So I'm actually writing this in June 2015, roughly a full year since I've been to Nova Scotia. This was a journey I took with two of my friends after our commencement ceremony for about 10 days.  It was a long trek from Boston (who knew that Maine was such a large state?) and we ate lots of lobster along the way.  Also developed a love of oysters.

This was roughly our route (we did hit the major cities like halifax and moncton). Lots of 1-lane in either direction roads. Do keep in mind to time the trip when the Canadians aren't on school holidays (we were there roughly a week or so before the Canadians were on vacation).

Places I'd definitely go again:

Halifax

• Was worth staying in the dorms during the summer-- it was like ~$100/night for a fully equipped apartment!
• Check out the brewery, they make some great stuff! (and you get to try a lot of it, in our case, for free)
• Supermarkets are interesting-- they cook lobster while you wait, they sold tangerines from Israel, and just seemed different yet familiar all at the same time.
• The old fort is worth a look and a walk-around. The whole city has a lot of great architecture and history.  This is where most of the British supporters moved to when the British lost the Revolutionary War.

Pictou

• Wish I spent more time here-- we drove specifically for the Grohmann knife factory which requires FOUR people to take a tour. Will have to come back for that. Ended up buying lots of great kitchen knives from them at discount prices! (though no warranty)

Sydney

• Kind of a weird fishing town that wasn't quite touristy and wasn't terribly interesting. However, coal mining is a big deal up here, and you can actually go on tours of real mines. As it turned out the "real" mine was closed and the smaller miner's museum was open (our tour guide who had actually grown up in the town with the smaller miner's museum and had actually worked in that mine before told us that his museum was the real deal, and most of it is flooded since it was below the water table). 

Cape Breton

• The Cabot Trail is very scenic and well worth the drive. We found it to be much prettier going counterclockwise rather than clockwise (plus you could pull over easily to stare out over the ocean).
• Overall a great place for hiking. We stayed at a cabin at Igonish. Do check out the Keltic Lodge in Igonish (it's got quite a nice hike for a decent view) and the food is good. Plus they have live music!
• There are great trailheads you can pull off and visit. It wasn't terribly warm yet (still snow in some places in late May) so we didn't do a whole lot of hiking. But we did see a moose!
• Do go to Cheticamp and eat seafood there. They had steamed crab, lobster, and raw oysters. Yum.
• Just south of Inverness is the Glenora Inn and Distillery. Some of the smoothest scotch I've ever had (go for the 15 year) and some of the most amazing food I've had ever. Highly recommend eating here (lunch and dessert are excellent) and they too have live music. The distillery tour is also like $7 CAD and is totally worth it! (You get a taste at the end.)

Bay of Fundy

• Hopewell Rocks are really strange. Almost like the faces on Easter Island, just naturally sculpted.
• Try a lobster. They do taste different. Just make sure they're not overcooked.
• Rockhounding is a big deal here. 

Helpful Tips:

• Oysters are great but they try not to serve them to you within two weeks of snowmelt (you'd get sick since oysters are filter feeders and the runoff has human waste).
• Follow random signs to go places. We read touristy brochures and drove down skinny streets to end up at a fruit-winery near the Hopewell Rocks. 
• If you want to go to the beach, make sure you look at the tides tables. ESPECIALLY in the Bay of Fundy, which has something like a 12 foot difference between low and high tides.
• Unless you're super hungry, think twice about eating any poutin (though it is really good).

Places to go to next time:

• Yarmouth.
• Hiking in the Bay of Fundy.
• Taking the ferry to Newfoundland
• Going to Prince Edward Island (PEI)

Truthfully I've been here mostly for the food, though I've enjoyed walking around this newly remodeled hipster-like port. They've got a lot of local artists and some great stores showcasing the art/pieces you can use for daily use. Lots of unique things here, though I really have to see more of the place and am giving a fairly skewed view of the 5-block area I've been to!

Food: Grab some Omakase at Miyake, located at 468 Fore St.