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I would guess Wyoming is one of the most dangerous states in a lot of stats. I don't know anyone to have succumbed to a hurricane, drowning here is not uncommon though, death by Grizzley Attack is also a possibility.
Don't forget the rattlers!
 

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S2 7.9 Bear Lake, UT
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Don't forget the rattlers!
No poisonous snakes or spiders, or even fleas here, the ground is frozen too much of the year.

I have lost more friends to avalanche than anything else, followed by kayaking, climbing, and auto accidents. Wyoming is not a safe place to hunker down. Or Wyomingites are bad at hunkering.
 

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With luck it will be two hundred years until the next bison stomping death in Wyoming.... at the "Bison-tenial"
(Hey, someone had to say it!)
:)
 

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I’m in a very similar boat (pun intended) as you. I am planning to head out mid November for my first gulf crossing. Nothing but a week of ASA certifications under my belt. If I see you out there, let’s have some sundowners.
 

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Welcome, My best advice is know the basics, all the systems on your boat, learn and continue to learn weather and it’s patterns, this is really important, don’t go anywhere without a good weather window, know how to reef your sails and when to do it. Know navigation. And remember to stop and smell the roses, have fun, We are starting our third year, and we understand what starting out is like, your going to have tales to tell in no time, from newbie mistakes, to anchoring under sail for the first time because your engine decided to stop working and chose to teach you how to do it. The adventures are frankly priceless. Again have fun!

Fair winds,
 

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Have you considered the Chesapeake? We have lived on our Catalina 42 on the East Coast for almost 2 years on the East Coast. Some insurance companies won’t cover you in Florida during hurricane season, rates improve for most if you are north of there. While we haven’t done it, we have lots of friends who head for the Chesapeake for hurricane season and start south around early October.

Even in Georgia we prepped for hurricane twice last year. We lost our foresail in a freak storm that went through the marina. A good cruising speed for most of us is 7 knots, we aren’t outrunning the storms. Pulling your canvas multiple times a year is a pain so most people prep and leave it prepped after the first storm or they head north where the storms are less frequent. Charleston bay also has decent sailing.

One newbie to another, if the prediction is for 5’ seas prep for 10’!

Best of luck. Hope to see you out there
 

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Discussion Starter #27
East Coast is in the path of Hurricanes... but the further north your chances of avoiding a bad cane improve. You might look for a weather window to move the boat to NE and sail those waters until the time is right. Lots of options in NE or even the Chessie. Making easting is not the easiest from down in FL.
Great tip! Thank you! That might also be a really good option to get some experience while we wait out the hurricanes
 

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Discussion Starter #28
Welcome, My best advice is know the basics, all the systems on your boat, learn and continue to learn weather and it’s patterns, this is really important, don’t go anywhere without a good weather window, know how to reef your sails and when to do it. Know navigation. And remember to stop and smell the roses, have fun, We are starting our third year, and we understand what starting out is like, your going to have tales to tell in no time, from newbie mistakes, to anchoring under sail for the first time because your engine decided to stop working and chose to teach you how to do it. The adventures are frankly priceless. Again have fun!

Fair winds,
Thankfully I already had the engine go our in San Francisco and learned the hard way - Good experience but I don't want to do it again unless it's voluntary!
 

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As you move up the East Coast, hurricane odds improve, but no where do they drop to zero. We just had a tropical storm come through last week. All things being equal, I’d rather be up here or the Chessie than FL. However, as I mentioned before, I think having a solid hurricane plan wherever you are is the key. A transient in the Chessie may still be exposed, if they aren’t on a haul out list somewhere or have good place to ride it out.
 

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As you move up the East Coast, hurricane odds improve, but no where do they drop to zero. We just had a tropical storm come through last week. All things being equal, I’d rather be up here or the Chessie than FL. However, as I mentioned before, I think having a solid hurricane plan wherever you are is the key. A transient in the Chessie may still be exposed, if they aren’t on a haul out list somewhere or have good place to ride it out.
Haul out is often the best recourse for a cane.
 

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A boat such as you contemplate is a complex machine. You will not want to set off until you are up to speed on all her systems. You’ll want a comprehensive inventory of tools and spare parts. Those that enjoy cruising have become self reliant and that is itself a commitment. I’d first pick a moorage in a place I’d enjoy living for a month or two and get to know the boats systems while doing some day sailing, perhaps with capable folks you meet in the marina or with an instructor. Perhaps earn an ASA certificate. Then after hurricane season, hire a skipper to help you sail to the BVIs. There you can cut your teeth in a forgiving sailing ground and learn the ropes on the way. There you will be able to ratchet up your skills and buy the things you didn’t realize you’d need. When your ready for your first journey you can make a run to Sint Maarten or St Barts. Sint Maarten is the perfect place to get those repairs and modifications done. By then you’ll be ready to cruise.
 

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I realize this is a month old thread, but I'm surprised no one has mentioned the issues cruising the Caribbean during COVID. Lots of islands are closed to Americans and even PR and the USVI have denied entry to American cruisers. The busy hurricane season is a primary concern, but there's little reason to think COVID will improve even when the weather does.
 

