The latest version of PlayUp allows you to export entire levels to CryENGINE 2. When you export, a .GRP file is created and placed into your level folder. This file contains information on the placement of the TOP LEVEL components/groups in your SketchUp file. Any nested components/groups will be merged into the the same mesh as the top level component/group.
You'll notice a new field in your PlayUp Preferences window under the CryENGINE 2 tab for "Starting Coordinates". Here, you can specify the coordinate in CryENGINE that you would like to line up with SketchUp's 0,0,0 coordinates. Since CryENGINE places the 0,0,0 coordinate in the corner of the world, this setting allows you to specify a more practical starting location.
In Sandbox 2, go to Modify > Load Objects and select the .GRP file. Please note that CryENGINE has a limit to the size a mesh can be. If a file is missing, try to break it up into separate top level components/groups to reduce the amount of faces/vertices in a single mesh.