Hi, and welcome to Hobie sailing and sailign in general!)
While a hobie 16 does not go to windward as well as an Americas Cup Yacht, or even a well sailed dinghy, I would not say a 16 cannot go to windward.
As a sailing coach for a number of years in my teens, I can say that most new sailors think they are going to windward when they are really close reaching. The trick is to sail as close to the wind as you can without DRAMATICALLY losing speed. It is an art form, more than a science, but it is easily learned. It is best learned by going sailing, (ideally on a 16, but any sailboat will give you the idea) with an accomplished sailor to show what things should look and feel like.
If you cannot get an accomplished Hobie sailoer to go out with you, or let you ride on their boat, I recommend taking sailing lessons- if thats not an option, try sailing instructional videos. Point is, you really need some visuals to be able to figure out how to do this. Words don't help that much in the very beginning.
Having said that, as a starting point, to go to windward in mderate air- main and job travellers all the way to the center line. Main sheet pulled in until boom is almost over the centerline. The leach (back edge) of the sail is your "rough tuning " guide. When you get most of the twist out of it, your'e getting close.
Jib, pulled in tight. Then, learn to read the tell tales on your sail to keep air flowing over both sides of the mainsail, and continuously keep trying to head up a LITTLE bit more, see what the tell tales do, to keep going to windward as best you can. Racers will cringe at some of the above- these are rough settings that will get you going, not finetuning advice.
It may take years to be able to go to windward like a national champ, but you should be able to get 90-95% of the way there after a few days on the water with an experienced teacher.
Hope that helps a little.
_________________ Raced extensively as a kid (against Matt Bounds!!), just bought a 20 year old 16 and am refurbishing it.
Sail # 21888
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