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Re: Dinghy vs Porta Bote
If he's staying exclusively within Chesapeake Bay, motoring long distances may not be an issue.
No doubt towing a dink will slow you down a bit. For me, I've never cared because we don't generally try or need to cover long distances, nor are we ever in much of a rush to get anywhere. We're more likely to drop an anchor after a few hours of sailing, regardless of where we are, so that we can do some swimming or go explore a shoreline with the dinghy. That said, I did motor 50 miles earlier in August and was glad to not be towing a dinghy for that trip.
I guess it depends on how you plan to use it.