2 Weeks in Scotland - What would be realistic?

You may not want to take tours, but in some cases they will be the most reasonable and efficient way to see the things you have on you list.

This is true especially if you are not used to driving on the left side of the road in a car with the driver's seat on the right.

In general, I'd say the places you want to go are spread out and that the travel time to get to them by any means of transportation is longer than you might expect. Some may not be easily reachable by car, or indeed reachable at all except by a tour.

Keep in mind that 2 nights in a location really only gives you 1 full day there. I spent 4 nights in Kirkwall on Orkney and still didn't see all I wanted to see.

I took a Northlink ferry from Scrabster to Stromness and a public bus from there to Kirkwall. I flew from Kirkwall back to Aberdeen. The Northlink Ferries websight I linked has lots of tourist information along with transportation routes and timetables.

While in Kirkwall, I took a day tour to see all the sites you have on your Orkney list and more. I found the tour at the Tourist Information office in Kirkwall, right next to the bus station. I was the only person on the tour. It was done by a former school principal. If you Google something like "day tours from Kirkwall," you'll get lots of results to consider.

You will not be able to spend any nights on Staffa. It is an uninhabited island. Fingal's Cave is there. Your best bet will be to take a tour of some kind.

A Hairy Coo day tour out of Edinburgh could hit some of the places on your list all in one day. There are several listed on the page I linked. I did one in May, 2016 and had a blast.

On that tour, I learned that the best time for heather is August. This link to Scottish Heather is about that.

Weather is always iffy in Scotland. May was cold and wet with sideways rain on the day of my tour on Orkney. Fortunately, I was well-prepared for it, but if I went to Scotland again, I'd go in late August when the heather is blooming.

Exactly how many nights would you be able to spend on the ground in Scotland (not counting the overnight flight heading there)? I think you've got too much for two weeks. Orkney, Skye and Staffa are all time-consuming to reach. Visiting Staffa would probably mean getting yourself to Oban, then to Mull, then to Iona, and from there to Staffa. West Coast Motors runs a tour that begins in Oban (with tickets for the ferry to Mull), which I believe is the simplest way to get there. I don't know that there's any way to avoid spending two nights in Oban in the process.

I found a lot to do in both Edinburgh and Glasgow, but I am a fan of both interesting architecture (which Glasgow has tons of) and museums (which both cities have). I'd suggest digging into a guidebook or two to figure out how much city time you'll want; that may limit what else you can see.

You should consider that the weather in western Scotland (and I suspect also in Orkney, though I haven't checked) is very unpredictable. It rains very often. I believe it's actually wetter in July/August than in May/June (verify that if it matters to you). If you plan to be somewhere like Skye for only one day, you could end up with a total washout. I saw much of Skye through the windows of a local bus with rain sheeting down the windows. It's best to spend at least 3 nights there so there's a decent chance you'll be able to see your top target(s) on one of your two full days. If you want to do some walking outdoors (as for the Old Man of Storr), you might consider taking a pair of rain pants as well as the definitely-required waterproof rain jacket.

It's worth taking a look at Rabbies multi-day tours to see whether that company has something that hits enough of your must-sees to be worthwhile. I bet Rabbies' professional drivers can negotiate the rural Scottish roads faster than an American tourist. Unfortunately, they can't do anything about the rain, so that risk will remain. One advantage of a tour is that it would relieve you of the burden of booking lodgings for that part of the trip.

Lodging in Scotland is a bit on the expensive side. The supply of rooms on the islands and in the western ferry port of Oban doesn't seem to have kept up with the recent increase in demand. August sees a sharp uptick in Edinburgh hotel prices because of the various festivals taking place then. The always-crowded Old Town becomes even more so that month. I don't know what will happen next year: Will demand be severely depressed? Will many of the hotels and B&Bs be closed due to bankruptcy, suppressing supply? When I was planning my 2019 trip I had a lot of difficulty finding affordable lodging along the west coast and on Skye and Mull. I needed a room with twin beds, and I had started looking in December for a July trip.

On the islands it is advisable to make dinner reservations if you want to eat sitting down. There's also an inadequate supply of restaurant tables.

Flying in and out of Inverness sounds like a bad idea, it is a small airport with a limited number of flights. Flying to Edinburgh or Glasgow makes more sense.

