Sounds like an adventure.
I have cruised the
East Coast of Iceland and the Scorsebysund part of Greenland, which is in the Northeast, so not quite the same areas as you are proposing, but could give some general tips.
Iceland cruising is great; the best
parts are the East and the North; Reykjavik and some other interesting things on the West; the South is forbidding and unapproachable without a
single safe harbor. There are few places with any yachting infrastructure but you can
anchor out and often find space in a
fishing or
commercial harbor. It's
remote and thinly settled (especially the East Coast) but quite civilized.
Getting there from
Europe is not too hard -- we sail from Cowes up the
East Coast of
England,
Scotland, Orkney Islands, Faroe Islands, then to the Southeast of Iceland. The only
passage of more than 300 miles in this was the East Coast of
England which we did nonstop. The advantage of relatively short distances between the islands is you can be pretty sure about your
weather windows. Which is really important because these waters at these latitudes can pack fearsome weather and sea states.
The further North you get the more likely you are to run into dead calms.
If you are trying to get to the U.S. from Iceland you will have to get around Cape Farvel which is notorious for terrible weather and sea states -- pick your weather window carefully and stand well off. There is one harbor on the whole East Coast of Greenland where you can actually
dock -- Tassilaq. If you want to see this exotic and extremely
remote place, then you get there from Reykjavik. Otherwise, sail around Cape Farvel and there are less remote harbors on the Southwest coast, which is where most of Greenland's small population live. From there make your way to Labrador etc.
Note that the East Coast of Greenland, unlike the
West Coast, is ice-bound most of the year, since the currents flow clockwise around Greenland, bringing cold air and
water down the East Coast from the Arctic. Tassilaq is pretty far South but you'd better check the ice
charts, which are published by the Danish met
service. Note also that there are no
rescue services in Greenland and you need to check in with the Danish coast guard -- read up in a pilot book about the formalities.
It is possible to do this whole trip without any really long passages so maybe possible to avoid ever being caught in really bad weather but nevertheless I would personally be nervous about doing it, in such high latitudes, in a small cat. I carried a Jordan Series
Drogue on my boat (a large, well-found mono) and would strongly recommend you do the same, but there's no substitute for really careful
passage planning and watching the weather like a hawk. I have
HF radio and Winlink but I took along an
Iridium Go for getting gribs and other weather (and ice!) info through SailDocs, and it was brilliant for that.
Let us know how you get on. My own trip to Greenland was the trip of a lifetime. It's hard to get there but worth it.