Orkney Islands

i did a 3-day tour to Orkney from Inverness with Rabbie's Tours. It was excellent!

The mainland of Orkney is an easy self tour, assuming you are willing to rent a car. Three nights with two full days should be enough to see the highlights. Orkney is a pretty mild introduction to driving on the left. To see the surrounding islands and every last thing will take a few weeks.
We've been there for three nights and are returning next May for six more nights to spend some time on the northern islands and a little more of the mainland. I originally planned 10 nights, but decided checking boxes for island overnights was a silly pursuit.

I just spent 13 nights on Orkney but 8 of those were with a multi-day group tour. Before my group tour started, I did book an all day wildlife tour with Raymond Besant, Orkney Nature which was excellent although it was so windy he kept us on the East side of the island for safety. Winds were sustained at 37, gusts 47-52 mph.

I agree it would not be terribly hard to drive on Orkney if you are willing to rent a car. What are your thoughts on that? The main N-S road was developed by the military in WWII so is a good 2-lane road but many of the side roads are single track.

I might be concerned about the weather in October. I’ve been in July (2025) and mid-August (2023) and had a lot of rain and wind so I assume you’d have that plus chillier conditions. Daily temperature highs were around low 60s F.

A link to my recent Trip Report if any of it is of interest/use to you:

https://community.ricksteves.com/travel-forum/trip-reports/trip-report-seymour-travels-orkney-and-shetland-plus-edinburgh

Allow yourself buffer time between Orkney and anywhere else.

These are islands in the North Atlantic and weather disruptions to both sea and air services is not that uncommon, especially in the shoulder and winter seasons.

Orkney is not all about prehistoric remains. There are lots of facets to the island group including the vikings, a lot of war history and the Hudsons Bay Company.
Quite a bit of the war history is on the Isle of Hoy (strictly two islands linked by a causeway), which has 3 ferry routes from Orkney mainland, and deserves several days on its own. Time which any tour is just not going to give you. Only one of those routes is a vehicle ferry as even Hoy with its small population has surprisingly good public transport.
Three days is just scratching the surface, the longer the time you have there the better.
The Churchill barriers- the North South road were not primarily developed as a civilian road, but as part of the National defences due to the Grand Fleet being anchored in Scapa Flow, they actually remained under Royal Navy Control until as recently as 2011.
In fact one of several routes to Orkney is to fly on the Public Service Obligation route from Aberdeen to Wick, then take the Pentland ferries route from Gills Bay to St Margarets Hope, then across the barriers to Kirkwall.
I highly encourage even the shortest visit to include one of the outer isles flights. All the inhabited islands can be done as day trips, one way by air, the other by ferry.
The flights are as much for locals and school traffic as they are for tourist sightseeing.
Something you are very unlikely to get on an organised tour due to the tiny size of the aircraft.
The ultimate island adventure on Orkney is the unique island of North Ronaldsay- fly one way, twice weekly ferry back. In October that would be good luck as the ferry is frequently cancelled or retimed due to poor sea conditions.