Andrew
We live in New Brunswick and have sailed your area in summers for almost ten years. You can go from where you live to Halifax as "a series of day trips". Start by heading east up to Jonesport, go into Roque Island, yes, go through the Petit Manan Bar (it is very well marked) and go up into the north cove on Trafton Island. Spend some weeks exploring there. Once you get up past Jonesport and Mistake Island go to Cutler, then on to Eastport ME. From there, go the short distance inside to Saint Andrews, NB and clear customs into Canada. (When going home - clear at Eastport ME - their Customs / Homeland Security people are the friendliest and nicest we have met anywhere. Do some serious whale watching ten minutes off Head Harbour on Campobello Island. Head Harbour to Black's Hrbr is only 8.3 nautical miles, Dipper is only about 20 nautical miles, Saint John is only another 18 nautical miles. And, anytime you are sailing in the Bay of Fundy we have the friendliest "traffic controllers" called Fundy Traffic. They are on VHF 12 and 14 (depending upon what part of teh Bay, and you only call them if you want to. If you call them, they want to know who you are (boat name) where you are, where you are going and your ETA. They will tell you of any known traffic and ask you to call in at the next check point. They keep you informed and are never intrusive.
If you can sail the Maine waters - you can sail up to New Brunswick and Nova Scotia. Lots of harbours, lots of places to visit, no long passages needed.
Let me know when and we'll do all we can to help. PM me if you want more info.
Rik
