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Ideas for a vacation in late October

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We (my husband, my son (age 16) and myself are looking for ideas for a beach holiday with interesting outing possibilities (e.g. visiting historical or nature sites, towns or cities with markets, clothing shopping, good restaurants) in late Oct. for about 7-10 days. We are based in Europe.
All three of us like beach vacations but we can't sit on the beach everyday and like to go see interesting things in the area. None of us really like areas whose tastes are geared towards mass tourism (esp. not when it comes to the restaurants). Since we are traveling with our 16 yr old, secluded single/honeymoon beaches/hotel resorts don't come in question.
Our budget is also limited to about $4,000.
Places we are thinking about:
Cyprus (con: $$$), somewhere in the Caribbean (con: hurricane season), Crete (con: end of season?), Canary Islands (con: mass tourism?)....

Can anyone help us out with some ideas?