Actually, I had wanted to plan a ride from FL to CA many years ago. However, my MB buddy moved to TN. We would've had our wives follow us on a rental truck.
but not on island rides.
Ed and I rode most of Oahu in sections, from East side Sandy Beach to the North shore side of Kaena Point Park. We PUSHED & CARRIED our bikes thru deep sand thru the entire park, to get from the North shore to West side Waianae town. There are no roads connecting the North shore to the West side of the island. Since the road to Waianae is washed away, we CARRIED our bikes along the cliff(!!) to get to the West side. Reaching Yokohama Bay, we rode thru Waianae towards Kapolei. My twin-engine Mitsubishis/90-lb. cruiser never missed a beat.
However, my rear tire blew out in Kapolei, and the 50-mile ride was over. Ed's China Girl/ Trek bike performed well, except for a couple chain jumps from his shift kit.
The toughest hills were from Sandy Beach to Hanauma Bay and from Waikele to Mililani. Ed's bike struggled, even with shift kit. My twin-engined friction driven bike had no problem, due to the doubled torque output.