Hi Pete, thanks for your post!
Your plan sounds like an excellent idea!! Do it!!!
Lunar took to it really well, but she was very very young when she first went aboard. As a result (I think) she's very good on her feet even on moving shiny gelcoat surfaces.
But we've seen a lot of other dogs being fine on boats with varying levels of nervousness.
A very very few we've seen don't like it at all - but I suspect they'd acclimatise after a while.
So really the problem you'd have as you've identified is walks and toilets.
Walks aren't a massive problem when you're hopping around the coast really. The longest we spent at sea non-stop was about 2 days. We gave her a good walk before and after and she entertained herself by barking at dolphins on the trip. Suspect longer at sea they'd just get used to it after a bit, and be a bit miserable. We do sometimes play fetch on deck with her when it's calm tho.
But the toilet might be an issue. We're lucky in that Lunar will do 1s and 2s on deck, but Terry's dogs (also JR size terriers) won't so he _has_ to go ashore so they don't burst. Have heard varying stories from other owners. I know some have a garden tray in which they grow a mini lawn and I've heard about some chemical you can put down to encourage them - and there's some mats you can buy from pet shops which are supposed to attract them to 'go' on it. Lots of things to try.
Guess you'll just have to try it and see how it goes.
Can you take yours aboard a friend's boat or something to see how things pan out?
Let us know how you get on!

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