As requested by Lieste - some shots of Portland and Weymouth in X-Plane 10 using Simheaven's ZL17 photoscenery and World2XPlane object placement.
I think the Simheaven photoscenery is based on Google Earth imagery. The W2XP stuff is still in beta, but basically it uses OpenStreetMap data and runs it through an algorithm to place buildings, forests, roads, etc in the correct location as indicated by the OSM data. It's not perfect and very reliant on the quality and quantity of OSM data, but it can make more accurate results than the old fashioned "autogen" object placement in MSFS.
I'm very familiar with the area myself, having spent a lot of time on ships operating out of Portland. Last time I was there was during the 2012 Olympics when my ship was operating as part of the security operation.
Click on the pics to open them in Imgur at full size for a better look.
Looking back down Chesil Beach towards Portland. Not a bad representation at all. You can see the coastlines are rather crudely cut out, but considering this guy has covered pretty much all of Europe and it's freeware I'm not going to complain too loudly. I'm not so sure about the trees on Chesil Beach though.
Looking across Weymouth and the surrounding area.
The marina is overdone, that's a result of the object library using jetties that are too big. You'll also notice most of the buildings in Weymouth's shopping precinct are missing - again likely a result of the data being missing in OSM.
Not a bad representation of the harbour. They've even got the two old WW2 Mulberry harbour sections in Castletown. They've also got a pretty good representation of Q-Pier, the Outer Coaling Pier and Deep Water Berth. I'm not so sure about the trees that are on the sea wall though....
Some of the buildings on the Verne. They've managed to get pretty good representations of Castletown, Fortuneswell, Easton, Weston and Southwell.
The lighthouse on Portland Bill is there as well. Again note the crudely cut out coastline.
Finally the whole area at night.
Is it all perfect? Nope. Is it better than the default? Yes miles better. Considering the scenery is all available for free, and the only real caveat is going to be hard drive space then this really is pretty good.
Just remember it's Portland and you shouldn't mention the rabbits!