We did the dinner train on Saturday night. It left the station at 6:30. We chose the candlelight option. There was also a cabaret option and a murder mystery option. All the meals were the same selections. It was ~2.5 hour ride. We got to see the sun set over the bay. Very enjoyable, romantic and relaxing.
Another night we went to The Beachwood Speakeasy (at the Astor's Mansion). It was a catered (appetizers) event with a cash bar. The entertainment was very enjoyable. They served alcoholic beverages in tea cups (remember it was depicting prohibition time). You needed a password to get in. You were given the password by the butler/car attendant who was wearing a long tail tuxedo. You were seated at a table of 8. It was a lot of fun and we would highly recommend it.
One other evening we took the candlelight tour of Belcourt Castle. That was very interesting. Part of the castle is a "museum" and the other part (which was off limits to us) is where the owners live.
Fort Adams gave us a very informative tour, as did Kingscote Mansion.
Cliff Walk is always enjoyable. We started out by 1st Beach and made our way to the other end. Near the last mile, it got a bit difficult walking. It took us 2 hours and we walked back on the road because we were pressed for time.
One day we flew a kite at the park on Ocean Drive. That was a lot of fun. Many people around enjoying the scenery.