Isle of Wight Loop, heading counter-clockwise from East Cowes. The route begins with the novelty of the chain ferry / floating bridge, which runs all day and is just 50p for a foot passenger as of July 2024. The main event though is the climb up to St Boniface Down out of Ventnor, #123 of Simon Warren's Greatest Climbs and rated as a 5/10. However, this route extends that by starting the climb from the Esplanade to get in the alpine style zig-zags.

At just roughly 100km, this route should be do-able without stops, but there are good options to re-supply or grab a coffee on the route at Yarmouth (22km / 14mi), Ventnor (59km / 37mi), Shanklin (67km / 42mi), Sandown (72km / 45mi), and plenty more a little way off the route.

The routing is mostly by road, some of which is quite busy, in particular the section from Freshwater to Chale (Eastern to Southern tip of the island). This can be avoided if desired by taking one of the turnings in land and then taking a quieter parallel road. Here is a slightly modified route that avoids that and another section of busy road on the way into Yarmouth.

The route includes a short section on bridleway to get down to Shanklin from St Boniface Down due to a landslip in Winter 2023 making the road from Ventnor to Shanklin unpassable to even foot traffic. For those wanting to stick to paved surfaces, this further modified version of the route is worth considering. For those wanting an offroad adventure, have a look at this route which is approximately 50% off road (on bridleways).

All of the above mentioned routes can be viewed on a single map, here.

Getting There

Red Funnel operates from Southampton to East Cowes on every hour from 0500 onwards, with the return ferry also departing every half hour until 2030 (with the last ferry at 2330); travel time is approximately 1 hour. Cost for a foot passenger return (with bike) in July 2024 was £22. The ferry terminal is just 1 mile from Southampton Train Station, for which there a 3 direct trains per hour from London Waterloo, taking approximately 1hr 15mins.

Nominal Timeline for Ride Day

0805 - Train from London Waterloo

0922 - Arrive in Southampton Central

1000 - Ferry to East Cowes

1100 - Start Riding

1700 - Return to East Cowes

1730 - Ferry to Southampton

1900 - Train to London Waterloo

2020 - Arrive in London Waterloo

If doing the gravel version of the route, expect to take at least 1hr longer; it is probably sensible to bring the start time forward by an hour.