Join Date: Jul 2018
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Where to go for winter sailing? Florida or California?
I work remotely for a software company and am planning to relocate south for the winter so I can keep sailing. This is my second summer of sailing my Pearson 28 on Lake Michigan, so this winter the plan is to purchase a boat close the the area I want to spend winter in, live on it, sail as much as possible, and then either (a) keep the boat and stay there, or (b) put it on the hard and come back to Lake Michigan next spring.
I will be keeping my apartment here in Wisconsin while I'm gone, in case I decide living aboard sucks and want to bail on this experiment.
Originally the plan was cruise around the florida coast, but now I'm considering SoCal as well.
So anyways, I'm looking for 3 main criteria:
1) Warm weather obviously
2) Cool places to weekend sail to, or places where I can cruise to and still work during the day with access to internet and electricity
3) Fun area surrounding the home base marina/mooring/whatever
I'm 31, single, and would be nice to be in an area where there will be people around my age, women in their late 20s etc.
The ideal fantasy liveaboard marina would be near a beach, have a path along the water that people use to jog/walk/bike on, and have lots of restaurants, bars, and coffee shops all in a central location nearby. With lots of spots that regulars congregate at.
I don't expect to find the perfect place, but I'm open to all suggestions.
St Pete, FL area. St Pete has a year long waiting list, but there's a marina called Regatta Point nearby. Although not sure if it'll be all retirees with nothing to do around the area.
Florida Keys. There's a cheap mooring field in Marathon.
Long beach area? Not sure if there's a giant waiting list.