Are you planning to sail directly from Newfoundland to the British Isles/Scandanavia or to go via the Azores? If the latter you have several options: -
From the Azores sail slightly south of east and make for southern Portugal or Spain, its relatively warm, has several marinas with large liveaboard communities which are also fairly cheap (Lagos, Portimao) or alternatively, Alvor just west of Portimao offers a safe winter anchorage; the down side is that if your plans for next year are Ã¢â‚¬ËœnorthernÃ¢â‚¬â„¢ Europe, youÃ¢â‚¬â„¢ll have a long windward beat up the west side of Portugal to get there; perceived wisdom is to either set of early in the season or go via the Azores.
Option two would be to sail slightly north of east from the Azores to NW Spain/SW France, this wouldnÃ¢â‚¬â„¢t be as warm and will be a lot wetter, but it does save you a 600 mile beat next spring. There are livaboard communities in La Coruna/Bayona in Spain or Rochefort/La Rochelle on the French coast, alternatively the Rias of NW Spain or Hendaye/Arcachon in France will provide bullet proof anchorages.
A bit further north again will take you to Brittany in France, this gets you the top side of the Bay of Biscay so youÃ¢â‚¬â„¢re well placed for next summers cruising and the temperature doesnÃ¢â‚¬â„¢t step down again significantly provided you stay south of the Pointe de Penmarche (47.48N) A choice of marinas (Vanne, Concarneau and LÃ¢â‚¬â„¢Orient are personal favourites) or safe anchorages in the Gulf de Morbihan or up the rivers from either Benodet or LÃ¢â‚¬â„¢Orient.
The north of Brittany and English Channel are cooler/wetter still, though IÃ¢â‚¬â„¢m theyÃ¢â‚¬â„¢d still be considered fairly mild by Newfoundland standards. There are plenty of pleasant harbours and marinas to choose from on either side, or thereÃ¢â‚¬â„¢s the Channel Islands in between. As a general rule the marinas on the French side will be cheaper, though thereÃ¢â‚¬â„¢s no language barrier on the British side of the water, which is helpful if you want to work/earn over the winter. We actually spent one winter living aboard in central London which was lots of fun and whilst relatively expensive; this cost was more offset by the easy availability of well paid work. For anchorages IÃ¢â‚¬â„¢d suggest up the rivers Rance or Seine in France or the Tamar and Truro on the English south coast.
You could head further north still, but need to be careful as once you start going up the North & Irish Seas you quickly reach Scotish waters and things then get really grim. Ravaging wolves and feral haggis, an insurmountable language barrier; weather wise its freezing cold, pouring rain and howling winds Ã¢â‚¬â€œ thatÃ¢â‚¬â„¢s just in the summer, I dread to think what winterÃ¢â‚¬â„¢s like! I have some charts of the area though theyÃ¢â‚¬â„¢re not very detailed, mainly warnings along the lines of Ã¢â‚¬Ëœhere there be dragonsÃ¢â‚¬â„¢