Would it be crazy to only book lodging for the cities, leaving several nights free so we can go where the road takes us? (traveling early September) We would have our smart phones (and eyes and ears) to find lodging as we go...
Based on our last trip to Scotland in September 2023. I would not play it completely by ear. We were 2 couples and I prebooked everything 2 months in advance. And even then, I couldn't always book my first and second choices. Every single place we stayed was completely booked by the time we checked in. Even restaurants in the middle of nowhere were booked up.
If you're not picky about accommodations or location, maybe keep an eye on booking.com or similar, and grab something a day or 2 ahead. But know that you may need a bplan B, C or ...September is still high season. Good luck!
You'd be better off booking the highlands and winging it in the cities. There's lots more unoccupied land than lodging out in the highlands-and if you're thinking about Skye, it can totally book up in September.
(source: ask me how I ended up in a Holiday Inn Express in Inverness after the cottage on Skye cancelled two hours before we were due to check in)
I suppose if you have a really high budget you might be able to find something more easily in one a,of the deluxe lodges/palaces
You don't say where you are intending to go in Scotland, but there are vast parts of the country which are barely if at all visited by most of the people on this forum.
There is a big wide world of glorious Scotland out there.
Get outside that handful of honey pot locations and there is way less of a problem.
The Scottish schools go back in the middle of August and the English ones at the start of September so it is certainly not high season for domestic tourism.
The days of 'winging it' are long gone, especially in rural areas.
Get outside that handful of honey pot locations and there is way less of a problem.
I'm not sure about that - one of the problems with rural Scotland is that accommodation can be few and far between. Much of it will have been booked for months. The days of hanging a B&B vacancy sign along the road are long gone.
You could end up either spending a lot of each day trying to find somewhere to sleep that night, and it may not be the area you want to stay and involve a long drive...
Your chances of finding somewhere in a big town or city are much better than in the rural areas.
Oh and by the way, you can't park in a layby and sleep in your car overnight either...
My brother tried to wing it on a trip to Scotland a few years back. They had taken a tent but ended up having to camp for pretty much the whole trip because every hotel or B&B was fully booked. They were very surprised to find this was the case. I think there were some very expensive high end options available but nothing at a more moderate price point.
In short - yes it would be crazy. I have lost count of the number of folks coming to my B&B door to ask for a room, only for them to be surprised when I tell them that my rooms book up for the summer season within a week of me opening my diary in January or February. Since the Short Term Lets licence scheme was introduced a couple of years ago, many smaller operators have closed considering it not economically viable to continue B&B. You would likely spend many fruitless hours searching for accommodation and might end up sleeping in your car. I often pass cars with steamed up windows (the occupants having slept in the car - illegal to do this in lay bys) as I head out to get my groceries early morning. Any accommodation you do find is likely to be the less desirable places that nobody else has booked. Even in September the Highlands and Islands are very busy, as despite the schools having returned many adult couples choose September to take their holidays.
Since the Short Term Lets licence scheme was introduced a couple of years ago, many smaller operators have closed considering it not economically viable to continue B&B.
Exactly what friends of mine decided to do having gone through various Covid lockdowns and realising they could manage well enough without a B&B income. The license was another financial hurdle and simply applying for one was no guarantee of success in being granted one, so they stopped the B&B side of life and undertook voluntary work instead.
If you do want to wing-it then you may have luck finding accommodation by taking to social media rather than looking on Airbnb or other booking platforms. There are lots of Scottish travel Facebook groups out there as well as community groups. I've seen requests for accommodation from time to time on local FB pages so it might work for you.
You don't say where you are intending to go in Scotland, but there are vast parts of the country which are barely if at all visited by most of the people on this forum.
And that's understandable. Most people have a limited time to travel and are anxious to see the beautiful places they've read about and seen in photos. It's the same in the US. I can't tell you how many Europeans I've run into and when I asked them where they were heading to, it's almost always New York, San Francisco, Las Vegas, the Grand Canyon, Utah, Arizona and Florida. Of course it's wonderful when you have a large chunk of time to travel and can visit all the lesser-known places, but most travelers don't have that luxury. :-)
And I agree with Wanderbug that if you do what you are suggesting, you book in the Highlands and wing it in the city. It would be easier to something more last minute there. I wouldn't do it, though. I used to, many years ago. I loved booking my first hotel and then winging it for the rest of the trip, but it gets harder and harder to do that now, especially in places like Scotland where the ratio of lodging to tourists is very low.
We had a glorious trip in 1997 to England, Wales, Scotland, and Ireland, and started with only our first night booked. After that, it was the Rough Guide, payphones, and looking for vacancy signs. We always found a great place (eventually).
The internet ruined all that. Our May 2026 trip has been completely booked since mid-July.
jjgurley, yep, the internet has many advantages, but it ruined a lot of the spontaneity of travel. I
But I do remember the advice about always booking your first night ahead of time, so you don't have deal with finding a place while jet lagged. :-)
I agree with others here, I wouldn't leave accommodation bookings to chance. I think it would be hard to enjoy going where the road takes you if you have no idea whether you'll be able to find a place to sleep that night. Honestly, even in the big cities it can be difficult if you want something decent that's not super expensive.
I strongly agree with Mardee: "Of course it's wonderful when you have a large chunk of time to travel and can visit all the lesser-known places, but most travelers don't have that luxury." It's very true, and if I'm flying halfway across the world, I'm definitely prioritising those places I've read about. Also, those places tend to be well known for a reason- because they are exceptionally beautiful, or unique, or something exceptional happened there...
Mardee, thank you for your response to lesser known places.
Maybe we can share some of the USA's many lesser known places that never see a foreign tourist when he our vast country.
Theorietically winging it is still possible. Unfortunately depending on where you are going the possibility is the same as my chances of being in the starting XV next international at Murrayfield!
The smaller the place or the more Edinburgh the place I would book. You are more likely to be able to wing it in Glasgow or Dundee.