Port 2376 is the docker daemon port, not the swarmkit port. Use 2377 as the port if you want to explicitly specify it, or omit it entirely in your --advertise-addr
command.
For example:
docker-machine ssh myvm1 "docker swarm leave --force"
docker-machine ssh myvm1 "docker swarm init --advertise-addr 192.168.99.101"
docker-machine ssh myvm2 "docker swarm join --token SWMTKN-1-65xbfd388nl61m4ip6qoplk0yqoze3qzq9ne9t00lmxbppt6oe-7f40hx9wn4tyu3b0nznsrqs2e 192.168.99.101"
(you’d of course end up needing to grab an actual fresh token after you re-init the cluster)