Isle of Wight Clockwise 116 km

This cycling trip is a nice way to discover the Isle of Wight in one day. It takes you clockwise around the island, following parts of the official Round the Island cycling route (see a.o. http://www.visitisleofwight.co.uk/bicycle-island/taste-round-the-island-route). It is completely paved, apart from a 2.6 km stretch of gravel cycling path along the river Yar (see waypoint for more information). The route will give you beautiful coastal views of chalk cliffs, beaches, mud flats, bays, sheltered harbours, tidal rivers, and estuaries, scenic coastal towns, quiet countryside and hills.
The route starts where the catamaran from Portsmouth docks on the Ryde Pier (see waypoint). This catamaran sails from the end of the train platform at the station in Portsmouth (http://www.wightlink.co.uk/). If you arrive by car to Portsmouth, you can also park close by in the Gunwharf Quay car park. Note that you actually have to go onto the rail platform to get to the boat. After disembarking, you ride down the Pier and then turn left towards Seaview. After a bit more than 1 km, you follow a cycling path hugging the shore of the Solent (see waypoint). From Seaview you ride towards and around Bembridge Harbour, a natural harbor with boats falling dry at low-tide. From there you ride towards Sandown and then Shanklin, both seaside resorts on the Sandown bay. The roads here are a bit busier until you leave Shanklin to climb Cowleaze Hill to about 160 meters above sea level. You then descend to Ventnor where you choose the Undercliff Drive to St. Lawrence. Unfortunately, the Undercliff Drive towards Niton is closed because of landslides (see waypoint), and you have to make a steep climb to get to Niton via Whitwell. The road climbs a bit further to 180 meters, and then you have a magnificent view all the way to the chalk cliffs at the western end of the island. You can then follow the Military Road all the way to Freshwater, but I followed some of the quieter stretches inland, as also indicated by the round-the-island signs. South of Brighstone you join the Military Road again, and the views of the chalk cliffs on Compton Bay and Freshwater Bay and Tennyson Down become better and better the closer you get to Freshwater (see the waypoint ‘Military Road’). From Freshwater, you go towards Alum Bay. This is a dead end route, but from here you can climb a paved road not accessible for cars to several viewpoints (see waypoint) of the Needles (sharp chalk needle-like cliffs at the west end of the island). You can also visit National Trust landmarks (Old and New Battery) there (see waypoint). After having visited these landmarks you cycle back and then go to Totland, and then to the river Yar in Freshwater. There is a cycling path here besides the tidal estuary. Unfortunately for racing bikes, it is only semi-paved with gravel (see waypoint). I followed it anyway (see waypoint for alternative route if you do not like the gravel) to Yarmouth where you ride through the center (one-way traffic) and then go east. The route goes a bit inland before it turns north and passes the Newton river, another tidal estuary, and then continues inland to Cowes, where the trail follows the Solent along the esplanade. Here you have nice views of the Solent, and the mainland. Near the center of Cowes the trail follows some shopping streets for a few 100 meters (pedestrian zones). You then cycle on to the ‘Floating Bridge’, a ferry towards East Cowes (see waypoint). You take the ferry to cross the Medina River, and then climb out of town before taking a quieter route towards Wootton Bridge. After crossing another tidal river (Wootton Creek) you turn right for the last stretch back to Ryde. In Ryde, you cycle down to the coast and then go back to the ferry dock at the end of the wooden Pier.
Some of the roads were busy, especially the main roads between Cowes and Ryde, and in Sandown and Shanklin, but much of the roads were reasonably quiet or even deserted in some places. On the Military Road on the south side of the island, I guess you could catch a lot of wind: if the wind is strong and blowing from the west, you may consider cycling the track counter-clockwise. You will not have problems finding something to eat or drink: there are lots of opportunities in e.g. Ryde, Cowes, Freshwater, Alum Bay, Shanklin, Yarmouth etc.
Route Ryde/ Seaview/ St. Helens/ Bembridge/ Sandown/ Shanklin/ Ventnor/ St. Lawrence/ Whitwell/ Niton/ Yafford/ Brighstone/ Freshwater Bay/ Alum Bay/ Totland/ Freshwater/ Yarmouth/ Thorley/ Wellow/ Shalfleet/ Newtown/ Porchfield/ Cowes/ East Cowes/ Wootton Bridge/ Fishbourne/ Ryde.