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Interested in folks' answers. I never used earbuds and music on the Camino Frances, but on long days on the Via Francigena, where all the end towns are at the top of high hills, I found it energized me to groove to Motown hits or dance songs. Just enough to conquer the slog...
Why not split the difference and go in mid-May if you can? One thing to consider is that the Meseta is just spectacular in late May and early June, when the poppies are in flower.
My favorite hat is also a Tilley. It stood me well for 3 Camino trips. A little warm on hot days, but not a deal breaker. I inherited mine from my father. For those worried about current quality, you could check eBay for preworn ones.
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