Portland / Ferry Bridge Area
Most walkers arriving for the Isle of Portland Circle will be based at the main villages of Fortuneswell, Castletown and Chiswell which pretty much merge into one location and lie on the coast path just south of the mainland entrance to Portland. There are several B&B options here with good access to the beach, path and harbour area as well as a couple of more upmarket hotels further inland.
Fortuneswell is the largest of the eight villages on the Isle originally known as Fortunes' well because it was established around a small stream. Its now linked into Chiswell which sits just off the beach at the foot of the steep slopes that lead away to the northern end of Portland. Originally a fishing village, little cottages built on the back of the Chesil beach are linked by narrow lanes whose names reveal the seafaring past (Pebble Lane and Brandy Lane to name a couple). There are superb views for those staying here back over Chesil Beach and Fleet Lagoon and enough facilities for those staying overnight with several inns in the area including the famous shore side Cove House Inn with locally caught fish and seafood a regular feature. There are also a couple of good bistro options one at The Heights Hotel further into the Isle.
For those with time the Chesil Visitor Centre is close by and well worth a look and close by is The Chiswell Earthwork Sculpture made up of five low walls representing different strata of rock. Otherwise, the best evening strolls would be down to Chesil Beach, the new marina and Portland Castle or head up to the New Ground Viewing area for the superb panoramas back to the mainland.