I loved every sailboat that I ever owned or sailed. From the 9' SportYak with its plastic lateen sail and oar for a rudder, to the 54' Irwin ketch and all of the Lasers, windsurfers, centerboarders, and Hobies in between. It's where you are (lake, ocean), not the boat that is important. It's the journey not the destination.

With that little bit of Zen behind us let's tackle the problem. The boat that you can sail the most often is the best boat for you. If you can car top a windsurfer or Laser to work with you and then sail in the evening then that may me the right size boat for you. I used to drag my Laser down the beach almost every evening and watch the sun go down from offshore. Would it have been more fun if I were on a beach cat? Maybe, but being on the ocean every night was and is priceless regardless of the boat you are on.

If the need for speed is what sets you free then consider a motorcycle and a Laser or a big beach cat like the Hobie20. I single hand mine all the time, its easy. Catamarans are incredibly stable. Sometimes I carry 8 or 9 people on board and sometimes I tow a tube with a couple of kids behind. Its all fun. One fact of life about all beach cats is that they are all very wet boats. Which is fine as long as you and your guests are prepared, but if your girlfriend doesn't really like to get her hair wet then you might want to get a stable center boarder like a Flying Scott. If you are day sailing with girls onboard then you had better be ready for bathroom breaks if you ever want them to sail with you again. That may require a boat with a small cabin. There are lots to choose from. Like I said, its more about where you are (on the water) than what you are there on. If you are just trying to please yourself then keep in mind that often simpler is better. Sometimes I prefer my windsurfer to the Hobie 20 because it is simpler and easier and it gets me on the water quicker.

One thing for sure is that you will always be on the lookout for the right boat. It never ends.

Best of luck