So to recap - really did enjoy my foray out here. Folks are generally quite friendly, and definitely a bit provincial (they were quite surprised to chat with someone from NYC).

-Stayed at the Holmer Grand: pretty meh as a hotel, but centrally located. Parked for free on the street after 8 PM.
-Dinner @ Claddagh's - excellent choice. Fantastic oysters and the entree (glazed pork belly and scallops) was excellent
-Hit up Darnley for sunset. Definitely a bit of the drive, but I got lucky - first clear day they had in weeks - and was beautiful. Because dusk is relatively long, it wasn't completely dark until I was most of the way back to Charlottetown
-Stopped at Upstreet Craft Brewery for some beers - average at best. Wasn't blown away by any of the beer I had in PEI, but there is a local scene, so at least you aren't stuck drinking Molson
-Brunch at Water Price Corner Shop - excellent oysters and chowder; the lobster roll was worse than I've had in New England

Transportation thoughts:
-Flying AC Rouge is a tight fit. Now I understand why so many folks despise them
-YYG is a very small yet pleasant airport. Extremely easy to get in and get out of
-I didn't come across many potholes that I felt would have absolutely wrecked my tires, but there was definitely some dodging driving happening. I got lucky when Hertz upgraded me to an SUV for free...definitely takes some of the mind off of watching out for gaps in the asphalt.