The problem with the question is that each of us have different needs related to sailing and cruising. And we change as time marches on. I'm now eighty-three and yes, still sailing and enjoying my present boat. However, I have had ten new boats during my lifetime. Some of those boats I bought and some I ordered from the factory.
I've had a
Cal 10, a
Pearson 27, a
Ranger 29, a
Ranger 32. Then a Scepter 36, a
Hunter 40, a Hunter 32, then a Hunter 35.5 (won boat of the year in
racing locally), next a Hunter 380 and finally a Hunter 27. I've learned a lot about sailboat along the way acquiring my 100 ton captain's
license. I taught sailing (on a variety of sailboats) and captained chartered boats.
My worse boat was the Pearson 27 followed by the Ranger 32 (ironically it is one of my wife's favorite). But take my answer with a grain of sail (seawater?) as I have sailed my entire time in
Puget Sound, the
San Juan Islands, the Gulf Islands and Desolation Sound. I never got to
Alaska but that was in my plans. I love the
pacific northwest so my boats reflect my cruising grounds. I've done no ocean sailing but have raced in 55 knots of
wind (and waves).
If I were in your shoes in
Florida and planning on
retirement, I would have a Hunter 380. Probably my best overall boat. It has a great place for the AC, two
propane tanks, good
refrigeration, a great aft
cabin with good
storage. It has
roller furling reefing, an arch, a wonderful
cockpit, and a bunch of other good stuff and to top it off it is an excellent sailing boat. Overall, it is my favorite boat. I would still have it except as I grew older (this does happen to us all), I found jumping down to
dock to the boat was getting harder and harder. It was harder to
paint the bottom. But still, it was a wonderful boat.
Today I have a Hunter 27 that fits my needs. A good
dodger (necessary in the northwest), a hot air furnace, a
Raritan PHII
head (old
men need good heads), sugar scoop stern (to get on and off),
3 blade Max prop (to back in gracefully), a two burner
stove (one
electric and one butane) to make coffee or tea and a small but useful cooker.
I love this boat but the Hunter 380 was my favorite. Best of luck on your new to you boat.