So you are staying in Pictou before PEI? You can explore the Hector Heritage Quay and see the replica of the first ship which brought Scottish settlers to Nova Scotia. There are some wonderful beaches nearby and some interesting shops. However one night should be enough.
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http://bit.ly/2mfOrsd Trip Reports
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http://bit.ly/2libRZF Northumberland Shore (Pictou is here.)
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it depends a bit about the part before you get there (-:
it is the same volunteers that post on all the Nova Scotia and PEI forums so a suggestion is that instead of asking in each location that you use only 1 post so we can follow and keep track of your plan as it evolves as some questions might be relevant to what you are doing before and after.
If you fly to Halifax as suggested in one of the post it depends on time of arrival and where you are headed off first. Pictou could be an overnight if you arrive late from Albera and head off there first instead of going into Halifax - you could then spend the day exploring the town - then get on a late ferry to get to the cottage you might find in PEI
Most people if exploring both pei and cape Breton in the same trip will take the confederation bridge to get to pei and then leave pei they take the ferry and drive to cape Breton, this saves doubling back. Something to consider.
The answer to your question for me depends on what time your flight will get in. I would want a couple hours to explore the Pictou waterfront and have a meal, either in the evening or morning. If you flight lands early afternoon I’d drive there and explore that evening then catch the ferry the next morning.
Our plan is to fly into halifax, make our way to PEI, confederation bridge to New Brunswick, ferry to NS, tour NS and up to Cape Breton for Celtic Colors Festival(at beginning of Oct) , back to halifax to fly home. Our thought was to get to PEI at the beginning of the trip for weather and availability of accommodation and "tourist" attractions.WE have 18-21 nights to enjoy this itinerary. We are definitely open to suggestions as to a better route - the goal is to see PEI, NB, NS - including Cape Breton.