Howdy! Welcome Aboard this forum!
You mentioned you want to take some classes
in the future to prepare yourself for chartering and to gain skills.
My Suggestion: I highly recommend taking classes (if one can afford them) and the place I like to recommend is the San Francisco Bay Area.
My suggestion comes after years spent sailing on lakes (even in Texas) and then years sailing on San Francisco
Bay, around the Hawaiian Islands and in the Pacific too.
Why San Francisco Bay rather than a typical inland lake?
Typical lake sailing on small to medium sized lakes (not the Great Lakes) is usually relatively easy sailing with light to moderate winds (5- 10 knots) and usually benign sailing conditions (e.g. no tides, no currents, no big waves). Lake sailing like that can be good for beginners and pleasant for day sailing
. But it does not offer the same challenges and learning
experiences as other locations.
The San Francisco Bay offers many sailing challenges (e.g. typical daily winds in the summer months are 20-30 knots, chance to reef a main for real, tidal changes, strong currents, fog
, ship traffic, hundreds of sailboats sailing around for practicing right of way, etc.). All of that will provide experience that prepares one for "blue water" sailing without going "off shore."
It is a good confidence builder
, in that when one is taught to handle a boat in dependable (happens almost every day) steady 20+ knot
winds, it is not as intimidating later when stronger winds or squalls are encountered.
As I see it, beginners fear strong winds because they have only associated them with storms and they have only sailed in light winds (5-10 knots) on lakes or light wind
areas. Overcoming that fear, by practicing seamanship skills in 20 knots with a good instructor aboard is a great way to increase your skills and confidence.
Of course San Francisco is also a great place to visit when not on the water. Much to see and good food
too. And there is a lot of value in sailing around San Francisco as seeing the city or the Golden Gate Bridge from the deck
of a sailboat is something special and even "awesome" if one goes under the Golden Gate Bridge on a small boat. It is a great place to sail with challenges and beauty and much to see in the location after the day's sail.
Of course if one has the desire to charter
in the Caribbean, I would suggest, if they have the money
, to also take their classes in the islands where they hope to sail/charter. The advantage with this approach is that you are in warm water and learning something of your eventual cruising grounds (or waters) and you can enjoy a swim after sailing
. Unfortunately, the water in San Francisco is typically about 54 degrees (f) in the summer (so feels very cold) and so there is no snorkeling or swimming after a sail, but that is offset by all the many things one can do in San Francisco when off the boat.
You asked about going down to Galveston to sail there. While that may be better than Lake Lewisville (and I like that lake), I think you would more enjoy and learn more in San Francisco Bay. It is a "world class" sailing location.
Where would I go?
If I were going to spend lots of money
on school fees
plus transportation etc, I would choose to do it in a location that offers more than just time on the water, but most importantly look for the place where I am challenged the most.
There are several sailing schools in San Francisco, but the one I enjoyed is Club Nautique. They have many boats in their fleet, lots of experienced and qualified instructors, and very good locations (Sausalito and Alameda). http://www.clubnautique.net
Good luck on your sailing adventures and have fun!