Hey 308,
Just a little more information on the ferry to KW. It is called the Key West Express and they have boats that sail out of Miami, Marco Island, and Ft. Myers Beach. The cost right now to go over from FM is $129 round trip. The price used to come down when the season ended, but that has not happened this year. I guess the price of gas has hit them also! From FM it is about a little less than four hours over to KW. Great ride, but you must get there early to get a good seat. Get there late, and you are riding in a seat on the top deck with no protection from the sun and no air conditioning. The key to getting a good seat is to buy your tickets and pick them up the day before your trip. That way, you are not waiting in a long line to do so and therefore eliminating any chance of having a good seat selection.
This is not a bad way to go over, but remember, if it is just you and your gf. So you have to ask yourself, can you look her in the face for almost four hours and just talk? If not, they do have closed circuit tv, take a book, or take a couple friends to bs with.
They do have two fenced parking lots for cars, but I don't know that I would be comfortable parking any of my Vettes there for multiple days. Just me I guess.
If you decide to do KW, I would recommend the Key West Innkeepers Association. They handle booking to most of the quality B&Bs and did a great job for my wife and I a few months ago. We stayed at a B&B called Westwinds. Very nice. We had a small cabin that opened up to one, of two pools. There grounds are small but very secluded with the tropical vegetation they have planted. Breakfast is a continental breakfast that is served pool side every morning. Parking may be an issue here. Since we went over by boat, we did not have a car, but I don't recall them having a bunch of parking. The Innkeepers association can help you with this.
There is a high rise (couple stories) parking garage just a block from where the KW Express docks. We were there during the last couple weeks of the season and the garage had plenty of open parking.
OR, have you every thought of just going on a road trip and see many locations. As an example, put the gf in the car and head south. Sarasota has a number of interesting things to visit. If you are into museum style art, then the Ringling facility is a must visit. Then you can travel down toward Ft. Myers. but make sure you stop at Fisherman's Village in Punta Gorda. Beautiful view for lunch and some great little shops to satisfy the gf for an hour or two. Then go south to Sanibel/Captiva. Great laid back location for beach, shelling, etc. Very family oriented, which means not a ton of spring break type partying. Sunsets at the Mucky Duck are fabulous, and dinner at the Bubble Room is a must. Then you can venture down to Marco Island. If you planned something like this, you could also coordinate with the members of this board in each area to have a little group lunch or dinner at various spots along the way.
Unless, this is going to be a romantic voyage with the gf and then this might not be what she has in mind.
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Anyway, good luck with whatever you come up with. If I can be of help here in Ft. Myers, just let me know.
Rich