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I would do the first part, but would head to the Camino Francés after the concert, as I think that the Francés is better for a first timer than the Madrid.
To make it easy on yourself I would probably start in León. You can easily arrive in Santiago in the time that you have available without...
Ivar's service is great, and I have used it, but it's best when you are mailing from within Spain. In SJPdP I recommend using the service of Express Bourricot. They make it super easy, and there's no worries about cross border mail service.
https://www.expressbourricot.com/luggage-transport/
Do you have to start the same day that you arrive in Santiago/Sarria? If you have time in your schedule I strongly urge you to slow down and spend the night in Sarria before you start.
Here's more information about this promotion.
https://partner.booking.com/en-us/help/reservations/manage/what-know-about-our-free-taxi-promotion
If they don't require a credit card number I might go ahead and book the free transfer. Worst case scenario would be the car doesn't show up and...
I've been offered discount transportation from my airport to the hotel from booking.com, but never free. I'd check into the provider - is there a direct link to GETTING TRAVEL?
Click on the Rome2Rio link in post #2 - it will tell you how long the different transportation options take, and you can click through to the provider. Also, make sure that you spell San Sebastián correctly. There is an e in it. And its name in Basque is Donostia.
Rome2Rio.com says that the train is the best.
https://www.rome2rio.com/map/Madrid/Donostia-San-Sebasti%C3%A1n
You can buy tickets from Renfe.
https://venta.renfe.com/vol/buscarTrenEnlaces.do?c=_Elq8
Although Ivar's service is wonderful, I use Express Bourricot when sending my extra luggage to Santiago from St Jean Pied de Port. The cost is €70, and the process is much easier than dragging your luggage to the post office to be shipped. You just have to go to Express Bourricot's office...
There are several choices. Biarritz airport is the closest. Many people fly into Madrid or Paris and take a train and/or bus to SJPdP. The Olympics and Paralympics are in Paris this summer, so that could affect transportation.
A "travel to bayonne/biarritz/sjpp" tag has been added to the top...
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