The size of a sailboat can play a significant part in its capabilities. Generally, if you want a cabin with living space, you’ll need to go above 20-feet. For standing headroom, you’ll want to search for a yacht 25-feet and up. If you plan on taking extended blue water voyages, you’ll need to be careful when choosing a sailboat size. With too big a boat, it’ll be very difficult to handle yourself. Too small and it’ll be uncomfortable. For single-handed offshore passages, boats between 26 and 35-feet are often appropriate.
Other factors to consider are; marina fees – you will pay more for storage of larger boats, and haul outs – regular boat maintenance is an ongoing cost for boat owners and, like marina fees, the larger the vessel the more expensive it is to haul out and keep maintained.