What do you like to do? Do you want B&B/hotel or a cottage. One spot or tour around?

I'm looking to stay in a B&B or hotel in a central spot & then travel around the islands

There are a few hotel and B&B suggestions within this forum - have a read through and see if there's anything that suits you. If you are taking your dogs you might be better off self-catering. Ferries to other islands mostly go from Kirkwall so that might influence you a bit.

Will you have a car? Public transport is not that great so if you don't have a car you'd need to use a tour company to get the best out of your visit.

Must-sees are Maes Howe, Skara Brae, Tomb of the Eagles, The Italian Chapel - again, there is plenty of info on these within this forum.

Thanks for the advice.

I've found somewhere to stay on South Ronaldsay (dog friendly is a huge priority and I've found somewhere that genuinely welcomes dogs).

My plan is to spend a lot of time chilling / walking and have a few excursions to the recommended sights over the two weeks.

I will need to use a taxi service for my excursions as I don't drive – any advice on how practical my plans are would be more than welcome.

As you will be in South Ronaldsay (without a car?)

I really recommend that you book a couple of tours.

Try Wildabout - they are very flexible.

There is a good bus service from South Ronaldsay. I think you will enjoy Orkney no matter were you stay. It won't be much of a holiday travelling with two dogs though that's hard work. Have a great time we are still in Orkney we stayed five nights at Houton Bay Lodge in Orphir Mainland Orkney scotland for five nights it is on the Scapa Flow and has a private beach with seals on it. That place is great it has everything and food is excellent they have a new chef from Spain who worked in France before so his food is very Mediterranean using all of Orkney's fresh ingredients. They don't take dogs though. But you could go for lunch there on your own. Have a great trip. I think you would be better off going self catering also.