
As Zane mentioned, learning to sail is a primary step in our plan. After all, it wouldn't be very smart to sell everything and buy a sailboat without knowing how to use it. There are many ways to learn to sail including just getting a boat and winging it. To make sure that we set off with as much knowledge and experience as we can get, we are both going to go to sailing school. There are also several options for sailing school, for example: Which certification organization? Which school? Go local or travel?
There are two major sailing instruction organizations in the US, the American Sailing Association (ASA) and the United States Sailing Association. Both organizations provide a full range of instruction and certification from Basic Keelboat sailing to Offshore Passage Making. Neither certification is considered "better" than the other, although the US Sailing certification is sometimes favored among racing crews. Since Zane and I only plan to race dolphins, and I already have experience with ASA, we'll be pursing ASA certification. The ASA website has a directory of schools throughout the US and the world, and there are four schools in our area to choose from.
When choosing a school, it's good to visit them so you can get a feel for the boats they use as well as the personalities of the instructors. It's also good to talk to previous students if you can. I had taken the out of the water, or 'ground school', portion of the Basic Keelboat sailing course several years ago with my father, so I am already familiar with Windsong Sailing Academy. I've also done a few of their 2-hour on-the-water sessions, and the people there are great. If you can't find a school in your area that you feel comfortable with, there are also several schools that offer vacation style courses.
Blue Water Sailing School and Offshore Sailing School both offer options for vacation style courses. With Blue Water Sailing School, you can take multi-day live-aboard courses and obtain instruction and certification while on the boat. Offshore Sailing School offers week long course at some resort locations that includes morning classrom sessions and half-days of on-water instruction leaving plenty of time for other activities at the resort. A quick Google search can find you several other similar options.
Whether you choose ASA or US Sailing and take courses at a local school, or take a vacation to learn to sail, sailing schools provide many great opportunities to learn to sail. For us, they are a way to ensure that we learn the skills required to safely cruise the world's oceans. If you don't already know how to sail, take a course and maybe we'll see you on the water someday.

