Just returned from a wonderful week on the Dawn from Boston to Bermuda. We traveled as a group of 7 (ranged in age from mid-30's to early 50's). Two of us had sailed the Dawn twice before to Bermuda, 1 had sailed one other NCL cruise on the Getaway, 1 hadn't cruised for 25 years, another used to work on cruise ships (HAL) and 2 were newbies to cruising - so we had a diverse group from Eastern Canada!
(1) PORT/HOTEL: We stayed at the Holiday Inn Express in Saugus, MA. which has a lovely covered parking garage to keep your car while you're away and the hotel is lovely with a good breakfast. It is also very easy to get to if you're coming from the north. It is a way's from the cruise port but they have a free shuttle to the airport so we took the shuttle to the airport and then 2 cabs from there to the port (cab from the airport about $25-35). It was smooth both leaving and arriving back in Bermuda.
(2) SHIP: I think it is key to remember that the Dawn was built in 2002 and has been refurbished (and will be again in early 2016). If you're desire for cruising is the new flashy multi-waterslide, ropes courses, wave pools, multiple pools, ice skating rinks, climbing walls, etc. etc. etc. then I'll tell you right now you'll be disappointed. That being said the ship is still in great shape. The pool is a bit small, but I'm not a big pool person so it didn't trouble me. A couple of others in our group were disappointed. There are many restaurants, many bars, many chairs (yes, they do fill up but there are always people getting up and going inside - we never had a problem finding a few together).