A trip from Lisbon to Madeira taking the scenic route though the airports of Santa Maria, Joao Paulo II, Lajes, Graciosa, São Jorge, Pico, Horta, Corvo, Flores and finally Madeira.

I suggest starting it early in the day, before the sun comes up, there's a 3h flight through the Atlantic that can be done in the dark, reaching the islands around 5-6am is simply perfect if you are lucky to get a good weather.

Your First stop will be the Island of São Miguel, a great spot to refuel, stretch your legs and do a bathroom break, from there we start island hopping with flights no longer than 30min, with most being only around 5-10min. So no need to worry about fuel, you can always find a low traffic runway to land, be aware though that some are rather small and with no lights.

Because of that I recommend a plane with short take off and landing distance capabilities as well as autopilot for the long stretches of the path, like the TBM 930.

After we visit the Island of Flores, we'll start our travel to Madeira, it is a long way but we have the Island of São Miguel as our midpoint in case you need to refuel or rest.