Across the Sound, to Shelter Island? Have you been through Plum Gut? Here is a video of some sea kayakers out playing on a calm day: https://youtu.be/tv8Tk3LWTHo - The tidal current runs 2kts+ let alone the waves when the winds blow (usually). Of course, you could paddle to New London, then take your canoe on the ferry to Orient Point... that would make for a cool photo :) In all honesty, if Long Island Sound itself doesn't scare you, there is a spot in Southold where you could portage over to Gardiners Bay (coordinates: 41.1354477,-72.3302537).

Easy portage, about 200 meters. Take out on the right side, miss it and you will be sorry in a canoe.

I scouted (and portaged some) portages from cannan to bellows falls, most are only partially wheelable. Lyman falls, you prob will run this, make sure your far to the left, almost on shore. if you want to stay at the state park site cross the river back to vt side immediately after you're through the dam, if water is high and fast(like it was for me) you may have trouble pulling in, jumping out and pulling it in is an easy option here. there were several sections of rapids(in early june)in the northern river that I was able to go over MOST of the rocks,but the water will prob be much lower for you in sept so be prepared to get wet and line it, and hit rocks. North Umberland Dam- some ppl run this too(best to scout it from the bridge)I choose to portage as current was kinda quick in june, I had to jump out quick and pull it up onto the bank, there were supposed to be about 6-7 wooden steps but they hadn't been put in place for the season yet(june 2)but not too difficult pulling my 100lb(est)kayak up bank unfortunately there are then about 15 or so steeper rough stone stairs(I lightened my load a bit and really worked to get the kayak up)then carted across the rd, you then come to wide,shallow,curving wooden steps(about 20)I tried to wheel down them(looked possible) but it was too much strain on my cart so i de-carted and slid it to the water(easy), you would have an easier time as you are 2. at the water the silt was crotch deep, go to the right to a small rocky outcrop and get in there. GILMAN DAM- take-out on left, easily wheelable right from waters edge, take right at grassy jct also was a garbage can here(eliminate trash), easily wheelable to within 50' of river then de-cart and carry(or drag) over fallen logs and rocks, current was kinda fast so I did kind of a seal launch, but again should be easier as you are 2(don't forget to check for ticks), MOORE DAM PORTAGE- first 15' i had to drag over small rocks and a few smaller logs(not too hard)once on the grass i could have wheeled it but choose to just drag it(was bit heavy pulling it up the hill, but quicker than getting cart out) got over top and running, dragged it downhill(could've rode it down on the steeper section, WEEEEE!!!) downhill momentum ran out and dragged it to where dock was, I choose not to use the dock and slid it down the bank just to the left of the dock(easy). Comerford dam- portapotties at beach landing,wheeelable to where the road turns left then I would drag on grass to stairs(you might be able to wheel as you are 2)(grass slippery when wet)just before stairs is a 10' long rocky area(de-cart and lift over)...you are now at the top of about 80 stairs(yippee), it is possible to gently slide a boat down and re-cart at bottom, bottom is wheelable to within 10' of water, then carry over rocks, I've heard of ppl going around stairs by portaging an extra mile but I didn't look into this as I was in a hurry. Mcindoe Falls Dam- this one is not easy. tak-out to a flight of about 25 wooden stairs right down to the water(current was fast when i was here making it difficult, would have to jump out super quick(in deep silt) get up on stairs,grab heavy boats handle and pull up onto hill, unload boat(on steep hill)and carry gear up stairs, pull boat up gravel on side of stairs, from top of stairs to the top of 4-5 stairs at downriver side is easily wheelable and the 4-5 stairs(and rocks and logs)are somewhat easy to drag over to the water. again you might have it easier being 2 and a canoe. Rygate DAM- take-out is easy on rocky outcrop, campsite is just inside trees(I'd just drag or carry boat into it if staying here and cart up after set up)was 20 or so downed trees here in trail when i was here(get around them on the right), but hear they've been removed. easily wheelable(if no trees) from take-out to within 20' of water at put-in, then easy drag(or carry) to water. Be mindful of your balance going through the narrows just north of Wells river vt. WILDER DAM-take out is easiest just past where trees end on left, easily wheelable till you get to about 15 rough rock stairs, easy enough to drag down, then another drag(carry) of about 100'+/- over semirough ground to the water(cart may be possible here, but risk damaging it),was a dead deer just to left of stair bottom. sumners falls-dont run this, take out river right, put-in is good. bellows falls dam- easily wheelabe(just a bit long) I would portage on the nh side(1.5mi), its a bit longer but I know it better and there's a sm. grocery store along the way. if any other questions just message me.