Funny. I have a friend who retired in his mid 50s and moved to Malaga Spain to live the ex pat life. He and his wife are able to fly cheaply all over Europe and are traveling a ton. They have been twice and are in love with the Madeira. Mountains, gorgeous beaches and coastlines. Friendly people and great food. Says it's really inexpensive too. 4 star hotels for 100 us. They stayed the first time in and around Funchal. Ventured out the second trip and stayed in smaller towns around the island. Said language barrier gets tough the more rural you get.
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