That is a lot to see but doable. It it was me I would cut down the number of places a bit though in order to make the trip a bit less rushed. But you could do something like this:

Edinburgh (including day trip to Stirling castle): 3 nights. Train to Aberdeen.
Aberdeen (day trip to Balmoral Castle): 1 night. Ferry or flight to Kirkwall
Orkneys: 2 nights. Visit Skara Brae, Ring of Brodgar and Maeshowe by tour or rental car. Flight or ferry to Inverness.
Inverness: 1 night. Rent a car and drive to Skye via Loch Ness.
Skye: 1 night. Visit Old man of Storr. Drive back to the mainland via the Mallaig ferry. Stop in Glenfinnan to see the steam train.
Fort William: 1 night. Drive to Mull via Glencoe and Oban.
Mull: 2 nights. Tour to Staffa. Drive to Glasgow (or if you can, return the car in Oban and take the train to Glasgow).
Glasgow 2 nights, fly home.

This doesn’t sound very realistic to me given the distance and the time it takes to get out to Orkney and back . Much less see something.

Day 10 Ferry to Orkney, see the neolithic sites
Day 11 Drive to Loch Ness

I took the 3 island tour from Oban. It went to Mull, Iona, and Staffa and included ferry and bus transportation. It was very efficient and less expensive than taking your car on the ferry and driving it yourself.

Rick has a good video about this short section that you might enjoy watching if you haven't done so already. I think it gives a nice taste of the area.

https://www.ricksteves.com/watch-read-listen/video/tv-show/scotland-islands

Our typical trip includes careening around the countryside, making one-nite stops in each port of call. Our next trip will be at least two nights in each stop (three in Orkney). My tentative itinerary includes all your stops except Balmoral and includes a lot more hiking. We're using Pentland Ferry to Orkney, and because we're a party of four, two of us can ride the Jacobite while the other two drive, allowing us to go one way to Skye. Our plan is slightly complicated by wanting to do a couple of Celdaihs (Oban, Edinburgh) and Parkruns (Fort William, Edinburgh). Without those constraints, the trip could be a lot slower paced.

That’s up to 8 or 9 hours of travel including getting to ferry terminal, waiting around etc. It doesn’t sound very pleasant to me. Every traveler is different though.

Not only do you get to see the countryside and run into cattle jams, but you save $200pp in airfare, the stress of airports, and the cost of a rental car in Orkney. As a party of four, our decision to drive from Inverness to Gills Bay is a no brainer. You can stop at Whalingoe Steps, then when you get to St. Margarets, you can visit Tomb of Eagles on your way to Kirkwall. With a rental car, you can arrive at Brough Birsay at the right time for the tide, and take advantage of the late sunlight with all the 24hr attractions like Cuween and Gurness.. You can even take a quick photo under the John o'Groats road sign! The Pentland ferry is quicker than the Scrabster ferry and I believe it is more tolerant of marginal weather. Of course if the normal schedule isn't restored, the midday ferry is cancelled which messes everything up.

If you plan to ride the Jacobite steam train, set aside a full day for this. It was just under a 2-hour drive each way from Inverness to Fort William when we did the drive last August to take the train. In retrospect, I would have found closer lodging for that portion of the trip. It was a long day. At least the scenery was beautiful and took us along Loch Ness.

That being said, the train ride is spectacular! I booked first-class cabin seats 9 months in advance at 50 pounds/each. Seats are more comfortable and include tea and cookies. If I were to do it again, second class would be just as nice. Book your seats as soon as you have locked in your travel plans; tickets go fast. The ride is about 2 hours each way, with about 2 hours or so to stop in Mallaig. There isn't much in Mallaig other than super fresh seafood, so it makes for an excellent place to grab a fantastic seafood lunch and a pint of beer - but, I would advise to be quick about it because everyone else getting off the train will be thinking the same thing.

One alternative for the steam train if your party includes two drivers is stop in Ft.William, let half the group ride the train and the other half drive to Mallaig, rejoin at the ferry, then when leaving Skye, do the opposite, so everyone gets a train ride and you never lose your rental car. The driver has "seen" the train during the drive to Mallaig, so if riding it isn't a big deal for them, you can exit Skye via the bridge and see new ground, which is what we plan to do.

We enjoy the experience of careening around narrow roads with obstacles like tractors, cattle, and tour buses. Not having a rental car just isn't something we'd do. Timing a visit to Birsay with the tides is almost impossible with a tour. Low tides always seem to be at the wrong time. I actually look at the advance tide tables to route the day, in 2022 for now.