question for those who know how to sail
Sailing on smaller boats (14ft) is very different from sailing a larger (25 ft) boat. I learned in a 14 foot boat, and it was alot of fun. It is a much more active experience. Depending on how windy it is, you may have to hike out to keep the boat level. There is always the possibility of capsizing, although if you are taught properly this should not happen. You really feel the action or movement of the smaller boat. It can be alot of fun. Also, typically you can''t take many people out with you and still be comfortable.
A larger boat, I think, is more relaxing and less physically demanding. You are not having to hike out to keep the boat level. You will probably have winches to help with the lines. Depending on the boat you will typically feel less of the action or movement. You can take more people out with you, which is a big plus! You will typically have a motor which will make docking easier.
I had a 33 foot boat with a full keel last year and moved to a 26 foot which should be more fun to sail. There are so many choices out there. Figure out what you want to do with a sailboat, try some out, take some lessons, and make the plunge. Its alot of fun no matter what you get.