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
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
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.