May depend on your definition of easy, but this is certainly a very popular paddling route -- probably ideal for intermediates and up. You can also join a guided group through a number of local outfitters if you don't want to do the trip solo. Most people put-in at Crooked River State Park just north of St. Mary's and paddle out to the Cumberland Sound through the tidal marshes. Talking of tides, this is the biggest challenge, along with wind and inclement weather. Know the tidal tables, as it could make things tough going if you're paddling against the sea currents. KayakGuide.com has a really useful trip report with more info, plus some detail about where to camp on the island: http://www.kayakguide.com/USA-Cumberland.htm