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I have traveled to all the places you mentioned but only sailed in the keys. I have also visited your area.

California is has a great climate and I really like the coastal scenery. The water is cold and the Santa Ana winds can be harsh. The downsides to me are the high cost of living and large population. You should have access to the internet, electricity and females living and sailing in California.

The Florida Keys are amazing. I really like the middle keys (including Marathon). The weather is very warm in the winter (typically highs in the 80s) and the humidity is allways high. Internet access is available even on a mooring through your cell service. The cost of living is cheaper than California but more expensive than the rest of Florida. The scenery is different, lots of islands but no mountains. The sailing is great but on inland side the water is shallow so watch your charts and depth finder closely. Great fishing. I have always been married when in the keys but there seem to be plenty of women. This winter my wife and I were siting by the motel pool and a 30s woman came up to talk to us. She was hitting on me with my wife sitting there beside me (we are in our 50s!). I was flattered...

The St Pete area is very nice, my brother lives on Treasure Island, near St Pete. Great weather in the winter (highs in the 70s when I have been there. The winter in St Pete is very similar to the summer in Wisconsin. There are alot of people from the Midwest who have moved to southwest Florida. Check out the marinas in Gulfport, St Pete Beach, Treasure Island, Madeira Beach, etc. for excellent weather and access to the gulf. You will find plenty of companionship in the area. There are places to go sailing in the area and they have active sailing club activities. You can always sail down to the keys if you have time.

I think you would enjoy all the areas you mentioned. My preference would be St Pete (on the gulf side inter coastal) followed by the Keys for your situation. If you got a boat in Florida you could even sail it back to the Great Lakes for the summer then return to Florida for the winter! I don't know how practical that is though.

Thx-Ace
 

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An old sailor said to me, "We're lucky. When you get cold in the fall or winter, you can do something about it. Point your bow south, set sail, keep going until you're warm, and then find a place to drop the anchor."
 

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I have a theory that if you do not subject your body to a temperature lower than your age, you will live a long and happy life. I now consider any temperature lower than my age (77) the dead of winter. :)

If my health allows, I will be setting sail sometime around the first of October and point the bow south. I'm not stopping until the daytime temperature and my age are the same. ;)

Good luck,

Gary :cool:
 

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I would say Cali. There is so much more rugged & gorgeous coastline to see here. And the South is very warm, or if you are up for some adventure, British Columbia is absolutely stunning for sailing
 
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