Silenus, the default speed of the Galileo serial console is 115200. Have you tried connecting at 115200 baud?
Also, I would double check that you don't have the RX and TX lines switched.
If you are worried about Parallels interfering with the functionality of the USB adaptor (my adaptor works fine in parallels), you an always try connecting from your Mac.
To connect to the Galileo's serial console from OSX, type the following command (without quotes)
'screen /dev/cu.usbxxxxxxxxxx 115200' (where /dev/cu.usbxxxxxxxxxx is the name of your serial device)
you can see a list of usb serial devices attached to you mac by running this command: ls /dev/|grep cu.usb
Okay so i hooked up the connection to an oscilloscope finally. I have a usb to rs232 adapter plugged into a macbook pro (im guessing a usb3.0 port). I hooked up the oscilloscope to the output pins of the usb to rs232 adapter. When I use a program like coolterm and setup a serial connection through usbserial-A9MXH3J7 and start pressing random keys, I can see the TX light on the software light up, but absolutely nothing is coming through the actual pins of the rs232 side of the adapter. I installed the FTDI drivers for the adapter and it seemed to recognise it fine. I'm not sure what brand the adapter is, looks like a bit of a no-brand type.