Yes. The Kiwis and Aussies love good ocean sailing yachts. I was married to a Kiwi with a boat in Auckland and we sold it very quickly for the $$$ we wanted.
Angelo Lavronos Compass 47’ center cockpit. Fabulous boat to double hand.
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Nauticat 44 is a good boat. I’ve sailed the PNW for a number of years too, and understand the value of inside steering! Wouldn’t want a Colunmbia 33 or other open cockpit boat without a serious snow-shedding cover! I never traveled with guests, so the 26 footer was big enough for me and the hand-tools for my hobbies.
Late 50s on Kwaj would have been ‘spook stuff’ indeed. Russian and Chinese spy ships and all that. Post WWII it was the HQ where the scientists and engineers lived and worked on the A-Bomb testing for Bikini, Eniwitok and other ‘events’. I was there post-Star Wars weapons testing – which was also spy-active I understand. When I was there, Space-X Falcon rockets were being tested, the occasional Army long range missile stuff, and we had/still have the world’s largest radar installation used for all sorts of things including detecting foreign missiles, aiding the Space Shuttle and more. I worked for Kwajalein Range Services, a ‘holding company’ for Bectel and a couple other firms who got tired of outbidding each other for the right to run the civilian side of things for the Army – schools, water and power, hospital, entertainment, radio and other services. I spent my years there as one of three Technical Writers.
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What a grand adventure! Sounds like you have it all planned out pretty well. Best of luck on your voyages, Sinbad! 
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We are in the gulf coast of Alabama near Gulf Shores.
Best of luck to you! We have over the past 2 years considered selling all of it and living a less stressful life style, but we are in it for the subsidies at retirement… so at 55 we have a ways to go! But we too sold one of our larger properties 1300 miles away late last year, and bought a condo closer to us to eliminate any mortgage debt and set ourselves up to be able to weather dry periods. We now have very low overhead and do not need our properties to produce the big numbers that our 13 person cabin did, because it had a mortgage in a county that was trying to price STR out by doubling property taxes. So far it was a good move, now we just need to ward away hurricanes.
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Good for you @NordlingHouse! My wife was a liveaboard, and I paid for 7 years of PhD studies by delivering sailboats around the world. My wife and I are now looking to spend 2-3 years sailing out around 2026, exploring Newfoundland and the northern Atlantic coast of Canada, then going across the pond to spend a year in the Med, then hopefully fun-racing back across the Atlantic.
If you consider going to KiwiCountry, make darn sure you pick a sound oceangoing sailboat, if possible one that can go on a reef and survive. Having sailed tons of sailboats, for Pacific adventures I’d always recommend aluminum. Pacific cruising stats are that, any given year, 1 boat out of 3 hits a rock. No Catalina, Hunters, lower-end Beneteaus or Janneaus etc.
A few years ago I saw Sayula II, the old Whitbread-winning Swan-65, slowly going to rot in Acapulco harbor with no care. Old but very sound, although fiberglass—if you are a fixer-upper this kind of boat would probably go for a song and give you amazing adventures. Good luck and do tell us about them!
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I was “dock crew” for friends who did the 2015 ARC when it ended in St. Lucia and what a party! I’d love to do that - either direction!
Swan, Compass, and some Jeanneaus are great boats. Columbia as well. Also Baltics.
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I sailed quite a bit on an Ocean 71 Whitbread racer. I just loved that boat (what a beast) and of course the best sailing is in and around San Francisco! My bf was the 1st mate and chef and we took tourists out under the Golden Gate. We would board them and of course they thought they were going on a fine evening drinks cruise. Ten minutes later all sails were up, and the rail was buried as we scorched past Hurricane Gulch in Sausalito!
Really a boat is only as good as her owner and how much respect they have for the sea. I’ve seen “unseaworthy” boats in very faraway ports!
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Those 71+ maxis are quite something, especially with their racing rig on! I’d probably take out the top quarter before single or doublehanding them in rough weather 
I did the San Fran Big Boat Regatta in 2007 on an IRC 73’ TanTen. Short rig so this pit gal had only 85’ of mast halyard! The spinnaker was over 1,200 sqft - the size of my apartment at the time.
Fun fun fun!
