London/Scotland

There are nonstop flights from YYZ to Edinburgh (EDI) / Glasgow (GLA) and London (LHR) to YYZ. You’ll need to click on the multi-city button when bringing up your flights. Check the prices for one-way travel too.
While in Scotland sleep in Edinburgh and visit Glasgow as a day trip from Edinburgh. I would also work my way up to the Highlands on arrival day.

Two weeks is not a lot of time to see London, Edinburgh, Glasgow and the Highlands, along with your time at your time share. I would first figure out which place you will use for that. Perth has the advantage of being relatively close to Edinburgh. Dunkeld and Ballater, are more inland into the Cairngorms, and Aviemore would be closer to the Highlands (and Inverness).

If you want to keep all your locations, I would probably fly into London, spend at least 3 nights there, then fly or train up to Edinburgh and base yourself for several nights. You could do day trips to Stirling Castle and/or St. Andrews as well (or you could see both of those from Perth if you decide to stay there, which might be a better use of your time). Once you leave Edinburgh, rent a car outside the city.

If you decide on Aviemore, you could drive there and explore the Moray Coast, along with the Culloden battlefield, Clava Cairns, Speyside, then head down to Glencoe or Oban to explore the Highlands area for several nights.

After that, make your way back towards Glasgow, spending a day or so exploring the city, and then just fly home from Glasgow.

MaryPat thank you for the tip on how to check the airlines for multi city tickets. I certainly do appreciate it.

Mardee thanks so much for your comments. Yes 2 weeks not a lot of time for everything. Thinking will only do 2 nights at the timeshare to see the Highlands. Then will utilize hotels and Airbnb for other locations once I nail down the best home bases.

I'm with Mardee here. Don't be too ambitious in your plans, especially if you are planning to spend any time in London and Edinburgh/Glasgow. You want want/need a car in any of these places. However, once in the Highlands, a car could be an advantage, depending on where you plan to stay and what you want to do/see. Remember distances may not look far on a map but will take a lot longer to cover than you might expect. Driving in Scotland is slow. Build in time to stop and enjoy the different places.

Any of the places you mention would make a good base for a few nights. Aviemore and Ballater are more in the Highlands. Aviemore may be better if using public transport.

You have plenty of time to think about this and September/October will be a lot quieter too. Pressure on accommodation will be less, although places like Syke still book up well in advance.

The Secret Scotland website has ideas for different lengths of self drive itineraries and will give an idea of what you clould do.

What not to miss ?

That's a difficult one as my 'must see' list could be the list from hell for you! What sort of things are you wanting to do see - ruined castles and abbeys, stately homes, scenery, walking, museums and culture, sporting type activities, high adrenaline stuff, shopping.... the list is endless. Any good guide book will give you a tick list of popular ideas.

My favourite is DK Eyewitness which has lots of pictures and covers many areas not in the other guide books. The maps are also good enough for initial planning. They do a guide to Great Britain as well as one just covering Scotland. You can buy a cheap second hand copy from Amazon - the basic information won't change much but do check latest opening times on the web.

If you have 2 weeks, that is 12 nights. Save time by flying multi-city (into Edinburgh or Glasgow); 3 nights Edinburgh; 3 nights Glasgow; 2-3 nights timeshare; 3-4 nights London. Personally, I might be tempted to steal a night from Glasgow and give it to the Highlands/timeshare - bout that is personal. Others here love Glasgow. The truth is you’ll just have to make choices. Are you a city person or a country person? What specifically do you want to see? Would a return to London be possible? If so, maybe just give London a quick stop.

Wasleys and Texas Travel Mom thank you so much for your responses.

Yes we will have 12 nights. Hoping to bring my 87 yr old mother along so that she can walk the streets of Glasgow where her mother was born and walked. She's in very good shape, in fact this past May we traveled to Ireland for the first time to visit Dublin/Donegal/Belfast/Antrim Coast. I most likely will book a private tour for the Highlands. We did that for the Wild Atlantic Way and the Antrim coast and that worked really well for us.

Was thinking maybe doing London at the end of the trip perhaps 2 nights and fly out from there back to Toronto. My biggest questions are when and where to take the train and/or a rental car. Also where to fly into and which base locations would be best to take day trips from.

We enjoy both the country and city sightseeing. Castles, museums and the beautiful landscape and of course souvenier shopping. We most likely wouldn't do any "hiking" but mom did walk Giants Causeway from the bottom to the top so a walk up to a castle should be fine.