my biggest fear would be to safely maintain control of the boat in the event of a big storm.
Would bad weather be a problem during late December early January?
I'm not familier with the area you are planning on sailing in but last summer my son about 22 years old very fit and a 10 year experienced sailor and current marine mechanic decided to sail with my friend and me from Connecticut to Long Island. We were in a 27' sailboat he took the Hobie 16'.
The wind picked up and we found out a few things about the Hobie 16.
1. With wind about 30knots+ and waves about 6 feet which was just perfect for the 27 Catalina the Hobie would not go to windward. So you may not be able to sail in the direction you want to go.
2. He is about 140lbs and just staying on the boat was a major effort. Actually sailing was practially impossible.
3. He lost a boat hook. Keeping things on deck is not as easy as it seems.
4. He ripped a jib track off the hull. The hobie is not built to handle that kind of strain.
If the wind picks up even a little your need full attention to keep the boat upright. Your weight, in the right place second by second is the trick. One misjudgement by one second and the boat is overturned and you are in the water. Righting the Hobie in calm conditions is fun. In rough conditions probably not possible.
Don't forget that even if you drop your sails you have a trampoline that will act like a sail but its only goal will be to flip you.
In short in good conditions anything that floats will get you to where you want to go.
So you have to weigh the risk. The intent of the Hobie is to have fun on the water. It has practically no ability to protect you from the elements. Dumping a Hobie or falling off it is part of it's fun. If you can swim to where you want to go the Hobie will increase the fun. If you dump or fall off and you cann't swim to land or be picked up by another boat you will be in the water untill someone finds you.