We were on the Sky last Fall for 20 days. We did roundtrip from Baltimore. It was easy to embark and disembark in Baltimore. We had perfect weather on the way to Quebec, not so much on the way back. We made the most of it and enjoyed the cruise very much.
The sports bar isn't a 24 hour restaurant, unfortunately. On sea days, one of the main dining rooms will be open for breakfast and lunch. Cagney's is great, LaCucina was ok but LeBistro was amazing. If you like pork chops, try one. It was the size of a small roast.
We also took the hop-on, hop-off bus in Boston. We booked through Viator which saved a few dollars. We cruised over Labor Day, so we got to see the swan boats (it was the last day of the season).
The Sky is really small but we enjoy her. The cabins are compact so storage is tricky. We use packing cubes and left our folded clothing in the cubes and stacked them on the safe.
I think the Sky has Starlink now and the cabins have USB ports in the lights by the beds. You'll find just one US electrical outlet at the vanity/desk. This area is very tight. If you're planning on working, I suggest you find another area on the ship so you can spread out a bit.
If you have any questions about the Sky, I may be able to help you. Enjoy your cruise!