I would take Cape Air from RSW, my fiance (my girlfriend at the time) and I flew down to Key West for the day since we where staying the week with my grandparents in Naples. This was a surprise for her! We took the early flight out of RSW and had about 6 people on the flight, it took about 50min to get to EYW. We got in early and walked from the airport to downtown (don't recommend it unless you really like to exercise! lol) and took her around the island and showed her different places since it was my 3erd time down there. Before lunch I took her to the light house and we made our way up to the top and that's where I gave her the ring! =) We then ate at Margarita Ville, after doing some shopping for the family we ended up taking a cab back to the airport which was expensive but worth it lol. We took the last flight out and enjoyed a beautiful sunset. On the way back to RSW we where the only ones on the 402 to it was like having your own personal plane and pilot despite the fact I wanted to be the one flying. Sorry, I like telling that story! The Cape Air employees are awesome, they where all friendly and very helpful. I have done the drive, it is not bad....but I would never do it over. Have fun in Key West! PM me if you need help finding things to do.