: Anyone ever paddle anything further afield and know how to organize
: it: Boston Harbor for example, or Newport?

I've heard good things about Boston Harbor, that would probably have to be an overnighter for most though.

Newport (in front of the mansions) is great on the right day, but can be very rough on the wrong day. If you launch from Newport (King's Beach), you need to do a real nook and cranny exploration sort of paddle or you run out primo shoreline pretty fast. Also, the Newport traffic really sucks. I like to launch from Fort Wetherill and paddle over instead. You get to paddle some Jamestown cliffs, do a quick and fun crossing, explore the beautiful Newport shoreline, see some mansions and a cool stubby lighthouse while enjoying some nice bumpy R.I. water, all in under 15 miles. I'll be happy to do one of those next summer on a nice mellow weekend. Most "intermediate" Connyakers would be ok there on the right day. A hard paddle to plan too far in advance, though.