Help Planning a Walk in Scotland

I suggest you look at Celtic Trails and Mac’s Adventures. There are several trails to choose from, and they can advise you on the best fit.

Macs is a well-established company that offers the type of walks you describe

https://www.macsadventure.com/tour-listing/?rgid=265&lcntyp=L&mactids=1&sactids=5,6,8,17,18,19,20,21&rbdid=

Another is Contours https://www.contours.co.uk/scotland

and there is HF Holidays https://www.hfholidays.co.uk/destinations/united-kingdom/scotland

too much choice....

The John Muir Way crosses Scotland coast to coast, and there’s a walking, in addition to bicycling and horseback route. You can even get a trail passport and get it stamped along the way to document your progress. We’d planned to do it in summer 2020, but the Pandemic has postponed that for now.

It apparently takes 9 to 11 days to walk the entire route, although it certainly seems that you could do a 4-5 day portion. it wouldn’t pass just outside your front door in St. Andrews, but wouldn’t be too far to get to Edinburgh or other starting/stopping places along the Way. The Website https://johnmuirway.org/ provides many details, including several tour companies that can handle arrangements for you, including luggage transfer.

You might also check out Wilderness Scotland. I know people like these long walks, but another way to get 7 days of walking is to park yourself in a location that is convenient to different parts of the country and you go where the weather is good. The person who used to do these trips no longer does them so I can't recommend anything, but it worked well.

The John Muir Way, from Muir’s birthplace in Dunbar to Helensburgh on the coast near Loch Lomand, is a fairly new long-distance trail, opened officially in April, 2014. We were heading to the UK in May of that year to walk, thinking of the West Highland Way, but I was also attracted to the idea of walking the brand new John Muir Way. I thought I might have a shot at being one of the first to complete both the John Muir Way and the US John Muir Trail in the Sierras, which I did in the summer of 1970. After investigating, it seemed to be much better as a bicycle route than a hiking trail, so we looked at other options—-the West Highland Way, the Great Glen Way, the Rob Roy Way, and the Speyside Way, which was particularly recommended to us by Celtic Trails.

In the end we opted for a sort of “UK sampler” that included 2 weeks of walking in Scotland, Wales, and England (Shropshire and Cornwall) rather than a single long walk. Basically, it all sounded so good we couldn’t make up our minds!!!

If we were to go back to do one of the full walks, I would probably use HF Holidays, as we have had very good experiences with their lodge-based walking holidays in the Lake District and the Jurassic coast. They have guided treks on the West Highland Way (9 days of walking the full route), Great Glen Way, and others.

https://www.hfholidays.co.uk/holidays-and-tours/west-highland-way

My reasons for choosing this are (1) we like the camaraderie of the other guests (mostly Brits), and (2) we learned from our prior experience with the self-guided treks in Wales and Shropshire that we are pretty bad at figuring out some of the route directions given—-things like “keeping the dingle on your left, cross the field (usually full of sheep or cows) to a stile by a gate on the far side, then aim for the solitary oak tree and find a gap in the hedge . . . .” We chose the wrong gap (or the wrong hedge) and only got it sorted out when I read that the next step involved a tamarack grove on the hilltop—-fortunately I knew what that was (larch trees) and found the path again.

Since then we have chosen guided walks for our foreign trips (Tour du Mont Blanc, Milford Track in New Zealand, the W in Patagonia, and others.

The Fife Coastal Path is located near St. Andrews. It is considered one of the top Seven Scenic Walks of Scotland. The other Six in no order are: 1. The Lost Valley, Glen Coe, 2. Glenfinnan Viaduct Trail, 3. The Quiraing, Isle of Skye, 4. Arthur's Seat, Edinburgh, 5. West Highland Way, 6. The Hermitage, Perthshire, which is a National Park. Look these up on Visit Scotland.

Thank you everyone for the insightful information. Researching all your suggestions and fingers crossed that Covid does not cancel (again) this trip.

Another vote for Mac's.
I haven't used them, but my close friends did the West Highland Way with them a couple of years back, and loved it...great hotels.

We used Contours a few years ago for our West Highland Way adventure. I would use them again if I were so lucky to be walking in Scotland again.