Very capable boat. Mid 70's we were tied up in Kirkwall harbour one wet windy evening when there was a heavy thump alongside. One guy was hanging on to our shrouds while another was dropping the sails on a C 26. Two young Swedish guys on their way home from a cruise to the Faroese Islands. No engine, they used the engine compartment to stow light weather sails.
I sailed on one (from Barbados) in the Bequia Easter Regatta in the late 90's. Good fun, and we had a good rating, and did reasonably well.
In the race around the island, we stayed inshore, short tacking on the beat up to Bequia Head to get out of the current, while everybody else went off out into the channel, and this gamble paid off - we were the first boat up to Bequia Head, even beating 60 foot boats!
We did have 5 fairly heavy lads sitting on the rail which helped a lot - she was more like a submarine plowing through the waves, and we were all totally soaked, but the water was warm.....
Nice set of videos - I too hate the East Coast, for me the wind direction was not helpful. Interesting the use of the shock cord to steer, I presume he got the tiller pilot in Ramsgate.
The bungee on the tiller really is very effective on a Contessa 26. The hull is a direct copy from a Folkboat, which I have and have frequently used bungee to steer whilst beating, although now I'm a bit more upmarket by using 'sheet to tiller' from the boom, which works fairly well down to a broad(ish) reach. Coming down from Wick in July in +30kt winds, it worked perfectly for 6 hours so I could shelter/whimper inside!
Not just Folkboats and their clones, Most designs of that era had well balanced, directionally stable, hulls and rigs. All my monohulls had longish keels and keel hung rudders. They would just keep going upwind.
The 42 ft 8 metre cruiser/racer by McGruer was happy in around F6 with I reef in main, working jib, and deck edge just above the waterline. We have sailed for quite a few hours like that in open water before realising the wind vane steering gear was not engaged. The bungee on the wheel/tiller seems to allow just enough give in the rudder and is better than a rope lashing.
Much to my surprise I managed to get a Prout catamaran to do the same when the wheel pilot belt broke on a single handed delivery trip. She kept going on a very close reach in a wide range of wind and sea states with different reefs. I decided it was the fact that she did not heel significantly so hull and rig balance, once set up, remained constant.