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Hey guys, I am in a similar situation. I just bought my retirement boat (Bristol 35.5) near Annapolis on the Chesapeake Bay. I'm not clear whether or not you guys have actually purchased a boat yet.

I would be very nervous to have a boat anywhere in Florida right now. If you have not yet purchased your boat, I would consider looking a little farther north along the east coast. Florida boats are actually ridden pretty hard and put up wet. (Lots of saltwater, constant sun and hot weather damage).

There are a lot of boats to be had in places like the Neuse River near Oriental and New Bern North Carolina, and a lot all over the Chesapeake Bay. Boats in the Upper Chesapeake, are considered more like fresh water boats, than say boats in Florida might be. There is a lot of fairly protected sailing in those areas, and the Pamlico and Albemarle Sounds of North Carolina.

In preparation for my sailing adventures, I took a week-long Cruise and Learn Bareboat Skippers course. It included a live-aboard skipper, who took us through everything from leaving the dock, sailing, anchoring, picking up a mooring ball, basic coastal navigation, timing passage against tide currents, and returning to the dock.

Any sailing school will have referrals for certified skippers who you can hire to take you out on your boat to teach you all of the specifics of how best to use your particular rigging setup, and sail configuration, and sail inventory. Doing something like that will jump you ahead a year or two, of trial-and-error learning you might do on your own.

Some sailing schools offer a course on repair and maintenance of small diesel engines.

I'm planning on spending about a year sailing my boat all around the Chesapeake Bay before my wife and I become East Coast snowbirds, moving back and forth from the Caribbean to Northern waters to follow the better weather seasons. That should give me time to really "become one" with my boat.

Just a few of my thoughts.
 

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Midwesterner, I like your plan. I've been sailing around the Chesapeake for about six years or so. Because work keeps me from sailing as often as I'd like, I've found classes in combination with owning the boat quite useful for speeding up my learning curve. They are expensive, but worth it if you have more money than time (admittedly a lucky problem to have). I've learned a lot much more quickly than I would on my own. Also, being a cautious person generally, I'm happier trying new things with a more experienced person at hand to guide me. Classes have also forced me to learn things I might have resisted, like navigating without GPS (dead reckoning) and avoiding some embarrassing newbie mistakes.

Without owning a boat to practice those new skills, I'm sure they would just depreciate. (Heck, they depreciate over winter.) And boat ownership means understanding the context of a lot of cruising course material which I think helps it sink in.
 

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Regarding the OP, although I agree the Chesapeake is a great place to begin the kind of retirement they are planning, I assume part of the attraction of the Keys for them is the lively gay community there. We don't have quite the same size community to offer in the mid-Atlantic, outside of DC and Rehobeth, neither of which are on the Chesapeake.
 

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Regarding the OP, although I agree the Chesapeake is a great place to begin the kind of retirement they are planning, I assume part of the attraction of the Keys for them is the lively gay community there. We don't have quite the same size community to offer in the mid-Atlantic, outside of DC and Rehobeth, neither of which are on the Chesapeake.
Oh, no, I wasn't suggesting that they change their plans of where to settle (although they never mentioned a plan to settle in the Keys, or anywhere. If you re-read their post, they only mentioned purchasing a boat in Florida, and then, they said, "Starting off from Florida in September 2020 for destinations unknown.").

I was only suggesting that, right now, during a time of multiple hurricanes, that purchasing a boat in Florida, could be risky. I was merely suggesting the Chesapeake Bay area as a place that has a good selection of more lightly used boats, than most in Florida, and then recommending that they linger in the area for a couple of months, to wait out the hurricane season. They didn't mention settling anywhere.

I have a gay nephew in DC, and he has friends in various gay communities all over the area.
 

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Reasons why someone should avoid purchasing a boat in hurricane areas, during hurricane season:
I bought my boat on August 8th, near Annapolis. I purchased my insurance the week before, through BoatUS/Geico. I made note of the fact, that the insurance person called my attention to one provision of my policy: Geico pays at a lower percentage rate, if the boat is damaged by a "named storm". I believe that it is double the deductible.

Two days after the boat became mine, Hurricane Laura (A named storm) approached the Annapolis area, diminished in force, but still coming with a prediction of a possible tidal surge of 3 to 4 feet. That would be enough to strain my dock lines, and put my boat up in the parking lot.

Laura blew through with just some rain and light wind, and only about a foot of storm tide surge. I got lucky, but I was sweating it.
 

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These guys (OP) have not been back on in a month and I wonder if they bought a boat, and how they are doing at learning to sail it.
 

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I’m doing something similar. Purchasing a Caliber 38 near Vero Beach, Fl. Survey in a couple days. Yes, hurricane season. Also getting used to a new and big (to me) boat, new systems, plan to singlehand as well. The moorage is paid thru october. will liveaboard, get used to her, and eventually prefer to move down to a slip in Fort Pierce. Nearby open water access, and not as shallow. That would give me the winter to sort things out, before heading north to the Chesapeake for summer. Anyone doing something similar Feel free to contact me. Lets compare notes or conversation over a beer.
 
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