Dover the city is a dump. Dover the castle is one of the finest sites in England. Everything from a Roman lighthouse to a medieval castle to Victorian barracks to WWII tunnels/field hospital

1. As an Aussie in my late 20s that did a similar road trip last June I don’t think the itinerary is as awful as others might make out but would encourage you to cut out at least 2-3 places. The driving will fatigue you more than you think (I drove 8 hours straight last week to visit in-laws and would compare that to 3.5-4 hours (max) on the road in the UK accounting for sightseeing time and the motorways being far more bendy and narrow than what we have at home) and the weather is a factor. We had 2-3 days we were rained out and had to pivot so depending on priorities, if you don’t allow some buffer time and slow down the pace, you may miss out on things you’d like to see. Happy to send you my itinerary if it is of interest.

2. There are a few passes that provide great value. On these forums I’ve seen the Explorer Pass recommended a fair bit but I found the best value was a Historic Scotland Membership (which also gives discounted entry at select places in England).

3. Mostly yes. In smaller areas at less visited attractions you don’t need to book in advance but much of what tourists want to see need to be booked ahead of time (i.e. Edinburgh Castle).

4. Definitely book accommodation again – with the season and places you’re visiting, you’ll need to secure reservations (and accommodation will only get more expensive as you get closer to the date).

5. One of my favourite places in Scotland was Mull – it is simply gorgeous and I enjoyed it more than Skye (I’m more interested in wildlife than scenery) but not sure if time would permit for you. You’ll very much find that the journey is often the destination. The seafood is delicious (better than what we have at home, in my opinion). Give haggis a try! It is so flavourful!