Hey Uki,
Good to hear from you. I was just thinking about you. Last we heard you were going to modify your cabin and go sail the Apostles. I figured the weather in Wisconsin was pretty brisk this time of year and you'd be coming ashore some time soon. (I spent my first 22 years in Michigan, so I'm familiar with the weather.)
As for what can be done in a DS. Well, what
can be done and what can
comfortably be done is a whole 'nother thing. If someone is 18-25 years old, a strong swimmer, has a lot of experience, survival gear, jacklines & harness, and a rescue crew on hand I bet you could take a DS around the world.
On the other hand, things that the
boat is strong enough to take may overwhelm the
captain & crew. A reasonably fit person can sail in some real rough waves and strong wind for a few hours but staying braced is fatiguing. After a few hours your arms and legs will cramp up. Being able to get food and drink will be difficult at best. Dehydration will accelerate fatigue.
As the hammering and bouncing continues and the hours turn to days and you have had no sleep your judgement will fail. You will see things that are not there, you will not see things that are there. Dangerous.
The infamous "great lakes chop" can hammer a boat to pieces. (For a given wave height, the ocean is smoother than the great lakes.) On the big lakes the weather changes quickly, and by location. I've spent time on Lake Erie where in
one afternoon I was becalmed, blown over, was snowed on, and wore shorts. Am I on "hidden camera"?
This is unreal...
Ah, Florida. My current home. The winter sailing is nice. Just watch the weather in the summer / fall. The afternoon squalls come up mighty fast in the FL keys & in the Gulf. As another poster mentioned, being able to close up the cabin would be a big advantage. When you see one, you barely have time to secure all hatches and don a PFD before it hits.
I'd recommend going no further off shore than you can return from in an hour or two. If bad weather comes, you can duck for cover. For anything further than that offshore I would recommend a much bigger boat ... 23-26 feet minimum, (30-35 feet good), a fixed keel (you can move about while underway and not worry about rolling over and the added mass really smoothes the ride), big enough for proper padded bunks, at least some electrical (nav & anchor lights & 2 way radio & autopilot & electric bilge pump), a bimini top (sun and rain protection reduces fatigue).
The real difference between ordeal and adventure is attitude. But a hot meal, a cold drink, and a soft bunk can help attitude a whole lot.