Question: Next May we are taking our new (old) boat on a shakedown to Bermuda and back (our home port is Deltaville, VA, on the southern Chesapeake Bay). After that, we’ve been imagining a summer voyage in the Atlantic, maybe Azores-Ireland-Iceland-Canada-Chesapeake. My question is, is there a good route strategy for this trip?
Answer: You could do the circle via Iceland in June to September but you will be pushing the season hard on both ends. It will be a tough trip and you should plan for at least a couple of gales at sea. I would not attempt it without considerable ocean voyaging experience and a boat that has been fully tested in severe conditions offshore. The big challenge with the above route is getting around Cape Farewell without getting hammered by a late summer storm or worse still, a hurricane that has gone extra-tropical.
There is another option that leaps to mind. How about a passage to Bermuda in late May or early June. Stay in Bermuda for a couple of weeks. Then passage from Bermuda to Nova Scotia in mid-June. Cruise Nova Scotia and/or Newfoundland in July and August. Return home via Maine in September. If you do all of the above along with a circumnavigation of Newfoundland, you will have 5000 to 6000 miles on the log with some ocean work by the time you get home. However, you can be flexible and, say, cut out Newfoundland if you find you want to move more slowly.
In case you do pass Iceland during your voyage. Here is one harbour you can stop by. The port of Hafnarfjordur. You can find more practical info on their english web site.
Safe journey