We were in town on our next to last port on a Western Caribbean cruise. We were in Key West last year for the trolley tour and thought about staying on the ship since we were also familiar with KW from past family trips.
I knew we would learn something new so we booked the trolley onboard "Empress of the Seas." I booked the excursion through the RCCL Shore Excursions desk and was amazed at the price difference between buying onboard and the price charged on shore: $13 cheaper on board! Typically, ship excursions are more expensive.
We skipped the line at the trolley since we got a sticker on the pier which allowed us to board directly. We left at 9:00 a.m. with Bob, our driver/guide. He was knowledgeable about the city; I took extensive notes. Bob taught us about the major industries that rose and fell (cigar, Flagler railroad, shrimp, salt ponds, treasure hunting) plus a good orientation to other spots and a lot of history. We had lots of time for independent exploring after the 90-minue tour. Our ship didn't leave until 5:00 p.m.
After the tour ended, we made a point to stop at the Key West Lighthouse which he pointed out on the tour and to climb the 88 steps to the top. Afterwards, we visited the lighthouse keeper's cottage on site. This is one of the benefits of going on a tour: get an orientation and then go back to stops that interest you.
The 90-minute tour and gratuity (DON'T FORGET to tip your driver) was money well spent. Every driver has his or her own style of narration. We liked Bob's historical perspective.