When I connect my DriveSmart 55 to my MacBook the data transfer option is greyed out ?

How are you trying to do that?

I'd assumed that, if you want help we need some detail.

Sure what detail do you need ?

Exactly how you're trying to transfer data, and what data it is.

It's 11 way points and 4 routes all in BaseCamp that I want to transfer. When I connect the DriveSmart to my MacBook Basecamp does not see the DriveSmart GPS. 

If BaseCamp does not see the device it's quite obvious it cannot send anything to it...

I suspect the Drivesmart is using MTP to connect to your MacBook. There are some restrictions regarding MTP and MacOS, the device will not show up in Finder and only one program can connect to the device at a time.
Garmin Express starts up automatically by default and will block access for other programs. Open settings of Express and uncheck both options. Close Express using Cmd-Q, and try again with BaseCamp.

Thank you, thank you it works now. Transfer was 100%