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12. Philadelphia
The birthplace of our constitution is a destination rich with history. From the Liberty Bell to Independence Hall, to the bustling Italian Market to hip South Street, there's a diverse array of historical, cultural, and entertainment options (many of which offer senior discounts on admission). Or you could just head to 9th and Passyunk Streets and do a taste test to find out whether Pat's or Geno's cheesesteak is truly the best.