Off Montgomery:

South of Ocean Beach Pier 500ft - Offshore transition

Point Loma lighthouse 800ft

Up the channel, North Island NAS - Bay transition

Over the Coronado Bridge, San Diego cityscape 1500ft

Over Lindbergh - Taxiway Delta transition 1500ft

Exit the Bravo to the north, then back over to Montgomery.
How it's done:
Offshore transition - Call Lindbergh tower 1 mile north of Crystal Pier (Pacific Beach). Tower will clear you at or below 500 feet. Report 1-2 miles south of Ocean Beach Pier.
Bay Transition - Call North Island tower south off Ocean Beach Pier. Tower will clear you through the harbor. Don't overfly naval ships. Tower will hand you back to Lindbergh tower at Coronado bridge.
Delta Transition over Lindbergh - Call Lindbergh tower south of Coronado bridge. Tower will clear you to fly over delta taxiway direct to Mission bay VOR at 1500 MSL. Expect frequency change at Mission Bay VOR.
Real world video clip with comms:
https://www.youtube.com/watch?v=ryDPNdoOsE8
Nick