What about school for Graham?
Graham is 12 and he is starting middle school in the 6th grade. We have enrolled Graham in the Calvert School (http://www.calvertschool.org/) which is a well known home schooling program that is often used by cruisers. Part of the reason for starting now is because we feel like we are able to home school Graham successfully in grades 6-8. High School home schooling is a lot harder, so we plan to return to the real world for his high school years.
I’m interested in sailing and learning more about the cruising life. What could I do to get started or to brush up on my sailing skills?
If I was starting back into sailing I would probably do a couple of things right away. I think I would join the Sailing Club of Washington http://scow.org/. SCOW is a good organization for getting reconnected. It is easy to get over there after work for their social activities and sailing. Getting their Skipper designation allows you unlimited access to their Flying Scots which are decent daysailors. The sailing class is probably full up by now but you can pass the test without taking the class. I might have someone you could contact if you want to some help with the test. Get on their listserve, lots of people look for crew to sail with on nice days. There are quite a few Chesapeake Bay sailors in the club and they often take crew with them. Decent social scene. One of my friends met his wife at a SCOW social function. Next, I would join the Seven Seas Cruising Association http://ssca.org/cgi-bin/pagegen.pl?pg=home&title=Home. SSCA has quite a few great resources for cruising sailors. I would try to make time to go to one of their GAMS. There is always one in Annapolis around the same time of the boat show. The cost of joining SCOW and SSCA should be less than $100. Add $150 to that for a SCOW Skipper.
You might also consider racing. Racing is a really great way to bring your skills up to snuff in a big hurry. Racing sailors are really good about teaching their crew the finer points. The thing about racing is it is not very relaxing. Some people are turned off by the intensity. There are lots of crew lists for racing sailors on the internet. If you are going to race you need to get decent foul weather gear. If you have lots of fleece and outdoor type gear from another outdoor sport, that should be good to get started. Layers are the way to go. Foul weather pants are just as important as a good jacket. I invested in some good Musto GoreTex . A good set of sailing shoes are a must-don’t go barefoot. Cost of gear for racing: $200-500
Another option that costs more but might also get`you into the cruising mode faster is to take courses from American Sailing Association ASA schools. I’m partial to the folks at JWorld Annapolis: http://www.jworldannapolis.com. Although they are not ASA. ASA classes are accepted by charter companies. A basic bareboat certification and a navigation class would qualify you to charter boats on the Bay or here in the Caribbean. Some of the sailing magazines offer organized sailing weeks in some great cruising locales. I have never tried that, but they look like fun.
At the very high end are training programs on passagemaking. John and Amanda Neale offer an introductory weekend seminar for about $400. Their on boat passagemaking course is supposed to be terrific. There is information about these programs on their website, which also has some good concise information about what is takes to go cruising. Their web site is: http://www.mahina.com/ Amy and I also took a weekend preparation course from the World Cruising Club. This is oriented to boat owners.
One other thing that is coming up soon: The Safety at Sea seminar put on by MTAM, West Marine, and the Naval Academy is probably the best $$$ I ever spent. It was a real eye opener and had some great demonstrations. I would attend again if I could and take the whole family. You can sign up here: http://mtam.org/safety-at-sea.html The 2012 seminar is March 31st.
One other thing I would consider after I got started with some of the other programs here is taking some weather courses. We use a weather service, Chris Parker at http://mwxc.com/, which is invaluable. I would watch for one of his courses being taught in your area and attend that.