I had had suspected that there was a simpler way of doing this, particularly for the encrypted web proxy, but I hadn't gotten round to actually looking into it. I spotted MyEnTunnel in some comments on a Hak5 show that had covered a similar topic so I thought I'd give it a go. So far so good.
To quote the description on the program's homepage,
"MyEnTunnel is a simple system tray application (or NT service) that establishes and maintains TCP SSH tunnels. It does this by launching Plink (PuTTY Link) in the background and then monitors the process."
It's a Windows based app and at its simplest level this gives you a GUI that allows you create a SOCKS based encrypted proxy on a specified port, as shown:
N.B. the specified port 7070 can be set to any unused port, just remember it for later.
Once the tunnel has been configured and successfully connected, the next step is to configure your browser. I use Firefox, but these settings should be fairly simple to apply to any browser.
Open your main options panel for you browser of choice (For FF Windows version go to 'Tools>Options' then select the Advanced tab. Click the 'settings' button in the connection box and you will be presented with a list of different connection settings for your browser. Now all you need to do is change your settings to reflect those in the image below (obviously changing the server, username, etc. to point at your own SSH server).
Voila! Encrypted web traffic.
There's obviously plenty more you can do with this app. If I come across anything particularly exciting during the course of playing with it, I'll either post it here or to Twitter.