Traveling Scotland without reservations?

Just a question, you say "we" are travelling, but then say "I" don't want to be tied down to a set schedule.

What does you travelling companion have to say?

Are they the kind of person who likes to live on the edge and would be happy not to reserve accommodation, or are they going to prefer to book in advance and stick to an itinerary? If you are travelling with someone who does not think as you do, not booking accommodation may cause a whole heap of otherwise avoidable stress.

In May and therefore early in the tourist season you would probably get away with not booking accommodation, but you will have to accept whatever is out there when you are travelling. It may not be what you would like, or even where you wish to be. It only needs a wedding, golf tournament or some other event to ensure that in smaller towns and villages any accommodation has already been booked by others.

There is no doubt Scotland is riding a tourist wave at the moment and is a very popular destination for all kinds of reasons, although the television series Outlander has definitely played a part.

If you are set on not booking ahead, then join AirBnB so that you can use their instant book facility and use the Visit Scotland website to get lists of suitable accommodation to look at as you travel around. It's always worth using Google maps as well because not every B&B will be listed with VS.

However you should not go to Skye without securing accommodation before you get there. At any time of year.

How many people are in the traveling party?

Agree with the above. I'd just add this: keep in mind that some (almost all) of the places you want to go are rather small towns, with limited (sometimes very limited) options available for lodging. Small towns often have only a handful of places to stay. If the best are booked up when you roll in, you can end up in someplace that does not come close to what you have been dreaming of (in worst cases, you might have to move on to someplace else, so I would not leave the task of securing lodgings until late in the day). If you're OK with grinning and bearing it, making do with something basic that just meets your critical needs for shelter, then that's the bargain you make. Agree that you should be ready to include AirBnB and other services so as to cast a wide net as you may need to be more flexible than you think.

Personally, I concluded years ago that getting "locked in" to an itinerary long in advance, so I can be assured of decent lodgings, does not limit me in any way, and in fact, actually frees me to enjoy my time more and results in a better trip. 'Tis a paradox but has proved true for me. For me. I'm done arriving after dark and roaming around, searching online, comparing, weighing places trying to find something good enough, often paying too much and settling. I'd much rather be sitting by the seaside enjoying a glass of wine, or in a pub with a pint catching some trad...but that's a choice I consciously made years ago. YMMV.

I'm a wing-it traveler when I feel it's safe to be, but that doesn't mean that I book rooms on the day of arrival. At the very least, I book them the night before, and I usually check a few days ahead of time on booking.com to see what might be available for me. That provides an early warning sign of no-room-at-the-inn. I think it will be easiest if you're looking in places that are not served by trains or buses, which you will be free to do since you'll have a car. The easily-accessible spots fill up very early.

We will be renting a car

How many is 'we'? Finding a single room may be not too difficult. Finding multiple rooms all in one establishment may be a challenge

touring mostly whisky inspired locations

You have a designated driver? DUI is 0.05% ( vs the more common 0.08- to 0.10% in the US)

All very good points. Thank you. Perhaps this isn't the right time to go out of my comfort zone.
The "we" is my husband and two friends, one of whom doesn't drink. My husband hasn't participated in planning in the past. He just asks in the morning "where are we going today?". It's both good and bad. I get to plan what I want. But, sometimes I feel like a tour guide.
I'm going to stick with reservations. Thank you for the reality check.
J

Now that we have the lodging situation straightened out, I'll advise you that in the summer (which May is not, I know), you really have to make dinner reservations if you want to eat your evening meal in a restaurant in one of the coastal villages, however casual. I have no idea what the situation will be like in May. I would inquire of your hotels.

Regarding your itinerary, I don't see any reason to avoid Loch Ness as it is right on your way between the Elgin area and Isle of Skye. We found Urquhart Castle well worth a visit. It's a ruin (so you need to dress for the weather), but it features lots of interpretive signboards, and there are frequent walking tours (included in the entry fee) as well as costumed interpreters.

If the Nessie legend interests you, the Loch Ness Centre & Exhibition at Drumnadrochit is a reasonably fact-based examination of the history and science surrounding the sightings. And it's indoors so a good choice if the weather doesn't cooperate.

You might get the best mileage out of your itinerary if you can fly into Edinburgh and out of Glasgow (i.e., open jaw).

Since you're interested in whisky: on the drive north from Edinburgh to Inverness up the A9 you go right by the Dalwhinnie distillery, so that might be worth a stop. Dalwhinnie was our fave of the whiskies we tasted in Scotland. Of course, keep in mind that Scotland's DUI laws are very strict!

Hi Jacqui
I would definitely booking your B&Bs ahead of time. Skye in particularly is into full season mode in May and you will also need to book dinner reservations here on Skye. Most B&Bs would be unlikely to be able to provide 2 rooms that haven't been reserved in advance. Speaking for my own B&B, well we only have 2 rooms, and we would expect to be fully booked from April until the end of September within 2 weeks of opening our rooms up for reservations (which we don't usually do until February).

If you want to do a distillery tour of Talisker you will also need to book that in advance of your visit and can do so online. You might also be interested in the distillery on the island of Raasay which is located a short ferry ride across from Skye. Raasay is a wonderful, very unspoilt island and it feels like stepping back in time when you go there. Having said that the distillery is bang up to date and also sells gin.

Hope this helps
Jacqui (Skyegirl)

I've done it in july and it worked with a bit of flexibility. But my prefered way would the book most accommodations ahead of the trip.

If you know where you’ll be each night, then it doesn’t hurt to have a reservation, but that locks you into an itinerary with no room for spontaneity. Winging it allows you more freedom to diverge from your original plan to take in something that was unplanned. It’s really a personal choice. If your itinerary takes you by Loch Ness, you may as well stop.

Looks like OP had already made a decision. But having researched Scotland quite a bit lately, it’s a country that seems on the expensive side for accommodations and there are a higher proportion of places that look just so-so and/or have lower ratings on Booking.com. This is a function of supply and demand and how built out the tourist infrastructure is, is my sense. Or maybe the B&Bs don’t list on that site. Ireland is a country where it seems B&Bs are so plentiful you might still be able to do it, book on the fly. I always say if one does not want to spend time looking for rooms before a trip, why waste actual vacation time doing it as you go?