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A very pretty Bermuda 40 yawl all tricked out for voyaging. This picture was taken during a training cruise. The students got a chance to look at the B-40's details and discuss the features. A lot of learning happens when you go on a training cruise, even if it is just a few days in duration.
The cost of cruising is the same as the cost of doing anything else, it can be as expensive or cheap as you like. Mostly, the way you live ashore is the way you will live aboard so those costs are going to translate pretty well from house to boat.
There is no perfect boat. The proof is that when you are out there, you'll see a lot of different boats each with a happy cruiser aboard. What about the unhappy cruisers? They quit and it isn't the boat that does it.
Cruising yachts rafted to pontoons in Camden Maine, Inner Harbor. Each on a "perfect boat."
- American Sailing Association's Advanced Coastal Cruising http://asa.com/certifications/
- United States Sailing Association's Coastal Passagemaking http://www.ussailing.org/
Maybe charter a few times in a couple of different places on a few different types of yachts. The instructors, charter captains, and other professionals will provide barrels of useful information. Sailing with a professional will help the student acquire a library of best practices.
One dinghy has its oars stowed improperly!
Continuing education? Consider the USCG Captain's license sometimes called the "six-pack." Even if you do not have the time required for the full license, the course of study and tests will boost your capabilities greatly. Racing is a practical way to get in some sailing time and improve one's skills. Two types of races that are really good for cruisers are pursuit races and double handed races. They don't feature the crazy maneuvering tactics of small boat fleets. In fact, most of the participants are cruisers trying to improve their boats and the owner/couple's skills.
A Gulf 32 with a new suit of sails finishing well up in the fleet during a large pursuit style race. Good sails and a clean bottom made a big improvement in the performance of the yacht.