You can do this with MonoDevelop (under Linux) and possibly with Xamarin Studio (not tested), but not with Visual Studio.
On the Raspbery Pi, run the target application as follows:
mono --debug --debugger-agent="address=192.177.88.11:10000,transport=dt_socket,server=y" \
/full/path/to/mono-application.exe
Change the IP address and path to the executable file. Note you must have debug built up, deployed with the corresponding debug files.
, → → Mono Soft Debugger. ; IP- (192.177.88.11) (10000) "". .