Joined to the mainland near Weymouth by the shingle of Chesil Beach, Portland is the southernmost point of the Jurassic Coast and its coastal path can easily deliver a full day of walking (between 10 to 14 miles depending on whether you tackle Chesil).
If arriving by car, drive up through Fortuneswell to the car park at the top of the hill on the way to the island’s prison The Verne. Don't be deterred! By walking towards the prison, you will soon hit the coast. What you can see of the prison is architecturally interesting, too.
Walking clockwise round the island, the first stretch of coast will see you walking beside sheer cliff edges (a mecca for rock climbers and abseilers). The gravel path winds its way towards the red- and white-striped Portland Bill Lighthouse, which is surrounded by rows of colourful cliffside beach huts (that are sold for eye-watering prices).
From here, the path opens up and snakes along the grass-topped cliffs, passing Mutton Cove (named after the famous breed of Portland sheep and home to many shipwrecks) and Blacknor Fort. After a few wind-blown sections, you will be grateful of the descent into Chiswell, a tiny fishing village with a striking sea wall, allowing you to avoid the Chesil Beach shingle (which is hard going after the undulating coast path).
At this point, you can either walk back towards the mainland to extend the walk, or make your way through the marina and build up strength for the steep climb through Fortuneswell to the car park. There are a few routes, but there is an interesting old tram track, which will distract you from your aching legs.