Quick trip to Scotland

My daughter and I traveled to Edinburgh the last week of October 2024. We took a day trip to the Highlands, Glen Coe and Loch Ness with Highland Experience. There was a lot of driving involved . The scenery was not lush and green but rather brown and dried out. We visited Glen Coe, Loch Ness and Urquhart Castle which were not crowded nor touristy. One option for you could be Stirling Castle which satisfies your history interest and is certainly reachable by train ( less than an hour). We did not go there because of a time constraint but if we had another day in Edinburgh we would have.

You have three spare days, not one, so Orkney and Shetland become more viable.
Potentially even the last flight on Thursday may be possible.
However, as September turns to October the chance of weather disruptions to both air and sea services becomes higher so buffer time on the way back would be highly desirable - that is returning south on Sunday night.

You say you want quaint and off the beaten path, but then choose the tourist town of Pitlochry. In the same area Dunkeld (train station), or Aberfeldy could be better fits.

I would definitely choose the September option. Weather is likely to be more settled (although still unpredictable!) and it will be warmer than the end of October. The Pitlochry area would be perfectly decent, but if Shetland is a big bucket list item for you then perhaps you could look at flying from Edinburgh (EDI) to Sumburgh (LSI).

I put in some sample dates to Loganair departing EDI on Friday 25th Sept at 0650 landing in Sumburgh 0820, which would give you basically all day on the Friday, then you could stay 2 nights, giving you all day Saturday and fly back to EDI at 1845 landing in EDI at 2010. The cheapest round trip ticket would come to £325 each. EDITED: Just seen isn31c's reply - yes you could also fly up on the Thursday evening.

You could rent a car at the airport and you should still be able to find accommodation, although Shetland wool week starts on Sunday 27th September, so people will be arriving ahead of time and accommodation does get very difficult to find during wool week itself. Wool related shops and businesses will be gearing up for wool week, and the Shetland museum in Lerwick has a wonderful exhibition year round about Shetland wool and knitting. I am also a knitter and while I've not managed to hit wool week itself (it would be too busy to me), I've been there several times in the run up and it was great.

You could choose Orkney instead and again fly up and rent a car at the airport in Kirkwall.

I would also strongly recommend September over late October. October/November are my least favourite times in Scotland, it's very dark and damp and grey. In September you may still have some sunshine. If you want to go to Shetland, you should do it! As others have said you can easily fly there and spend a few days. Just be aware those flights tend to be surprisingly expensive (I was recently looking into this myself).

Another one for September over November.

September the days are considerably longer than November, also November is after the day the clocks go back and it gets dark early. Another thing to consider is a lot of places start to close for the winter in October esp out of the cities.

I agree that there are so many wonderful places in Scotland it is very hard to narrow choices down, but as both Jackie and Stuart said, you do have the choice of flying up to Shetland or Orkney and spending two to three days there. I think that would be the only viable way of getting there if you wanted to maximize your time on the islands.

Is there any way you could extend your stay by a few days? Then you could take the train from Edinburgh to Aberdeen, rent a car, either in Aberdeen(or once you get to your island destination) and take the overnight ferry up to the islands, which is pretty interesting in itself. I love the Scotland ferries, but then again I like boats. That's I'm planning on doing next year when I head back to Scotland.

But really, whatever you do, I'm sure you will find a lot of beautiful scenery and interesting places to visit. Do you plan on doing anything in Edinburgh while your husband is working? You could follow the recommendation of visiting Stirling Castle and the town of Stirling, both of which are pretty wonderful. It's a 50-minute train ride from Edinburgh. You could also do a day trip to Glasgow, which is a fun city, although I know you said you don't really like cities that much.

Edit: One other thing I forgot to mention is Rabbie's tours. If you don't want to rent a car, there is a company called Rabbi's that offers tours to a lot of places, and many of them are based out of Edinburgh. So you could get picked up there and then visit some of the Highlands or a few other places in one day or even two or three days. They have tours of varying lengths. They come highly recommended on this forum. https://www.rabbies.com/en-us/tours/scotland