The first boats I heard about being used for paddling and sailing were canoes. John MacGregor paddled his Rob Roy canoes around Europe in the 1800's and ever since then paddling and sailing has gotten more popular. In those early days the canoe and the decked canoe were the only choices. Even then boats had to be individually built by highly trained craftsmen and they were usually expensive custom made tools for the wealthy.
Now boats are available across a wide spectrum of styles, materials, and manufacturing techniques. You can still buy the custom crafted wood canoe or sailing craft for between $4000 and $32000 for a canoe. And you can find a durable plastic kayak for less than $300. Now any family can afford a paddling and sailing craft.
I used canoes at first because of the waters I visited were usually calm. In rougher waters I had to tie in float bags and carry a pump and bailing bucket. With the canoe I could only reasonably sail in warmer waters because capsize recovery was a long drawn out affair that meant a lot of time spent in cold water. Even with a wet suit or dry suit I would be soaking in sweat if I dressed for the water rescue and too cold if i dressed for the air. I know dry suits are supposed to be breathable to eliminate moisture buildup. However, the life vest blocks a lot of this moisture from leaving the dry suit.
Later I tried kayaks for paddling and sailing and found the sit on top to be an ideal solution for my sailing conditions. You sit in the water in a sit on top so if you dress for the water you will be just fine. If you get a little warm you can just put your legs in the water and splash yourself to cool down. If you have dry gear you can stay dry as well. Sit on top recoveries are much easier to learn that kayak rolling or deep water canoe rescue and usually much faster. In addition it is easy to add stability to a sit on top by putting your legs in the water. This helps a lot when raising or lowering the mast or sail and when tending the rigging in other ways.
I had been paddling for about 40 years before I had a sit on top. I wish I had gotten one much sooner. Unfortunately most of the sit on tops you see today are better fishing and diving craft than travelling craft. They are wide and heavy. They paddle like a plastic barge. But there are a few companies that make acceptable craft that are very comfortable and good for 20 mile days. In fact whenever I want to paddle more than 20 miles for more than one day in a row I will choose the comfortable sit on top.
My favorite sit on top site is:
They sell some great sailing rigs and paddling gear!