Hi. My wife is from Sri Lanka and we met in Bahamas. She went from CMB (Colombo, Sri Lanka) to DXB (Dubai) to GRU (Brazil) to PTY (Panama) to NAS (Nassau) to FPO (Grand Bahama, Bahamas). On the return trip back, she went from FPO (Grand Bahama, Bahamas) to NAS (Nassau) to PTY (Panama) to IST (Turkey) to MLE (Maldives) to CMB (Colombo, Sri Lanka).
The reason for the very long trip across many countries was that she probably wouldn't be able to get a VISA or Transit Visa and I wasn't able to fly to Sri Lanka. So we choose route that allowed Transit without Visa (had many limitations) to get married in a another country.
I used https://www.flightconnections.com to find flight routes.
I used https://www.emirates.com/us/english/before-you-fly/visa-passport-information/ to find the passport/visa information/transit without visa information.
I used https://www.passportindex.org/ to check the visa free destinations for Kenya citizens.
I did a quick check of the potential routes from flightconnections for Kenya to the Caribbean and I didn't see a possible route with "Transit without Visa". There are 2 potential ones to BGI and PAP but it requires more than the transit without visa time limit (PTY has a limit of 12 hours where you must leave the country if you're using transit without visa). PTY is a main flight hub for South America and Carribean.