Thoughts on our itinerary

It's hard to give a good bit of feedback, because I've been to some, but not all, of the places you are considering. So I can't say X is better than Y.

I will say I really enjoyed Pitlochry as a base for doing some delightful, and mostly level, hikes. You say "mild walks," so I'm not sure what qualifies. One day I took the train to Dunkeld and Birnam, visited Birnam Oak, and hiked the Fiddler's Path along the River Tay. (This could be as mild as you want, since you can turn around and head back to town at any point.) Dunkeld Cathedral is also worth a visit, and as Rick Steves and Fodor say, the town is appealing and beautifully preserved. It was a very short train ride from Pitlochry (about 15 minutes). Since you'll have a car, you could drive.

The other hike I did started and ended in Pitlochry. It combined two hikes: Loch Faskally and Linn of Tummel. This was a much longer hike (about 5 hours), but again, you can shorten it to your taste.

Enjoy Scotland!

Arrochar is a lovely wee village to stay, on the shores of Loch Long (just away from the tourist crowds) with several places to eat, including the great restaurant in the old Church at the railway station between the two villages (Arrochar and Tarbet).
The only though would be that the village IS in the Loch Lomond and Trossachs National Park- the thing being that the NP is a hybrid- Loch Lomond and the Trossachs are two different places.

Thus while I would unhesitatingly recommend Arrochar as a place to stay, it is not ideal if your emphasis is on the Trossachs. For that purpose Callander would be better. I like Callander but it does get pretty busy. Somewhere else in the area such as Aberfoyle might be a better bet.

There are always compromises in these things. Callander/Aberfoyle are on what some see as the nicer route to Oban (via Lochearnhead) but then Inveraray is a short diversion off it, whereas Arrochar is directly on the Inveraray route.

And offer me a straight choice between Pitlochry and Dunkeld, and I'm going to choose Dunkeld any time.

Also I wouldn't stay in St Andrew's with a car- I would probably choose to stay in one of the East Neuk towns, such as Anstruther.

In the Borders I'm not really going to even try to split the various towns- Peebles is as good as any of the others.

I don't think Option B is that rushed, at least it isn't one night stays. Personally I would swop a night off either Tobermory or St Andrew's to reinstate 3 nights to Peebles.

That is a difficult choice...

Glasgow can be done as a day trip on the train from Edinburgh.

Looking at Glasgow to Tobermory - that is going to take up most of the day to get there - it’s going to be about 3 hours drive (allow plenty of time for slow traffic! and check in time is 30 minutes before the ferry sails). Looking at the current timetable you will probably be pushing it to make the 12.15 departure and the 14.15 departure is probably more realistic so you are unlikely to reach Tobermory before 4pm.

I like the choice of Arrochar as it also gives access to places like Inverary (with its castle) as well as the Cowal Peninsular with the wonderful Benmore Botanic Garden and possibly across to Bute. you could spend a day exploring Oban area along with Kilmartin Glen and into the top of the Kintyre peninsula . 2 nights in Arrochar doesn’t give a lot of time there.

If going for the second itinerary. My suggestion would be to cut Peebles from the itinerary and add an extra night to Tobermory and one to Arrachar OR add two to Arrochar... (and that is coming from someone who really likes the Borders area too...)

I see from your posting history that you've planned a few Scotland itineraries over the years. So it sounds like you've done a good bit of research already.

Can you fly into Edinburgh and out of Glasgow or vice versa?

Have any already decided which courses you will play? Many, many years ago we golfed at several local courses, not the big names, and always received a warm welcome and found each place to be a different experience with beautiful views.

Besides visiting castles, would you be up for staying in an authentic castle? There are several lovely places. In 2023, near Oban, we stayed at the 17th century Barcaldine Castle which now operates as a B&B. Oban gives you easy access to the islands of Mull, Iona, Lismore, Kerrera by ferry. The Oban Distillery is in town along with several castles/ruins in the area and wonderful seafood restaurants. There are several golf clubs less than an hour from Oban including the scenic 9 hole Craignure Golf Club on Mull and the Glencruitten Golf Club just outside of Oban.

Or look at Aberdeenshire with its many castles. Leslie Castle is now a guesthouse. Your less than an hours drive to the Speyside Cooperage, many distilleries including Balvenie and Glen Gairoch and loads of castles from the beautiful Craigievar Castle to the ruins of Dunnottar Castle on the coast as well as golf courses along the coast with fantastic views like Cullen Links and Cruden Bay.

Something that may be of interest to your group: community-owned pubs.
https://camra.org.uk/community-pubs

Thank you for the replies- they are very helpful! 3 out of 4 of us play golf, so going to a local course would be fun, but we’d probably play just once. We’d have to rent clubs too which hopefully isn’t a problem.

I think we have to choose between going to Mull or going up to Perthshire. In earlier itineraries, I did want to go to Ballater- thought we’d like going to Stonehaven and doing the walk to Dunnotar. But then I thought we’d be driving too far. For the same reason, that is why we are skipping Skye. Could we skip staying in Peebles and just do a Borders tour from Edinburgh? Yes, but with 3 nights there we could see Peebles and Melrose, go visit Abbotsford and Mellerstain House, and maybe also go to Berwick or St Abbs etc.

I love the idea of staying in an actual castle! We will look into that. Maybe we should skip Glasgow for this trip too- I’m more interested in smaller local places. Plus, we are already staying in Edinburgh.

Could we skip staying in Peebles and just do a Borders tour from Edinburgh?

Yes there's no reason not to do that. Distances aren't that far and you can easily hit teh high spots in a day. Have a look at the Border Abbeys or Selkirk and Langholme suggestions on the Undiscovered Scotland website.