Good morning from Florida! I am in a somewhat similar situation as you, except a few levels lower. At 47, I recently sold an investment warehouse, and still have a few residential and 2 commercial
properties that I will try to sell over the next 3-5 years before the real estate market blows up again. My 2 kids
are 15 & 17, so both will be off to college in 3 years with funds already set aside.
Although I currenty own 2 boats, a Mastercraft (for freshwater)and a Proline(for saltwater) for diving
, I dont have any real sailing experience. I have been certified in scuba
since the early 90's and regularly spearfish and go fishing
off shore 20 miles or so and in the keys every year.
Here is my plan so far. I say that because it has changed and keeps evolving
1. Going to buy a sailboat in the 27-32 ft to learn on. I found an older 27' Catalina
that seems to be taken care of and im going to go look at it this weekend. It is under $15k, and it is big enough for my family
to stay on over night and learn this stuff without breaking the bank if things dont work out.
2. If we like the lifestyle for the next few years, we will be upgrading in 2-5 years to something in the 38'-42' range to cruise
the carribean semi-retired. I also like the Beneteau
boats, especially after watching la Vagabonde videos, and found a great deal on a project Beneteau
here in FL. If I wasnt married, I probably would have already wrote a check for it, but it's a lot bigger and still needs a lot of work and I feel I would be over my head
vs getting out on the water
3. Get everything sold and learn to sail around FL over the next 3 years. Maybe even take an ASA
course as well next year. In fact, if you want to come to FL, we can try to take it at the same time. Get certified in scuba
and ill take you diving
while you are here. Make sure you are going to like diving, some people dont care for it after they get certified. I have outfitted my entire family
with good 2nd hand gear
from people that decided it wasn't for them.
Anyway good luck in your endeavors and if you want more info on FL, scuba, etc. Feel free to reach out.
Also if any one has suggestions, I'm open to it!