RVr2,
Karin and I in our R27, with friends in an R29, made the Okeechobee Waterway crossing and return from Ft. Myers Beach to Stuart then down to North Palm Beach in late April, 2013.
Before crossing, you might consider stopping off at Estero Island in Ft. Myers Beach, a fun place with lots of broad white sand beaches. From one of these marinas you can explore the many islands in this area or even venture south to Naples or Marco Island. Some marinas:
http://pinkshell.com/fort-myers-beach-marina/ floating docks & walk to beach
http://www.saltysamsmarina.com/ floating docks
http://www.mossmarine.com/mainmenu.html fixed docks & walk to beach
http://matanzas.com/dockage/ mooring field
When heading up the Caloosahatchee River, you might stop off at the Ft. Myers City Docks (Fort Myers Yacht Basin):
http://www.cityftmyers.com/Yacht-Basin.aspx
Just so you are aware, another favorite stop along the Waterway is now permanently closed:
Rialto Harbor Docks (about 15 miles east of Fort Myers Yacht Basin)
Next stop heading east might be La Belle City Dock, but there is dockage for only about 6 boats where you need to dock stern-in with an anchor out to keep the bow from swinging:
http://www.marinalife.com/reservations/ ... a-belle-fl
Just beyond La Belle City Dock is:
http://portlabellemarina.com/ Nice protected marina in an oxbow off the river.
And hidden on the north side of the river a few miles farther east in an oxbow is:
http://www.riverforestyc.com/ A full service yachting storage and service center that also has tie-ups in their yacht basin for over-nighting. We truly enjoyed the solitude and beauty of our stay there.
Next stop is at Lake Okeechobee, just before crossing:
http://www.rolandmartinmarina.com/ a fun marina, home to Little Man the best dockmaster in the world.
After crossing Lake Okeechobee, you might stop at Indiantown or just continue on to Stuart:
http://www.indiantownmarina.com/
In Stuart, we truly enjoyed our stay at:
http://www.sunsetbaymarinaandanchorage.com/ - a short walk to the old downtown and shops.