Ooooooh Key West! One of my favorite ports! Been there twice on the Magic and loooove it like no other.
Both times we docked there we were on the Navy pier (not the main cruise pier that dumps out into Mallory Square area). When the ships dock at the Navy pier they have trolleys there when you step off to haul you into town. The drop off/pick up point is right there in the thick of everything. Door to door service. It's nice plus you get a little bit of stuff to see coming and going.
I'm trying to remember which half of the day y'all are getting on the Oct 1 Wonder. Tracey & I *may* still land on that sailing, too. ((He's getting ready to sell his boat so a lot rides on how much over payoff he ends up fetching for the thing.)) Do you recall your port times??? Is it the early one?
Anywhoo, first trip to Key West was a 12:30 all-ashore. We rented a golf cart thing and did some riding around before heading over to the airport. That's when we did the private sea plane tour. That was awesome. I booked it all by myself for Tracey's 40th birthday. I want to say the golf cart was like $99 and the sea plane tour (complete with 2 water landings & takeoffs) was around $595. We had 4 of us for the ride so I didn't feel like that was all that unreasonable. That trip when we passed the Southernmost Point on the way to the airport there was a bit of a lineup on the sidewalk for photo ops. On our way back the line was gone so we quickly parked and ran over to the thing. Worked out good.
The second trip to Key West was the early morning all-ashore. Again, we rented a golf cart ($99) and tooled around a bit. We scoped out some places we wanted to go so we knew where to walk to. Nothing was open that early so it was fun to quietly hum along just looking at the houses and soaking in the island's waking up time. After we returned the cart (parking is scarce along Duval) we strolled to the places we wanted to go. And I got to go shopping at the Lilly Pulitzer store for the first time....thus starting my obsession with all things Lilly.
If/when we get back via a cruise ship I'd like to do a jet ski tour. They look fun, last 2 hours, and circumnavigate the entire island. Not unreasonable on the cost especially if you catch the early time. I did some calculating on the early tour time. Tracey & I could make the tour, return to the ship to refresh, then still have plenty of time to head out and grab a chocolate dipped keylime pie on-a-stick from Kermit's as well as hit up a few of our favorite shops before all-aboard.
Ps. The Southernmost Point is no longer the actual Southernmost Point. It's the Southernmost
naturally occurring point. The island was actually extended out in length when they dredged up the ship channel and deposited all that material into "new" land.