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San Juan del Norte is a historic village in the south east corner of Nicaragua. Tortuguero Costa Rica is also in this area of the Caribbean. In 2008 we used local scheduled panga services to travel from Tortuguero to SJN and the back up the Rio San Juan and Rio Sarapiqui to Puerto Viejo de Sarapiqui , Costa Rica. All of this was done legally and safely. See my forum post dated Jan 25/13
Travel by rented vehicle from north to south on Highway 21, Playa Hermosa to Montesuma and across to Puntarenis. The roads are paved except for sections between Naranjo and Paquera and the last 7 kms to Montezuma. Travel by day is recommended. The dirt road sections are at points steep with sharp curves, but can be travelled safely at reduced speed without the need of a 4x4 for most of the year. All roads except the Pan Am, the toll roads, the Pacific Coast Highway and most of #245 are narrow and one lane bridges are frequent. Speed averages between 50 and 70 kms per hour. See my Dec. 2012 forum posts for details.
In December 2012 we travelled by rented vehicle from Sierpe overland to Drake Bay. The trip took under 3 hours via the back road to Rincon, a short jaunt on Highway 245 and then a 30 kms trip across to Drake Bay on another dirt road. The trip affoded excellent views of the OSA Pensinsula, experience on steep and winding hardrock dirt roads, river fording and a chance to see and be in a place that many never get to. The trip was safe, though an SUV is recommended for fording, suspension and gearing as some of the roads are rough and very steep. We used the 4x4 only once at the deepest river crossing (12") and it was probably not required for traction ... but better safe than sorry.