Possible Clues:

• You and I to descend on mostly pebbly seaside resort
• "I'm Henery the Eighth, I Am" composer R.P.
• "In Treatment" psychologist Paul
• ''I'm Henery the Eighth, I Am'' composer R.P.
• _____, Ontario (sounds like Reston, Manitoba)
• Boston suburb
• Town on sea that provided good wine
• "I'm Henry the Eighth I Am" composer R.P.
• ''I'm Henry the Eighth I Am'' composer R.P.