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In your case, given that you will be sailing in the Chesapeake, I would be focussing on a dinghy that could be easily towed behind, or occasionally stored on the foredeck for longer trips. Inflatables are okay for this, but hardshell dinghies usually do better for towing.
Inflating and deflating a dinghy every time you arrive at a destination can be a real nuisance, especially when you are daysailing/overnighting (it's not as big a deal if you are making longer passages and then staying put for days or weeks at a stretch). I know very few inflatable owners on the Chesapeake that are constantly inflating/deflating. Most are storing the dinghy in davits or on the foredeck.
Others may feel differently, but we have never needed an outboard in our years of cruising the Chesapeake. Rowing and sailing has always served well enough. But we use a hardshell dinghy, which tows and rows easily and sets up quickly for sailing. Without the weight of an outboard and gas, you could easily manage with an 8' pram or dinghy.
Good luck! You'll get lots of differing opinions here!
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT
Last edited by JohnRPollard; 01-07-2009 at 11:43 AM.