Train ticketing question

For St Andrews you take the train from Edinburgh to Leuchars and then a short bus ride. From Anstruther you will need to get back to Edinburgh for a direct train to York.

York to Windermere is an awkward train journey. National rail offers a train from York to Preston, then Preston to Oxenholme and then Oxenholme to Windermere. Alternatively Your to Leeds, then Lancaster, then Oxenholme and then Windermere. You can probably also go via Leeds, Carlisle and Oxenholme. Even conceivably via Newcastle, Carlisle and Oxenholme. All perfectly doable but I think at least 3 and a quarter hours, maybe longer.

Windermere to Manchester Airport is much easier - some direct trains, others needing a change at Oxenholme.

Assuming you can book a specific train then for most of those journeys booking now should find cheaper prices. If "we" is two people, or a multiple of two, then a TwoTogether railcard nat a cost of £30 will give you about 1/3rd off all fares.

I imagine Stuart (isn31c) will be along to offer some more detailed information on routings.

From Anstruther there are buses direct to Edinburgh. Or the same bus to Leven, then the train to Edinburgh for York.
Every few hours you can change from Leven at Kirkcaldy instead into a train from Aberdeen to York (heading to London).
So far I seem to be the only person on this forum to have used the new Leven Station.
You can always buy on the day, but will save substantially by buying ahead for fixed trains.
Use the Scotrail website as they will split the fares for you (for free) to give you the best deal, and tell you how much you are saving.
As you say 'we' buy a Two Together Railcard for £30 which will save you 1/3 off all rail fares after 9.30 am weekdays, all day weekends.
There are at least three ways from York to Windermere. Usually the cheapest is the hourly York to Preston, change there for Oxenholme (possible 2nd change) and Windermere.

As an example of the savings to be made (before railcard reductions), all fares for 3 weeks today.
Edinburgh to Leuchars £9.80 vs £18.70 on the day;
Leven to York £47.20 vs £67.60 on the day;
York to Windermere £19.50 vs £83.50 on the day, on the 0922 via Preston;
Windermere to MAN £12.10 vs £32.30 on the day, on the 0955 direct.

All the above cheaper fares are on specific fares, the higher ones are fully flexible.

To Johnew52 and to isn31c
Thank you both for your helpful replies. I very much appreciate it! NOW, i have another inquiry: Our original plan during our stay in York was to travel (via bus) over to Grassington for one night, then returning to York early on the morning of October 17 to catch the train to Windermere. welll... Nothing on the Stagecoach site. Do you know if there is a bus service between York and Grassington? It looks like we need to be back in York by at least 10AM to catch the train to Windermere.

10 October is a Thursday- the York to Grassington bus runs only on a Sunday.

So what you would do is to train York to Leeds (multiple services an hour) then Leeds to Skipton (2 or more per hour).

Then the Transdev Keighley and District Bus 72 from Skipton Station to Grassington- https://www.transdevbus.co.uk/the-keighley-bus-company/services/72/

Then the #72 back to Skipton and the train from Skipton to Lancaster, change, Lancaster to Windermere. They are every few hours so the 1015 bus arrive 1048, Skipton depart 1057, Lancaster arrive 1`212, depart 1303 direct to Windermere arrive 1354.

An advance fare (train specific) 3 weeks today on the 1057 is £11.10

I think that 1015 is a bit tight. I might be inclined to get the 0908 in, arrive at the Railway Station at 0943.

The York to Skipton fare- always split that as York to Leeds for £4 to £7, then Leeds to Skipton for £5.80. A full flexible fare is £31.20.

The Skipton to Windermere full flexible fare is £32.90

You would be going way out of your way to return to York from Grassington then to Windermere.

That would be like going from Seattle to Portland (OR) via Spokane!

Wow. amazingly helpful information isn31c. Thank you!!