Shipmate Otto, who endured the Long Island Trip with us, asked how the Bahama trip compared. So I'll take a stab at leaning the two trips against each other to see what stands out.
First I want to be fair to the Pearson if I can. It wasn't the fault of Osprey that she leaked like a screen door and many of her systems needed serious TLC. Also, the lack of an auto-pilot was a huge detriment over a long sail. Helm watch on Quetzal was easily handled. One could get something warm to drink, sit comfortably, take some time to gaze at the stars and the horizon, chat with whoever else was in the cockpit. Standing at the helm of Osprey was constant work and often long hours of intense concentration.
Quetzal was being sailed by her owner / master. There was nothing about that boat John K. didn't know. He could talk a crew of amateurs through setting a whisker pole in bouncing seas or pulling onto a completely unfamiliar dock in stiff winds and running tides, all the while sounding like he was giving instructions on how to start a toaster. Osprey, on the other hand, was somewhat unfamiliar to John H. and had, (in my opinion) a completely inadequate set of sails and sail controls for what we were doing. Also, (just in my opinion) we didn't do the boat any favors by filling the bow tank with almost 1/2 ton of water we didn't need. I suspect that alone accounted for about 50% of the snot that got beat out of us. The upshot is a huge part of the difference in the trips was that we went to the Bahama's on John K's boat with John K. We went around Long Island with Instructor / Captain John H. on a training boat.
To be honest, on any big scale the boats aren't really that different. The Pearson is 35' long, just about 75% of the Kaufman 47. At 13,000 lbs the Pearson displaces about 62% as much as the Kaufman. Neither boat is particularly large for an ocean going vessel and, moored side by side in a marina full of boats, they wouldn't look that different to a land-lubber's eye. I have to say I feel the Kaufman is much more user friendly when out of sight of land than is the Pearson. Still, both are "classic plastic" monohulls of less than 50 feet, a couple of decades old, designed and built by people and companies with good reputations. They are much more the same than different.
Both trips suffered a bit from being run on a schedule, and thus were not quite the same as living aboard. We shoved poor little Osprey around Long Island with little regard to waves, wind or crew fatigue. The 24 hours to Block Island took 36 and we were all pretty much knackered after a night of 10' following seas. It never really got any easier. Pushing hard we still ended up a day late and had to leave at 0300 on that last day to make Tom's River at a reasonable hour. No cruising couple I have ever heard of would trash themselves like that on purpose. (Deb and I have no intention of being any different.)
Quetzal didn't struggle quite as hard. Still, we crossed the Gulf Stream twice during a week while, (we have since discovered) hundreds of cruisers waited in FL for better weather to head east. We left West End for a questionable run to Lucaya, couldn't get into the harbor, and sailed back to the West End. On the one hand it was exactly what I would expect to do on a trip where Deb and I shelled out some serious denaro to sail. On the other hand a cruising couple wouldn't bash through 6 - 8 foot seas just to spend 8 hours away from a dock they were going to pay for anyway. Not when the alternative was spending a day sitting on the beach in the Bahamas. On the next try we made it to Great Stirrup Cay long after sunset, setting the hook after making a night run into the bay using the Chart Plotter to miss the rocks. (I would have loved that but missed the fun; holed up below fighting off my normal "3rd-day-out" bout of sea sickness.) During the process we managed a fright by almost getting too friendly with a cruise ship tender who wasn't showing a lot of light. At daybreak the hook started to drag and we bailed out having barely seen the sun rise on Stirrup Cay. Again, perfect for getting experience but something any of our cruising friends would have avoided with a little planning and patience.
In the end the trips seem more like book ends. We managed to get cold and wet on both. We learned a lot about sailing on both. (I even managed to feed the fish on both.) Sailing down the East river through the heart of NYC is about as opposite a thing to tossing a hook in Hoffman Cay as one can imagine. Yet each was fantastic and I intend to do them again as many times as I can manage. Indeed, it is not hard to imagine that a trip around Long Island and a subsequent run from FL to the Bahamas will, one day, just be two ends of a year's worth of traveling aboard Nomad II.
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