I bought a 25ft boat. Wish I got a 17ft trailer sailer! I know I will want a bigger boat, but I seriously recommend going a small as possible, dinghy or dayboat, then a small trailer boat, then when you are sure you are going to cross oceans go bigger. Joshua Slocums Spray was only 36'9. Robin Knox-Johnsons Suhaily is only 32 foot! Both went round the world single handed, the second one non-stop and before freeze-dried food!