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You 're going to very dependent on the weather (as opposed to the climate!). If the jetstream is going to the south of the UK, you can easily get prolonged periods where low pressure areas roll in every 48-72 hours. The South West coast of Ireland has masses of beautiful places and plenty of shelter - but if you can only move once every 3 days, it 's a bit limiting. On the other hand, if the lows are blocked by a high pressure system or heading way north, you could have the most fantastic time.
There are now many places to leave a yacht down the west coast (Dingle and Lawrence Cove being the only ones I know of), until you get around to Kinsale and Cork. The crossing to the UK would take 36-48 hours, and should be fine in a trans-atlantic boat at any time of year if you can choose when to go.
So, what you 're planning is perfectly feasible but it may involve a fair bit of drinking Guiness and waiting for weather windows!
Re the sailing season. I would say boats are being laid up anytime from the start of September to Jan, although as autumn progresses, sailing tends to be more day and weekend sailing and dependant on the weather.