I’d set about a trip from Oban. Get an Island Hopper ticket off Calmac.
Barra is fantastic, camp on the beach at Eoligarry. On South Uist stay at the Gatliff Trust hostel at Howmore. The beaches on S. Uist are amazing.
Benbecula is a bit dreary and dominated by the MoD, there is a good Co-Op on the “main” road though…
North Uist is OK but the jewel in Berneray – again stay at the Gatliff Trust hostel. It’s fantastic and right on the beach. We watched otters from the hostel door step.
Harris is great with brilliant walking (Clisham is the highets peak in the Hebrides and reaches Corbett status) and the southern end around Tarbert has some fab beaches.
At this point I’d stick in terms of where to stay. Head to Lewis for the Callanish stones. If you do want to head further north there’s a great beach and campsite at An Cnip. However Lewis is the home of the “Wee Frees” and is a bit dour. Stornoway is not a social town.
From Tarbert you can get the ferry back to Uig on Skye and enjoy the delights of the Sligachan Hotel!
I love it up there!
Chris