RE:Bay side or South Side
Yep - there are BIG bass in shallow flats on the bayside right now... <b>BUT</b>
Since you're night fishing with no moon my recommendation is "don't go to Brewster flats". We like having you around. Night fishing on the flats can be deadly, especially if this is your first time across the trenches old man winter has sculpted out to the channel edge this year - and with no moon, radical temp variation and potential pea soup fog, first timers along, tempting incoming tide just after dawn when the fish will be going nuts and making you want to stay out there slaying them as they come over the flats... I'd wait till the weekend for a 4am start fishing through the drop on that -1.8 low! Big minus, extra time out there.
Barnstable Harbor would be smarter because you don't really go out on a limb in most places. The rocks at Sesuit would be a great place to introduce your friend to stripers... work from left to right and be working clousers with deep slow twitches in the hole to the left of the jetty from the last bar at low tide / dawn, I think it would work. With the cold water temps they are probably in the estuary and will be dropping back with a vengeance during the ebb tide, to the right of the jetty from the tight boat channel down the flat to the base of the jetty, sand eel / silverside patterns on a sinking line when the current is running. If it were the start of the outgoing I'd recommend Chapin, but with this tide...
You might find some giant fish backing out of Dowses, laying in the 20 hole right in front of the lot as low tide approaches.
Wianno at dawn, outgoing - you know the drill from when we were there last, no pogies though - the forage is small / or large herring.
Hardings - the death march, but sweep the beach (casting / stepping) to the outlet of Stage. Not the best place at dead low but fish deep and thorough around every current ridge and it's likely that you'll find big stuff.
Shoals around Herring river have been giving up a lot of keepers but during off-hour high tides. You can wade out there closer to the edges at low but with no moon... not my first choice. Work over to the halogens (west) and you might find a blitz of epic proportions under the lights! Of course by that time theuy are probably turned off. Not a good choice overall for this venture.
Bass River... with the cold water the key is to go up into the warmer creeks. For moderate action, lots of rats with a few in the keeper class you should consider parking at the creek near the circle, walking into the estuary just past the boat docks and fishing that whole backwater as far as you can as the tide recedes. This has been much better at night after a daytime warm up but there is lots of bait and some real chunky fish in there due to the cold outside water temps. You may find some action on the drop fishing on the shoals that expose at the base of the big west dennis jetty, or if you're lucky just sweep the beach (better with partial moon) until you find some fish. Big fish have been in the area recently, herring are the preferred forage.
Parkers - my suspicion is that there are big fish up inside the peat banks and deep inlets between rte 28 and the mouth. At low, sometimes you'll see fish feeding down by the lifeguard station just off that little mini-jetty, but for the most part it's a high tide location out on the beach. If you hit it go up inside.
Chatham - A great fishery for night time is the beach at Chatham light. I'd walk north and start at the rockpile, then work it down to the bar which has really changed over the winter. It almost appears as if you could walk out to the last bouy as the tide drops. You can park free of hassle until 9am + grace period, so you'd be covered. The current runs hard, use sinking lines and flies that can get deep. Pay special attention to the deep trench just before the boat channel turns toward the spit. The fish often run along the edge just a short cast away.
I envy you, but not for choices!