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Second Life, the Ocean 71 was beautiful inside and out, a yawl that had been impounded and wrecked by the feds for drug running after her racing years, then renovated with no expenses spared. We took her out to the Farralones, but (sadly, for me) it wasn’t rough that day. I loved driving her with the spinnaker up through Raccoon Straits!! She had been re-rigged, it must have not been right to her original strength and design, because she cracked in half and sank to the bottom in the Caribbean about 3 years after I was aboard her. Very very sad. She was a well loved yacht and the pride and joy of her owner.
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One of the most interesting compliments I’ve ever heard was about a sailor.
Gene-Grizzled, no nonsense commercial captain. Licensed for small cruise liners. Later in life was a private yacht captain. 50 ft Viking sport fisher.
Boat dock neighbor arrived. He had sailed his 30 ft live-aboard from the Caribbean (900 miles).
Gene, “That is a brave man to sail alone that far. That’s an iddy-biddy boat to sail in that great big ocean.”
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You were on Second Life: that’s a Dijkstra (spell?) design! The guy also designed that whole line of giant sailing cruise ships, quite a unique look. Funnily enough, Second Life was a competitor in the same Whitbread that Sayula II won and where Pen Duick VI had to quit a leg twice. I think that Second Life did pretty well in that race! I had no idea she had ended up breaking up and sinking, what a shame 
EDIT: I was wrong, not a Dijkstra design. I associated his name with Second Life because he was sailing it when it got dismasted a year or two after that Whitbread race. He did not start his design career until later.
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Written August 24th 2011
73-74 Sayula 2 was the winner (32-80’ racers were allowed)
Second Life - Roddie Ainslie’s Ocean 71
Roddy Ainslie writes: “Second life was used as a sort of poor mans charter boat for a year or two after the 73-74 race then finally sold to an American who spent a fair amount on the interior, some new sails etc and then the new owner cruised her around the Med for a while. She was later seen moored in Chesaspeake Bay. The next time I heard of her was some years later, it was rumoured that she had been sold by the American Government having been caught drug running. ( It was in this in between time that I sailed on her 2x weekly in San Francisco) Then about five (@2011) years ago I understand she sank in the Caribbean having taken on a lot of water very suddenly, Fortunately no one was hurt.”
I think the owner I new kept his elderly mom aboard, but she had passed before the sinking. Second Life was gorgeous and strong when I knew her but they had changed the stern to be shorter and the rig was different. I think the original design could not support long term what they did.
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Well, that makes me confident! I’ve had the bow under the wave moment, when the skipper yelled “cut that spinnaker halyard NOW!”
This was Sea Explorers (senior Boy Scouts in boats). The boat was an old Bristol Bay double-ender gillnetter with keel and cabin added. Our budget spinnaker was IIRC 3 wedge sections of an old US Army parachute.
From our marina, the winds were from the south most days in the summer, so we spent hours tacking the mile wide fjord to get to the entrance, ten miles from town. That morning we were lucky, with a nice 12 knot northwest wind, so we could head straight down the channel, wing & wing, and into the intersection of Gastineau Channel, Favorite Passage, Stevens Passage, and Taku Inlet.
That intersection is notorious among boaters in my hometown. The 7 glaciers in the Taku River valley can generate huge gusts from afternoon downdrafts off the icefields, down the glaciers, and into the main river valley, where folks love that they blow away mosquitoes right around the time folks who own cabins there want to have dinner on the deck. OTOHolks trying to troll the inlet for the salmon heading up the river to spawn
Those same winds can cause havoc in the inlet, where winds can come from all four directions! What happened that day was that as we exited Gastineau Channel, the north wind dropped to about 2 knots, so of course we put up the spinnaker. About a third of a way across the inlet, a 40 knot gust suddenly appeared from our port side, and she heeled over with the bow down. I was sunning myself on the foredeck when it hit, and was upright instantly.
It was right about here: 58.20626, -135.3884
This being Sea Scouts, the skipper, a Coast Guard CPO, wouldn’t let us aboard unless we were had a folding sailing knife (5 inch blade + a fid) on a lanyard attached to our belt. When he yelled at me in Command Voice, I had it cut in 2 seconds although it seemed longer than that as the bow came back up.
