Hi Wheelie:

A very useful and thought-provoking post, thank you for taking the time to share your ideas.

But... not all of us are the same, so, with my tongue firmly in my cheek, may I offer an alternative perspective:

Sleep In:
Remember, you bought that motorcycle for recreational use, not to get you to the office every day. A vacation (or retirement, as the case may be) is a time to relax and unwind. So, find out what the check-out time at your hotel is, and ask for a wake-up call an hour before check-out time. There's nothing better than having a good long sleep before a day of riding.

Pick a DIRECTION, not a destination:
I learned long ago to not pick a specific destination, but instead, to simply pick a direction to go. For example, if I start in Zurich, I might decide to go south-west. I'll aim the motorcycle more or less at the south end of Portugal, but it's not essential that I eventually get there. After a few weeks, maybe I might get to the end of the road, then again, maybe I won't.

Don't fall into the trap of telling yourself "I need to get to this specific city by the end of the day". Just get on the moto in the late morning (or maybe even around noon hour, if you loitered around enjoying that third cup of coffee), and head down the road.

Eat at McDonalds along the way
It's predictable, it's stress-free, you know what it's going to cost, the Wi-Fi is free and fast, and they'll always give you lots of paper towels to use to clean your visor and your windshield.

Carrying food with you on the moto is very risky - the food might spoil from the heat, and if that happens, you won't need Psyllium to promote peristalsis - you'll be able to sh1t through the eye of a needle from 10 meters away, and that's no fun at all.

Ride until you decide you have had enough...
Then, pull out your smartphone, launch TripAdvisor, and look for a good hotel nearby. You'll always find one within about 15 minutes of wherever you are. The TripAdvisor app will tell you what the prices are and whether they have space for the night, and the reviews will tell you whether the place is worth a visit or best avoided.

Consider riding at night
It's cooler, there are fewer cars on the road, and it's generally less stressful than riding during the day. If you got a late start in the morning (or early afternoon), and you're still going strong when the sun sets, why bother stopping?

Ride Alone, never with others
Riding with others just adds stress to the whole trip. If you travel on your own, you have control over your schedule and your itinerary. You can "go with the flow" rather than having to "stick to the plan".

Always be open to the idea of staying in one place for a few days
So, you checked into the hotel, the staff were friendly, the property is tranquil, you had a nice dinner and a good night's sleep... why leave in the morning? When you get that wake-up call at 10:00 AM or 10:30 AM, just tell the front desk that you'll be staying another day, hang up the phone, and go back to sleep.

Regards,
Michael