22 to 24 for new couple
I cut my teeth on a Catalina 22, and I recommend them. I don''t think you can go wrong there. But the Windrose looks to be a fine boat as well, and may offer a bit more room for weekending if you''ve a mind. What choices you have will depend on your local market more than any other factor. But you should have many options in this 22-25'' trailered entry-level boat category. This is a good choice for couples new to sailing who want a dry ride. A swing-keel trailerable offers a good combination of responsivness, comfort, forgiveness, and versatility, and there''s always a resale market when you''re ready to move up.
One caution for any new boatbuyer: the condition of the sails will affect your offer: even used, sails are costly components of your vessel. Inspect them closely and tug hard at the stitching. The sun''s UV will deteriorate the the threads, and they will eventually fail under load. There''re fewer sickening sounds for a sailor''s ear than heeling under a gust and hearing your sail "unzipping" over your head as the seams let go. The mainsail has a shorter life than the jib, so it should receive the majority of your attention.
Insist on taking the boat out for a sail, and if the owner balks, tell him you''re looking at another boat whose owner has agreed to a sail. If you know enough to do it, while at the dock, raise the main and tighten all sail controls, and see if the bottom third of the sail is baggy even when "flattened" (or just pay attention to how the sail hangs when not under pressure, i.e., while motoring out when there is no wind, or while tacking, when the skipper turns the boat and the bow moves across the oncoming wind). A blown out (baggy) sail seriously compromises the performance (and enjoyment) of you boat, and will need to be replaced. Know how much a replacement will cost on the used market, and don''t be afraid to explain to the owner why your offer is under his asking if the sail needs to be retired.
While underway, take a turn at the tiller. Feel. If you''ve never piloted a boat before, ask the owner to teach you. It''s his sale.
Don''t rush in to ownership. Do your homework. Try to get out on some of the boats you are considering. Go down on the docks and talk to people. You''ll be impressed on the whole with how helpful and free with information most sailors are. You will probably receive offers for daysails from enthusiastic sailors. Many of the owners of larger boats have owned trailer sailers and will be ripe with experience and opinions. And if you find someone whom you deem trustworthy, or already have an experienced sailing friend, ask him to come with you to look at a boat. My first boat had many flaws that I frankly didn''t know to look for; an experienced eye would have been very helpful.
And don''t discount what the wife has to say. If she likes the belowdecks layout of a certain boat, or its motion while underway, it will be difficult to dissuade her.
Enjoy the process.