I’ve never been aboard an untied boat without my sailing knife, especially after a friend drowned when the line from his crab pot twisted around his ankle and pulled him under, about 20 feet below the buoy. It was 300 feet offshore from his house, and by the time his wife noticed that he hadn’t come back with the Dungies and saw the empty skiff by the buoy that she got neighbors out. If he had had a knife on his belt he’d still be winning senior class marathons today (our local marathon is named after him).
Knives save lives.
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I wear cargo pants when sailing or racing and have a multi-tool on my belt and a folding knife with a fid in a handy pocket. Sail tape in another pocket, racing rules in the outer flap of my dry bag, and my PFD close by if things go sideways quickly.
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A 3 story house (including basement) with 40 years of STUFF. And I can’t find a Marie Kando type nor a regular holder of garage sales who knows local pricing to come help me sort & tag stuff, and I’m willing to pay. Realtor won’t show the place until it’s empty.
Revere Ware pots, silverware, a barful of glassware, about 4000 books (40 years of collecting). Rather than haggle and wait for power tools to sell, most of them went to our local Makerspace, which freed up basement space immediately.
It’s not just giving up the 83 year old family home, it’s giving up my beloved collections that let me generously loan books, host joyous celebratory dinners for 16, and let me maintain and enhance the house.
Downsizing from 3000 sq ft to an approx 45 foot boat is not going to be easy.
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I started giving stuff away once I decided I was going to retire (8 years ago). I refer to it as deaccumulating. I even had a concerned friend ask about my health and mental state since giving stuff away is seen as a precursor to suicide.
Still, I have way too much stuff. And my brother in law is sitting on a house full of my his and my sister’s stuff. My current plan is to have an estate sale company come in and clear that place out when the time comes and I’ll take a few truck loads from here to there then.
I envy you coming up with a plan to downsize now while you still have the strength and wits to do it.
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When I started living most of the year in Mexico and renting out the Canadian house, I had to empty the house of 20 years worth of accumulation for myself and 3 kids. I gave away a lot (my friends all have things in their homes now, from furniture to plants that used to be in my house, which is kind of cool), had a garage sale (more on that later) then packed up the rest and stored it in my daughter’s basement.
I’ve never been a collector/ hoarder type, but it was still an incredible amount of stuff to deal with.
Every summer when I went up to Canada, I sorted through it all again, bringing a few more things down to Mexico each time. But what I found when I went through it each summer is I found myself thinking, “Now why on earth did I bother keeping this?” So the pile kept gettiing smaller.
Then my daughter moved and I had to move all my stuff to a friend’s basement.
If you haven’t seen or used something in a year, you start to wonder why you wanted to keep it in the first place.
And it really does feel good to pare down the possessions. Lighter. It’s hard at first to part with things you’ve had and loved for years, but it’s quite freeing.
Consider just advertising on Craigslist or something. I’ve found garage sales to be more of a pain than it’s worth. The garage sale crowd for whom that seems to be a regular weekend activity are like annoying guests. Some show up and knock on your door an hour before starting time, they paw through stuff, make a mess, ask questions, then leave buying nothing.
The ones that really irked me were those who would pick something up off the ‘misc. small cheap stuff’ table, ask how much I wanted for it, I’d say “a buck”, or even 50 cents, then they’d put it back down again.
If you aren’t willing to pay a dollar for something that caught your eye, why even ask the price in the first place?
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Downsizing does feel good! Most of the items I never miss, although I’ve regretted giving that Dremel kit to the local Voc Ed school, and bought a new floor jack to take care of a flat on my British roadster right after I sold mine (I’ll never work on that car, I’ll hire it out, I thought.)
I live in a diverse area, and found that bargaining/not bargaining at my yard sales seemed to be culturally related.
It was anthropologically interesting. One group would pick up one thing and offer a somewhat lower price, another group would offer a ridiculously low amount that was obviously meant to get negotiations going and not be taken seriously, and another group would pile up a bunch of items and ask for a discount for buying multiples.
In my latest clean-out, I’ve sold stuff on eBay, which involves no direct human interaction other than saying hello to the post office workers, and what was too heavy or large went to the curb or on my freebie table at the end of the driveway. Recently I’ve joined the local Buy Nothing group.