If you are just beginning, or moving from dinghy to keel boat, I suggest taking the first three ASA courses (
American Sailing Association - Learning to sail is just the beginning...) at a location with comfortable weather. ASA is the three-star "Holiday Inn" sailing school - basic standards and safe. Some are excellent, but at all of them you will get basic instruction with a common set of books. The advantage is that their certificates are recognized by charter companies (first three courses usually required to bare-boat charter). In your goals, you probably will want to charter for a week once or twice as it will help you decide what boat style you like, and even if you (and your partner) really like that sort of life. Personally, I would not trust my boat to someone who has just had 8 days of instruction and little practice, but I do not carry the insurance that charter companies carry! BTW: for a specific school in warmer weather, Offshore Sailing/Colgate (West coast Florida and BVI) and the Blue Water sailing school (Ft. Lauderdale and BVI) are both recommended.
The first ASA course (101) is almost all vocabulary and a little on-water time teaching you about wind, sail trim, and basic sailing. If you already can sail and name most of the things on your H23, you may not need the instruction, so you may be able to test out of the course for about $100 (30 question multi-choice, plus some point-and-name drill aboard a boat about your sized), and get the certificate before the 103 course. The next two courses are managing a keel boat with all the installed systems. The courses are really packed in the day, and if you have not read the book before arriving, reading the lessons at night, so not much of a vacation. You can buy the ASA books on Amazon, if you want to read ahead. I always advise people not to take the all-in-one courses 101-103-104 in a week because you just cannot absorb that much info, but to each his own and some people want it all done in a week. The 105 navigation course (at home reading course with a proctored test at most ASA places) is actually really useful as it teaches you ded-reckoning navigation so you can get home.
