If you're contemplating making the transition from landlubber to someone who can leave and return to the dock under sail in a seaman-like fashion, it may be helpful to remember that all sailors started on land. Despite the grace with which some sailors maneuver their vessels, no one is born with a set of skills that comprise good boat handling and there is no substitute for hard-won experience. The question is how to get out on the water and glean the insight that will make you a better sailor.
If you insist on making a solo run your first time on board, use common sense and be prudent. Reading up on the basics beforehand can take some of the mystery out of what is happening. Understanding the theory behind how the boat is moving will make learning on the water easier and safer. Of course you should wear a lifejacket, and I recommend that you don't try this on an overly windy day. Also, a small body of water with light traffic is a better choice than a large body of water with plenty of boats. Be cautious and at least recognize the fact that you don't entirely know what you are doing. Finally, have someone standing by in case you'll need rescuing.
Becoming a Crew
Befriending a boat owner through dockside PR
skills can get you out on the water quickly and is usually a safer way to go. Many marinas and yacht clubs have bulletin boards where a variety of boat related communication takes place. Posting a small sign stating that you are looking to crew on a boat or are willing to work in exchange for sailing experience is a good place to start. In the beginning, enthusiasm is an important part of getting out on the water.
While asking someone you don't know for a ride may seem intimidating at first, most sailors are more than happy to spread their knowledge and it beats standing on the dock watching everyone pull away. However, if your potential ride seems gruff or starts using power tools in mid-sentence, move along.
Sailing School Nearly every coastal city has a sailing school with boats, instructors, and the know-how to convert a beginning student into a skipper. Sailing schools can fall anywhere in a wide spectrum ranging from funky mom-and-pop organizations to nationally accredited businesses with would-be Olympians doing the instructing. Call around and get an idea of how involved the program is, the length of instruction, the types of boats, and what kinds of certification, if any, the school offers. Do they teach just basics or do they offer extended cruising classes. Class size and schedule flexibility are other important factors. At the conclusion of the program to what will you be entitled? Will the lack of a certification hinder you elsewhere? Do they have any free introductory lessons to see if sailing is for you?
There may be local clubs, volunteer organizations, or informal groups that can impart the skills you need. The US Coast Guard Auxiliary and the US Power Squadron teach courses covering topics ranging from basic navigation to diesel engine maintenance.
Another option you have for learning how to sail is to integrate your instruction with a vacation. If you want to bypass the fundamentals and go right to sailing in a tropical paradise, there are captains and crews waiting for you throughout the Caribbean, Mediterranean, and the South Pacific. Some charters are instruction-oriented, while others emphasize a more hedonistic existence, eating, sleeping, and lounging in the sun. The advantage of these is that you set the pace, learning as much or as little as you want to. The downside is, depending upon the season and the location, this can be one of the most expensive ways of gaining proficiency as a sailor
Keep in mind that no matter which way you chose to get out on the water, flubbed dockings and other nautical snafus are likely to befall you from time to time. Experience is the ultimate instructor, so even though you may not get everything right at first, large doses of practice and patience will ensure that sunny, breezy days in the future will be spent the way they are supposed to be: ascending sailing's learning curve.
Learn to Sail in a Dinghy by Sue and Larry
Wind Orientation by Mark Matthews
Turning Passengers into Crew by Bruce Caldwell
Buying Guide: Personal Flotation Devices