Having lived on a 25 foot folkboat when I was in my early 20's, I have concluded that, while it is possible to live on a small boat, it becomes much more difficult to maintain a something resembling a 'normal' life in smaller boats; as in not showing up at work or a date looking like a homeless person.
With all due respect to SailingDog, I disaree with much of what Sailingdog has proposed. Having lived on and sailed the Chesapeake for the past 23 years, the Chesapeake is a wonderful cruising ground that very much rewards boats that are good boats in lighter winds and boats with enough speed to have a reasonable range in a day. For that reason I suggest that he focus on sellecting a displacement range that is adequate to support a liveaboard lifestyle, and then look for boats that are on the long side for that displacement. I would suggest a displacement of minimally around 8400 lbs, with a displacement in the 10,000 to 11,000 lb. range. I would then suggest that that should translate to a 32 to 36 length.
To a great extent boat prices are set more by displacement and age rather than length. While it is true that some costs are related to the length of the boat, most of the costs listed in SailingDogs post (cost of the equipment, such as sails, running rigging, standing rigging, winches) are much more related to the displacement of the boat than its length, and if your son does most of his own maintenance, a lot of costs such as the cost of bottom painting, is more related to displacement than length.
Similarly, more and more marinas are renting slips by the slip length rather than boat length. But beyond that he would save a lot of money of he can find a private slip and private slips are almost always rented by the slip length rather than the boat length. (For example I typically rent my 35 foot slips for $100 per month, a more with liveaboard electricity whether the boat is 25 feet or 35 feet) In other words a few feet of length one way or another should not add significantly to his costs, but it will make his life aboard a lot more comfortable and his sailing experiences on the Bay a lot more enjoyable.
One last point, most double enders tend to be at the heavier end of the weight to length spectrum which would mean a whole lot more motoring to sailing here on the Bay. Also they typically offer significantly less usable space for their length than a transom boat.
I am suggesting the boats on the list of suggestions below with the intention that that each represents a reasonable balance between accomodations, build quality, cost and sailing ability, with individual boats biased one way or another.:
Beneteau First 305: These boats have a great layout down below and seem to have held up very well.
Bristol 34 (1970's): Good sailing comfortable boats all around.
Cal 34 (1960's through 1980's): These boats are everywhere. They sail well, have reasonably good construction and would be near the top of my list for what your son wants to do. You can find them for sale between $12,000 and $25,000 with the older better maintained ones selling for $15K or so.
Hunter 34 (early 1980's) I know that everyone pans Hunters but the 34 was a very nice sailing boat with good accommodations, a lot of nice features, and Hunters of that era were quite reasonably well built.
J-30: Probably not the best choice on this list in terms of accomodations, but these boats are quite common on the Chesapeake and offer the most fun sailing of any of the boats on this list.
Irwin Citation 34: This is at the more expensive end of the price range. My sense of these boats is that they are not as well as the Hunters, but you sometimes see these at a bargain price due to cosmetics and since they are generally more highly regarded than Hunters in the court of 'general wisdom', I would suggest in someways a fixer upper may be a better investment.
Pearson 323: These were designed as cruising boats and make a very good choice is light air sailing is a lower priority.
Pearson 30: Cheap and common as dirt on the Chesapeake. Good all around boats. Not terribly roomy but because many of them were raced one-design, you can often find them well maintained and upgraded at a bargain basement price.
Pearson 10M: While there are some design and construction details on these boats that drive me crazy, they can often be bought cheaply and are very nice boats all around.
Tartan 30: These are one of my favorite boats of this size, era and cost. They are quite common on the Chesapeake. I just recently looked at one that was in super condition, both in terms of maintenance and upgrades, that was priced extremely cheaply. I walked away thinking what a great boat.
Tartan 34 (1970's): Excellent all around Bay boats. I have aways loved these boats. You can find them priced all over the board, with lovingly restored versions selling for close to $30K but less pristine versions selling for a lot less. One downside, partially offset by the large cockpit, is that these boats do not have much room for a 34 footer.
Last edited by Jeff_H; 08-05-2006 at 10:24 AM.