About 7000 miles around the coast, Texas to the Keys, the Bahamas, and on up to the Chesapeake and then return to Texas, around the coast. A third of that single handed.

Towed an inflatable dinghy the entire trip. 7'6' Achilles.

Twice across portions of the Gulf of Mexico, Twice across the Gulf Stream, Twice across the Great Bahama Bank, twice across Tongue of the Ocean.

I had trouble with the dinghy ONCE in the entire time, and that was due to it being under inflated, without me being aware of it. Coming off a wave, bow dug in and folded under, instead of riding up and over. Pumped it to proper pressure and no more problems.

Prior to that I did two trips from Texas to Florida, once on a 21 footer. Both times partially offshore, towing a 6'6" pram style hard dinghy.

I don't really LIKE towing but the hard fact is that on a small boat such as you mention ( and the kinds I sail) there's really not a whole lot of choices- there really isn't ROOM aboard to put one. So I tow. I also accept the fact that if the "stuff" hits the fan, the dinghy back there is expendable, if needed, to keep the big boat out of trouble. Fact of towing, particularly offshore

Currently have another 6'6" Pram under construction (B and B Yacht Design MiniPaw) which will be towed every where I go on the boat.

Dinghy looks like this. That's the 25 footer, which I no longer have.