Possible Clues:

• Italian city named in sea-trip
• Italian city in Tuscany
• St. Catherine's city
• Italian town with a biannual horse race
• Odd stiles near Tuscan city
• College near Albany, N.Y
• Tuscan city with a famous horse race
• Nuyorican music legend Tito
• City served by Galileo Airport
• Italian city known for its Chianti