Hi there- My husband and I will have 4-5 days in Scotland in May 2020. We will be doing some genealogy in Dundee and wonder where else might be best to visit as well. I'm looking at Aviemore. No big cities for us, thanks.
Also- we prefer to travel by train. We'll be flying in and out of Edinburgh. Thanks!
You might want to consider Arbroath and Montrose. They're both on the rail line. Stonehaven is a little farther afield, but it's also on the train line. You could visit Dunnottar Castle from there. Broughty Ferry, which is just outside of Dundee, has a nice beach. Buses are available from Dundee to take you to places like St. Andrews and Crail.
If you decide to go to Pitlochry or Aviemore, you'd have to switch trains in Perth.
Dundee has a lot of very good restaurants. I'd recommend the Tailend, in the Nethergate. Very good seafood restaurant, as the name implies. The city is also home to two world class universities, so there is no lack of nightlife, after you've spent your daytime hours doing genealogical research. There are also several excellent museums, including R.R.S. Discovery, Verdant Works, the McManus Art Gallery, and the new V&A.
Good luck with your research.
p.s.: D.C. Thomson, the publishers, are planning a new museum of historical comic strips ("Dandy," "Beano," Oor Wullie, the Broons, Desperate Dan, Beryl the Peril, etc.). It may be open by the time you get there next year.
p.p.s.: I'd recommend the Premier Inn Dundee Centre as an excellent place to stay. The rooms are clean and comfortable, and there is an on-site restaurant. Ask for a room overlooking the River Tay. As you're planning this trip far in advance, you should be able to get a good rate. Last summer (late June), we were able to get a room for 35 pounds per night from the Premier Inn website. The hotel is directly across from the train station, and next to the R.R.S. Discovery and the V&A.
So here's where you can find a rail map for Scotland. If you look at the map you can go east and north from Dundee--that will take you to Arbroath--have a smokie for lunch. Alternatively, you can go east to Perth and then north. Heading north you can visit Dunkeld and Birnam, It is a great place to enjoy the Tay River, the woods, the hills, the two small towns. There are two sites to check out walks, here and here. Further north up the line is Pitlochry. I love the Explorer's Garden. There is a distillery, and there is the Festival Theatre, but I don't know that they do matinees. You could go a bit further to Blair Castle. You will want to check the train schedules to see what the timing would be.
Another vote for Arbroath. We spent a day there last summer while visiting friends in the area. We walked along the coast path for several hours in the morning and spent the afternoon at the Abbey - now ruins for the most part, but still very interesting.