Regarding the ease-of-use factor, I strongly agree that larger boats are NOT more difficult than smaller boats. I have sailed boats from 23 to 39 feet out of Boston habah
for the past three years. I have found that the larger boats are much more comfortable, especially when the wind kicks up and you start seeing 6' swells (common). If you are planning to sail with company, you will appreciate the extra room.
If you are not planning on staying in the Boston area, I would suggest joining one of the SEVEN
sailing clubs in Boston harbor. Both the BHSC
offer memberships in cruising boats. All you pay for is the use of the boat, the club pays for the rest (taxes, insurance, maintenance, mooring, fuel, ... everything!
). The other great aspect of the clubs is that you are able to try several different boats at your level of membership.
If you are looking to take the boat overnight, the cruising memberships allow that as well. Memberships at the two clubs I mention above (this year) range in cost from $2400 to $5800, and there are boat show specials for the next two days that will trim about 10% off that...