England & Scotland First time

You do realize that you will lose at least 1/2 day every time you change locations and hotels? Unless you're planning to do tours from Bath, I would cut 1 night from Bath and add to London.

What cala said. Too much time wasted in transit. Your one-night stands are basically only a few hours because of the travel time. I'd also cut Inverness.

How are you planning on getting around? Does 21 days include your travel to and from the U.K.?

You are going to be spending an awful lot of time in transit with so many 1 and 2 night stops. Two nights somewhere means only one day actually there.

I would either drop Bath and the Cotswolds (there won’t be much colour in the gardens in October) or Skye (could be very wet and Misty in October). If you drop the West Country, take the train from London to Kendal and hire a car there.

Ideally, you need 3 days (4 nights) to do Skye justice. Conwy is a geographical outlier, so possibly reconsider here? Add this night to Keswick.

Oban is out of the way, so maybe consider staying in Glencoe instead.

The usual reason for going to Oban is to take the ferries over to Mull and Iona (and possibly the small boat over to Staffa). That would be difficult if not impossible to manage without two nights in or near Oban. ViaMichelin estimates the driving time from Keswick to Oban at over 4-1/2 hours without stops, traffic tie-up (the route takes you near Glasgow), navigational errors, etc.

I liked Skye a lot, but I wouldn't go for just two nights. Aside from the need for more time to see a fair amount of the island, you need to keep in mind that western Scotland tends to be overcast and rainy, even during its best months (of which October isn't one). With only one full day and a few odd hours on Skye, you could find yourself being rained on practically the entire time. (This is also a potential issue in Oban; Inverness and Edinburgh tend to be less rainy.)

Monthly precipitation averages for October (from Wikipedia):
Portree, Skye: 23.3 days with rain (snow days not included); 8.24"
Oban: 28 days with rain or snow; 7.36"
Inverness: 13.5 days with rain or snow; 3.07"
Edinburgh: 12.4 days with rain or snow; 2.98"

Keswick is also quite rainy in October, with an average of 7.24". The Wikipedia entry doesn't provide the number of rainy days per month.

You say 21 days but only show 18 nights on your city breakdown.
I would spend 10 or 11 days in Southern England, say Bath, Chipping Camden, then London, no car needed.
Then use the balance to fly direct to Inverness ( easyjet flies several times a day ), rent a car and travel to Skye, Oban and drop the car at Edinburgh airport on your way into town before spending a few days there.
This plans gives you 3 or 4 nights in each location so that you can settle in.

You are really shortchanging London.

It’s your first time over and I get that you are excited and want a snap shot of it all. But for my two pennorth I would make a couple of changes. First I’d cut a night from Bath and add it to Conwy to give you more time in Wales. Second, unless you are dead set on going to Iona, I’d drop Oban which in the scheme of things I think is unremarkable. If you are going to Iona, you’ll need more time in Oban, at least another night as the trip to Iona is a full day affair in reality - you’ll be best on an organised trip as you have a ferry to Mull and a drive across the island to take another ferry across to Iona. And the same in reverse.

So I’m going to be controversial and say drop Oban and head to Skye direct from Keswick. It will be a monster drive but what you’ll save by missing Oban will be made up by having more time on Skye. So from Keswick, (incidentally, on the journey to Keswick I’d suggest taking the A591 through the Lakes rather than the M6 which skirts the edge of it. The M6 is quicker but not as scenic) head east to pick up the M6 near Penrith follow it north into Scotland where it becomes the A74 to Glasgow. Follow the urban motorway through/round Glasgow and head up the west side of Loch Lomond, heading north via Crianlarich, Tyndrum, Bridge of Orchy, Rannoch Moor, down Glencoe into Fort William. Beyond Fort William take the ‘road to the isles’ which comes down Glen Shiel and passes Eilean Donan Castle before heading over the bridge onto Skye. Inverness for the sake of it for me is a waste of a night - nothing wrong with it but not crucial unless you are going to use the airport or visit Culloden or Loch Ness via the Great Glen.

Weather in October can be good, ‘meh’ or downright unpleasant - you can’t order it in advance and have to work with what you get given, as is the case anywhere. In October if the weather is unfortunately unpleasant that might effect ferry sailings which is why I didn’t suggest crossing to Skye on the ferry from Mallaig. The only other thing to note that in October the days are shortening and the further north you go the earlier it gets dark - if you are travelling at the beginning of the month it shouldn’t be much of an issue, but it’s something to bear in mind. I’m sure you’ll have a great trip!

Ian

I must admit my first response was “too much -too fast.” I do realize that there are different travel styles out there and perhaps this travel time heavy schedule is a match for how you like to travel. Only you know what makes a trip good for you. I like to pack a lot into a trip, but this schedule was even a bit much for me.

My suggestion would be to narrow your focus geographically. One of the biggest challenges when planning is wanting to see it all or the fear that this is your one chance to travel so you must try to see as much as possible. How could you reduce travel times and the number a one night stays? Could you choose to think of part of this plan as your next trip after this and then focus on the remaining tinerary for this trip? I also think it can be helpful to pick the three most important experiences you want to have each week.

Good luck with your planning!