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Portugal in May: Hiking & 1-2 days on beach

My husband and I want to travel to Portugal in mid-May and hike part of the Rota Vicentina and then go to one of the beaches near the southern end of it for 1-2 days.

I wanted to see if anybody had suggestions about good places to start the hike (and how to get there from Lisbon), and beaches to go to that wouldn't be too far from the end or too far from a good end point. We'd like to hike for 3 days.

Also, if we hike in mid-May on this trail, is it hard to just stop when we want and find a place to stay or will we need reservations? Any thoughts on traveling in May in this area would be appreciated as well.

We would probably end our trip with a full day in Lisbon.

Thanks
Amy

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