At just over a thousand dollars, the Snark is the cheapest sailboat you are likely to find. At 11 feet in length and just 50 pounds, the Super Snark sailboat can be easily transported to the water on top of your car, saving you the cost of a trailer or slip. The reason this boat is less expensive than most models is that it is constructed from plastic over foam core, whereas most sailboats are fiberglass. It is great model for children and adult beginners alike.
Walker Bay 8 and 10
These Walker Bay models provide all the basic functions of a dinghy in two lengths, 8 and 10 feet: row, motor, fish, and sail. Both of these models provide a Wheel in the Keel, which allows for the easiest of transportation in and out of the water. A great size and price make it ideal for the solo individual just starting out in the world of sailing. Remember that all the basic maneuvering of sailing can be learned on a small boat, with the knowledge transferred to a largest boat when the time is right.
Pico from Laser Performance is one the best bargains you will find in the bigger small boat category. There is room for a couple of adults or several children, and the handling is so easy that most amateurs can get in the sailing groove within the first few hours. The Pico has a removable jig and reefing main sail for easy rigging and transport. Two sails promote teamwork for a child and parent sailing lesson, or the Pico can be sailed solo.
The Sunfish, also from Laser Performance, is perhaps the most tried and true sailboat option. It's been around for sixty years, and generations have sailed the waters on a versatile Sunfish. It features two easy rig lines, easy-snap sail rings, and a patented kick-up rudder for easy beaching. The self-proclaimed most popular recreational sailboat in history! Easy enough for the beginner and awesome enough for the most experienced sailor.
Hobie offers several sailboats that are great for the beginner. At the less expensive end of the spectrum, you may want to check out Hobie Island or Hobie Bravo. Hobie Island is a trimaran that will give you a foot-pedaling workout. Hobie Bravo may be better suited to children or the novice. Both catamaran styles are sure to help you acquire the knack of sailing, as well as get you wet in a super fun sailing experience. Good times for one or two people.