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This winter has done us in. In a couple of years we will be ready to retire and as much as I love Lake Michigan, it is now frozen and that doesn't work for sailing. Where in a warm would anyone suggest we retire with our 35 foot cruiser to be able to sail most of the year? South Florida?
 

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I recommend SW Florida. Good weather, not TOO crowded, good services...and still relatively affordable.
 

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Just about anywhere on the northern Gulf coast from New Orleans to, say, Panama City is nice. The closer to New Orleans the better the food is ;-)
On an 'out of the frying pan into the fire' note, you need to think seriously about hurricanes down here where it's warm.
 

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Anyplace where the average temperature is higher than your age - at least that's my dream. I hate this winter more than any I've experienced in my 73 years on this planet. Next winter, Marathon Key, Florida for January through March, then back again with the boat in October through March. The older I get the colder I get.

Gary :cool:
 

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This winter has done us in. In a couple of years we will be ready to retire and as much as I love Lake Michigan, it is now frozen and that doesn't work for sailing. Where in a warm would anyone suggest we retire with our 35 foot cruiser to be able to sail most of the year? South Florida?
I've been thinking the same thing, with my boat on the hard in Milwaukee for 6 months. I've looked closely at SW Florida. The waters are interesting but there are so many many miles of 3' water. Intercoastal is just a narrow string of markers. Outside might be nice, but my favorite areas of Lake Michigan are beyond 15 miles from shore, where the depth exceeds 400' and the fishing boats are all out of sight. I'm not sure that happens much around Florida.

One thing I've found helpful is to cruise the coastline with Google Earth or satellite view on Google Maps. Not only can you see where the marinas are, you can see the channel cuts and the population areas. When working up and down the coastline you can see which marinas are all power boats and which ones have a lot of sailboats. If there is nothing but power boats in a marina then you can guess that there will be very shoal water about, probably a bridge or two, and not a lot of sailors to hang out with in the local bar. Sailboat dominate marinas are pretty rare but there are a few. Also, if your boat is not shoal draft then you're going to need a different boat.

GTJ
 

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I've been thinking the same thing, with my boat on the hard in Milwaukee for 6 months. I've looked closely at SW Florida. The waters are interesting but there are so many many miles of 3' water. Intercoastal is just a narrow string of markers. Outside might be nice, but my favorite areas of Lake Michigan are beyond 15 miles from shore, where the depth exceeds 400' and the fishing boats are all out of sight. I'm not sure that happens much around Florida.

One thing I've found helpful is to cruise the coastline with Google Earth or satellite view on Google Maps. Not only can you see where the marinas are, you can see the channel cuts and the population areas. When working up and down the coastline you can see which marinas are all power boats and which ones have a lot of sailboats. If there is nothing but power boats in a marina then you can guess that there will be very shoal water about, probably a bridge or two, and not a lot of sailors to hang out with in the local bar. Sailboat dominate marinas are pretty rare but there are a few. Also, if your boat is not shoal draft then you're going to need a different boat.

GTJ
I live in SE Florida. Plenty of 400' of water around here. But know this, ocean deep water is *VERY* different than Lake Michigan or Great Lakes. Yes, the Great Lakes can get snotty, but there is just *NOTHING* that compares with ocean swell, Gulfstream Currents, and a NE winds pattern.

I'm all about protected bay sailing when I can get it. In Florida, that means Biscayne Bay, Tampa, and Charlotte Harbor. Great sailing and plenty of space to do it.
 

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My idea of retirement is an easy condo in the north (New England) to spend summers and live aboard down south in the winter. This way, I don't have to pick just one southern location and I still get home to see family and friends.

While I never really enjoy putting the boat on the hard for the winter, I'm usually starting to wear out from the constant chores. Then, by now, I'm dying to get her back in the water. It would be nice, if that break was only 2 - 3 months, instead of 5. I'm sure, if I had access year round, that I would bore of it from time to time. However, I wouldn't mind finding out. :)
 

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The best location for sailing is Biscayne Bay and the Keys. Lovely sailing, clear water and easy access to the Bahamas.

However, you have to understand that for 5 months of the year you have to be on hurricane alert and constantly be available to secure the boat for hurricane conditions.

Coconut Grove Sailing Club, Coconut Grove Sailing Club is a great place to keep the boat but if you fail to evacuate the boat for a hurricane you loose your mooring rights.

Without a good hurricane plan you have a significant risk of loosing the boat. CGSC had 50 boat destroyed or badly damaged in the 2005 hurricane season.
 

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My idea of retirement is an easy condo in the north (New England) to spend summers and live aboard down south in the winter. This way, I don't have to pick just one southern location and I still get home to see family and friends.

While I never really enjoy putting the boat on the hard for the winter, I'm usually starting to wear out from the constant chores. Then, by now, I'm dying to get her back in the water. It would be nice, if that break was only 2 - 3 months, instead of 5. I'm sure, if I had access year round, that I would bore of it from time to time. However, I wouldn't mind finding out. :)

I have thought about something like this too. Seems like the best compromise, but a long slog back for most boats, maybe not yours.

