I'm in the process of creating the "Ultimate Sailing Cooler". The motivation for this is just to have the most technologically advanced cooler that ever existed. It will be used mostly for sailing small dingy boats.
Phase 1: Install Stereo Equipment and Electronics Compartment (In Progress)
I completed this over the weekend. Bought some cheap marine speakers and a DIY Class T amp board online. Hooked up to a 12v battery. The electronics are partitioned off from the rest of the cooler by a modified cutting board. Everything is sealed with silicone. All connections are just soldered and heat shrinked for the moment. Later, as it gets more finalized I will probably add connectors. Sounds great to far, but nothing to too technologically advanced. Input is from a small MP3 player.
Phase 2: Heads Up Display, GPS, Temp Monitor (Parts Ordered)
Arduino will run the whole thing. I have never done Arduino work before, so I am excited to get my hands dirty. Inputs will be a couple temp sensors and a GPS module. Outputs are to a 20x4 character LCD that will be mounted on top of the cooler. GPS data will also be logged to an SD card so I can overlay all my sailing this summer onto google earth. LCD display will be heading, speed (knots), outside temp, cooler temp, battery life, and..... anything else I can think of. Maybe roll angle if I was adventurous and installed an accelerometer.
Phase 3: Solar Charging (Planned)
Adding a 10 W solar panel to the top. There isn't really a need for this, so of course it is a requirement for this cooler. It will also up the visible 'cool' factor
Phase 4: Connectivity (Out there)
I will probably add bluetooth, wifi, or cellular connectivity. Maybe I will set up a tether to my phone so the cooler becomes a wifi hotspot. I need to come up with some more ideas here.
Phase 5: Mobility (WAY out there)
If there is anyway I could make this move on its own, I might try. It will float, so I could add a propeller and a rudder system. Maybe some wheels and steering.