So you are actually planning 5 days sailing with 4 nights stopover in between. That's about 150 miles with all the ins and outs around islands and points. That sounds like a great plan and easily accomplished! I had a dinghy on board for our trip from Cape Cod to Barnegat Light, NJ ... we never used it. I left it in it's carrying case the entire time (5 stop-over nights), strapped to the deck in front of the mast. Between the tenders in the mooring fields and a marina, there was no need. We did anchor one evening at Sandy Hook, but had no desire to go ashore. But if you worry about pumping it up, there is no need to worry. You don't need an electric pump. It should have a foot pump with it and that is going to be fine. When John says 30 minutes to pump it up, that includes all the layout and fussing around with the valves. The actual pumping is easy with a foot pump and takes no more than a few minutes - just make sure it has the correct fitting for the valves. Now that I know the routine, I can pump my 9' inflatable (2 tubes, a floor, and a keel) in about 15 minutes and half that time is fussing with the valves and the seat. I wouldn't tow it unless you have very calm days and are motoring. I suspect you won't need it at all.