UDP maximum segment size

For a simple windows based application you can try Logmein Hamachi.

For a more advanced solution for NAT to NAT connection udp/tcp look at pwnat.

UDP datagrams have little to do with the MTU size you can make them as big as you like up to the 64K is maximum mentioned above. You can even send one of them in an entire packet as long as you are using jumbo frames with a size larger the large datagram.

However jumbo frames have to be supported by all the equipment the frame will pass over and this a problem. For practical purposes Ethernet frames are the most common tranport size, the MTU for these is circa 1500 bytes, I will say 1500 going forward, but it isn't always. When you create a UDP datagram larger than the underlying MTU (which as indicated is most often be ethernet) then it will be quietly be broken up into a number of 1500 byte frames. If you tcpdump this traffic you will see a number of packets broken at MTU boundary which will have the more fragments flag set along with a fragment number. The first packet will have a fragment number of 0 and the more fragments set and the last one will have a non-zero fragment number and more fragments not set.

So why care? The implementation detail actually matters. Fragmentation can hurt performance in the network not a big issue anymore but one to be aware of. If a huge datagram size it used then should any fragment be lost the whole datagrams will need to be resent. Equally at high volumes and today these are perfectly achievable volumes then mis-association of frames at reassembly is possible. There can also be problems getting fragmented UDP packets to traverse enterprise firewall configurations where load balancers spread the packets out, if one fragment is on one firewall and the other on a different one then the traffic will get dropped as incomplete.

So don't create UDP datagrams bigger than the MTU size fragmentation unless you have to and if you have to specify that the infrastructure being communicated between is close (same subnet close) at which point jumbo frames would likely be a good option.