This thread is super! Thanks for all the comments.
I suppose one has to begin with the fact that most cruising is probably double handed... a couple... and some
single handing... the "adventurer/loner type".
So the accommodation needs to be for probably a couple... extra berths are for guests... rare probably when one is off cruising around the world. But yet people are known to come for a passage / company.
I have a Contest 36 set up with a typical V and also large double aft. I think most owners would, as I do turn the V into a "walk in closet"... or for accessible stowage space. And for that it's provides plenty of space for single or double handed cruising. More space? For what? Perishable foods? Maybe. More elaborate
galley? Maybe.. I have a U and we can cook anything and do it comfortably in a sea way. Sure a bigger refer and or
freezer would be great... But that becomes more like a necessity for long passages... AND there are "work arounds" for that.
What you DO want is lots of tankage. And a
water maker is a great idea and doesn't take much space.
So for accommodation you want a fair amount of accessible stowage space... spares,
clothing, tools and so on.. based on your access to replenishment of same.
Then you want a comfortable dry cockpit because it is there that you spend MOST of the day. The cockpit needs to have good access to all the controls for sail handling, maybe even
anchoring... and of course data that is needed to inform sailing decisions... And if course a well laid out
helm... for when you DO have to take over from the AP.
Electronics is now very advanced and growing complex. This is a blessing and a curse. Redundancy and spares make sense. But maybe not so much a large integrated system with displays and controls all over the boat. Dunno. I'd keep it simple. But say 2 speed transducers is not a bad idea or 2 sounders. I'd steer clear of PC and tablet based non
marine systems... They are not robust enough I think for being far off from civilization. Redundant comm
equipment is a must.
Bigger has the advantage of providing more stowage and more "creature" comforts. My 36 has enough for single or two.... a bit more "space" would be welcome. The cockpit is more than adequate. You sit and you are not strolling around in a
sail boat except when sail handling or
steering... the later you will do very rarely as your AP does that.
Berthing may or may not be an issue. If you have a good
motor and dink... you'll
anchor out. And it's almost a contradiction to be a
round the world type sailor thinking you'll sail from one full
service marine to another. This means... you want great ground tackle... and a reliable dink to get you and supplies back and forth to the mother ship.. and dry as possible. Stowing such a dink is more difficult for smaller boats. Towing on passage is not an option.
I got my 36 when I was a pretty strong vigorous 38 yrs. old. Now at 69... as much as I would love the extra comfort of larger... and the slightly faster passages associated with more waterline length... dealing with the "forces"... becomes THE issue. I use a Milkwakee drill with a
winch bit to raise the 440SF main. I can do it myself but it's getting harder as I get older - FACT.
Anchoring with
electric windless means you can deal with any size ground tackle. But if the
windlass craps out on you... WOW you are going to have to find a
work around. The ground tackle alone is something that makes one think of long distance cruising a large heavy boat. When I cruised the
Caribbean, anchoring was something done more often than passage making... if that makes sense.
Having experienced a 36' for local coastal and
live aboard offshore cruising for single and double handing... with a non sailor wife... as a younger man and now as an senior.. my recommendations would be minimum 35-36' and maximum 42'. I can't
project the upper size because I simply haven't sailed them for more than a few passages... on
delivery... a Tayana47?? and a Stevens 52. Passages the larger size was great... but conditions were not challenging... so that speaks for itself.
When things go right... bigger is fine... when things go wrong (and they will) smaller is probably better.
All the stuff about bigger coming with an out of proportionate higher cost is true.
I think your age and physical condition is a huge factor in the decision assuming you have the financial resources to get any size.
My 2 cents.
PS.... I've done several single handed passages from NE to the
Caribbean... a few with crew of 4 and all the rest of the time I sail with a non sailor very helpful partner. The 36 is about a large as I want to "maintain"... THAT is hard work too.