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Wooden boats are especially pretty and an Alden is a lovely creature. Not sure if I'd want to actually own a wooden boat again, though, and mine was only 28'.
I've lived aboard for a couple decades, it was a good thing. On a mooring, it is nice and quiet, no people wandering past the nose of your boat, but there's the dinghy to work with all the time. In a marina is much easier for getting on and off the boat and such, but it gets pretty busy sometimes and can seem like you're living in a goldfish bowl. Depends on the marina and how folks have access to the boats, of course, though.
When living aboard, it's sometimes difficult to prepare to sail, though. Stuff gets out of where it's supposed to be and then you have to get it all organized for sailing and then when you get back from sailing everything has thrown itself to the floor. And that's usually when the bilge pump isn't working as efficiently as it should, too. But sailing is good. So is motoring, too.
When you live in a marina, there's lots of other folks that you meet that have boats (imagine that!) and they are frequently looking for crew to help them go places. A lot of times you can go places and not even need to take your own boat.
When traveling on boats, though, it's not free. We sailed from Connecticut up to Martha's Vineyard and back last year and every night we were in a harbor and all the harbors wanted mooring fees. Then there's the launch to get to and from the mooring (it was too much hassle to launch the dinghy). We were only sailing for two weeks so laundry never became much of a problem, nor mail. There is a lovely place at Newport, Rhode Island where there's showers and a laundry and a dinghy dock for folks out in the moorage. It's the old armory building there. I'm sure there's other similar places as you cruise.
So, early retirement, if it were me, I'd opt for the boat. However, while boating, keep an eye out for a land based retirement spot. If you can find one near the marina, then you can liveaboard there for several years and make friends with the folks in the marina then move ashore and still have friends with boats. Sometimes friends with boats is much better than a boat yourself.
"Now that I'm retired, we've been looking at a house on a canal that's a few minutes from Charlotte Harbor. But the cost of the house and a boat will really strap us financially"
I considered live-aboard, retired 'boating' several years ago ... thinking that we might better afford a 'romantic lifestyle' aboard, than a land-based retirement. Several things led me to choose a land-based retirement, with boating on a reduced scale as an alternative:
1). I lacked the mechanical skills (or interest) to do my own maintenance, the budget to afford to pay someone else to do everything and the willingness to risk breakdowns miles from the nearest port.
2). Actual retirement in one's 60's or even 50's is a 'no turning back' decision -- 'Investing' the majority of one's retirement housing resources in a steadily depreciating asset, could leave indefinitely far more strapped -- if the live aboard option didn't work out after a few years.
3). The idea of live-aboard, 'sail off into the sunset'-boating is more appealing than the reality of too little space; limited land-based logistics and transportation; extended damp, wet conditions; long stretches of boredom; and no home to 'go back to.'
In some ways it is easier now because of modern conveniences.
My world cruiser friends were able to be in touch anywhere in the world... they could do their banking, etc. as well as e-mail friends and family.
Their on board systems for navigation would have been unimaginable earlier and the autopilot for a 3 masted sale boat meant the husband and wife were sufficient to circumnavigate the globe.
They had almost 20 years and made friends and had so many new experiences to write a book... they also traveled with their dog bosun...
As with all things... they did make the transition to land...
By the way... he was an experience pilot and businessman and she had a career in medicine... never could have children...
I would live on a boat if I could afford and get in the Sausalito marina.
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