As for choosing a boat to sail with, I suggest trying a couple of different boats at the beginning. Each boat has its own particular style and attributes. When you find one that is comfortable for you, patronize that boat as a regular. Remember that it is a business in which regular customers are valued highly. Crews are more willing to go the extra distance for a regular customer. While on the subject of crews, their regular salary is nothing to brag about. They depend upon tips to make a descent day's pay. Winter weather is an important consideration in planning a trip. During this time of year, windless, warm and dry days are almost unheard of, and a certain amount of discomfort is to be expected. However, to board a boat when the forecast calls for winds in excess of 20 mph., temperatures below 20 degrees, and a possibility of sleet or snow is asking for trouble. For these reasons, I avoid long range plans. I listen to the forecasts and wait for the right day, usually finalizing my plan the night before. Concerning proper dress, the rule is light but warm. Layers of lighter weight clothing provide warmth without restricting movement. A quality set of lightweight thermal underwear, such as made by Helly Hansen, warm street clothes and a set of coveralls containing thinsulate is usually sufficient for basic warmth. Insulated waterproof boots and gloves are a must, as is a heavy duty set of foul weather gear for when conditions get sloppy or for added warmth. Don't forget that a great amount of body heat is lost from an uncovered head, so a quality woolen watchcap that can be pulled down over the ears is also in order. In addition, winter seas are usually lumpy even on windless days, so take the normal precautions to prevent seasickness.