Greg-

I love the water access, especially in the keys but I get a sort of claustrophobia if I am in Florida for too long. Mountains, lakes and big rivers start calling me. Hard to trade those for views of concrete overpasses and strip malls.

This is a terrible winter. For me, it's life changing. It seems like with the jet stream curving around so much we in the North East are now vulnerable to polar vortexes in winter and Hurricanes in summer.

If you figure out the perfect answer let me know.
 

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I can't imagine someone who loves cruising on Lake Michigan would find Florida to be all that great in the long run. Talk about worlds apart. I've sailed and been on the water in Tampa Bay and Sarasota Bay and don't find it all that interesting, on the water and shoreside. Too congested, boring landscapes, condos everywhere, the opposite of pristine. I couldn't give up the northeast permanently for that.
 

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I can't imagine someone who loves cruising on Lake Michigan would find Florida to be all that great in the long run. Talk about worlds apart. I've sailed and been on the water in Tampa Bay and Sarasota Bay and don't find it all that interesting, on the water and shoreside. Too congested, boring landscapes, condos everywhere, the opposite of pristine. I couldn't give up the northeast permanently for that.
Seeing as the main reason for relocating is a warmer climate, that might be something the OP is willing to accept. Being in the FL panhandle, and having sailed in the St. Pete/Clearwater area, I think that area would be a decent choice. It doesn't look as if the water is as skinny as the Ft. Myers area...but you are still close enough to the Keys to get down there relatively easily. It is nice being able to sail year-round...although we've had some cold spells here as well...
 

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I recommend SW Florida. Good weather, not TOO crowded, good services...and still relatively affordable.
Yeah, I have a couple of places on the west coast of Florida kind of staked out.

Bradenton is one of them. But, that would just be for summers. For winters, there are better places farther south. :)

Just skip what I call the spoiled rich coast from Ft. Myers to Marco Island.
 

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I'm with Minnewaska on this one. A base in Narragansett Bay, Buzzards Bay, or Eastern CT provides good sailing and access to interesting communities and occasional trip east to ME. My wife and I met a British couple in CT who had been cruising the Long Island Sound for eight summers. They appreciated the warmth, relatively low cost, diverse ports, and good access to shoreside transportation when guest flew in.

The weather in these areas is pleasant more the year than further south. For example, Washington, DC has 23 more days per year over 90F than NYC and NYC has four more days less than 32F. Aside from the heat and humidity, many southern locations have significantly more exposure to hurricanes and tornadoes.

About 10% of the retirees with cruising boats in my local club go south for the winter. Some winter in the Bahamas. Some in the Keys. Some go outside. Some go inside. It seems a bit of a grind to me but some continue into their eighties.
 

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I'm (unfortunately) many years away from retirement, but an idea I've been kicking around is to have two boats, one in the north for summers, and one in the south for winters. My northern boat would I think be in Grand Traverse Bay, and the southern boat anywhere warm, likely Florida and close to the Bahamas. The southern boat would be the "big" boat that we'd live on, but for Grand Traverse Bay, I'm thinking perhaps a Catalina 30 or equivalent with a condo or apartment to actually live in.

Perhaps I'm pipe dreaming or not considering all the ramifications, but I love that part of Michigan and would love to have that as my summer sailing venue.
 

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Is this where we all expound on the virtues of our home waters?

I'll recommend North Carolina. Great protected cruising grounds with interesting towns to visit and countless quiet anchorages. Friendly people, southern home cooking, and good seafood. Four seasons but with a mild winter - bundle up and sail all year. Easy to head a little farther south for a month or two during the coldest part of winter (which you'd consider balmy anyway if you're from the Great Lakes) and/or a little farther north during the heat of summer or hurricane season.
 

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The O/P it seems to me is looking to move his land base from near Lake Michigan to a warmer climate which will allow him to sail 12 months a year. I think if he wanted a summer venue and a winter venue, his summer venue would be Lake Michigan but that's not what he's asking.

There is plenty of good sailing around Florida but where depends on the type of sailing he wants to do - day sailing only, day sailing with an occasional overnighter, short cruises of a week or so duration a couple of times a year or long cruises of a few months.

Then there is the cost of the land base dwelling and marina costs.

Weather is always a factor. Lowest temperatures in winter and highest in summer. What are you going to do in the event of a hurricane threat?

There is also the cost of relocating the boat and its suitability for the location chosen. Deep draft boats while fine in Lake Michigan are not so suited for Florida waters.
 

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If you've lived through winters and might still enjoy the odd winter activity like skiiing, then the PNW makes sense..

Incredible summer cruising grounds, off season sailing possible, winter sport accessible without really 'living' in winter conditions, in fact one might ski in the morning, go for quick sail and finish up with a short round of golf on some days in Jan - March.
 

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I would think if the question is where warm to retire on boat verse where warm to cruise on a boat, then the answer becomes just where best to retire to that has access to the water. It becomes more about taxes, health care access, and quality and cost of life.
 
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