In reply to tdryden:
For trad forget Portland and the outliers, Swanage is the place to go. A car would be useful but not necessary, there is a frequent bus service, Breezer 40, from Poole that passes nearmost of the parking spots for climbing asking the coast, for the Eastern end of the cliffs the 5 from Swanage takes you to Durlston and the approach to the Boulder Ruckle, Swansea premier crag.
For partners try the Dorset climbers page on fb
For your first visit consider scaling back your ambition to 5.8/5.9, trad at Swanage is pretty daunting! It's steep, committing, not totally solid, above the sea, and totally magnificent.
Post edited at 08:46