focusing on
learning to sail and not distracted by building or fixing a boat. If you invest in some cold
weather sailing
gear, you can sail on most all days on the
Gulf coast.
2. Treat sailing like learning to fly because both
water and altitude can kill you. When you start, limit yourself to sailing only days where the
wind is 10-12 knots or LESS. If you go out on a windy day with little to no experience, you will scare the crap out of yourself and your wife. Become proficient in light to moderate air and then venture into sailing in bigger
wind. Better yet, find an experienced sailor that can go with you or take you out on their boat in bigger breeze (I’m talking 12-18 knots) to get you comfortable with the conditions.
3. If you progress above, after a year consider going on an
offshore sailing
training cruise. There are several companies that offer these type of trips on 40-50 foot boats. The crew size is typically limited to 5-6 sailors and everyone is part of the crew so you will cook, clean, trim
sails,
helm, be on watch, etc. It will be REAL WORLD
training that will be invaluable.
4. At that point, you are probably ready to consider
buying (as recommended) a new or very well maintained 30’-35’
cruising sailboat. If you make the move to the
Gulf coast, it would be an excellent training ground for coastal cruising where you can sail from P’Cola to Destin or
Panama City. You can then graduate to a longer
passage like P’Cola to St. Pete. You can even coastal hop to the Keys or a
destination like the
Dry Tortugas as you build experience. The point is start small with 2-3 day trips and figure out what works and what does not
work.
5. All of the above should translate to at least 3-4 years of building a foundation and learning what will work for you. At that point, maybe you will have enough experience and knowledge to buy a bigger
live aboard and consider going
offshore. I would even consider still limiting yourself to coastal and do a couple more offshore sailing training trips as suggested in (3) above before you venture into the open ocean for long distance
passage sailing.
I wish you the best of luck with your dream. Have fun but be smart and safe.