Livaboard, moving from the dock to the hook

[SURV69]

I've lived on my Newport 28 for the past two years ... at the dock ... May-November.

I do plenty of sailing ... on other boats. I've never been confined to my boat's deck and interior ... ONLY.

I'm considering the move to actually staying on the boat year round and sojourning to warmer places for the winter.

My plan was to traverse from area to area(a few days at a time), staying at marinas for a month at a time(to get a monthly rate), before moving along.

I tend to get a little queezy at times while inside a rolling boat and I'm afraid this might be a problem with my intent.

My boat of choice will be a Bristol 29, full-keeled with nice side decks ... a little small, but then I'm only one person.

I'd like to hear how others have had to cope ... or learned to cope when they first attempted to stay on the hook. I wonder how often, a sailor learns that staying on the hook, just isn't in the cards for whatever reason.