Might be a tad to late here, but Dean gave you some great advice. I like to also add to the plate some suggestions. Key West is highly noted for there restaurants & shopping on Duval St. besides the Duval crawl. Definitely stop by Fast Buck Freddie's for shopping. For breakfast go to Blue Heaven, very funky & is located in the Bahaman Village on the corner of Petronia & Thomas St's or Pepe's Cafe located at 806 Caroline St. Lunch at Alonzo's Oyster Bar located at 700 Front St. at A&B Lobster House, outside seating & a great view of the gulf, Turtle Kraals, also a great view & is located at Lands End Village at Key West Bight across from the Half Shell Raw Bar, a locals favorite or B.O.'s Fish Wagon for a great fish sandwich or Louie's Backyard, located at 700 Waddell St. for a view of the ocean & a little bit expensive. Stop by the Schooner Wharf Bar for a sandwich & some great music by Mike McCloud Key West Bight at Historic Seaport & for evening dining there is El Siboney, a locals favorite & great Cuban food & not bad on the billfold, located at 900 Catherine St., or El Meson de Pepe located at Mallory Square for Cuban food & great Latino music, 7 Fish located at 632 Olivia St. or Marquesa Cafe, probably need reservations for both or if you want romance & great French dining I would highly recommend Cafe De Artistes at 1007 Simonton St. & make reservations weell ahead. After all of that, stop by the Blond Giraffe at 629 Duval for the best key lime pie in the world.

Take the Old Town Trolley or the Conch Tour Train (recommended)for a great view & history of the island. This way you & your wife can see some of the attractions that might be of interest to y'all such as the Ernest Hemingway House, located at 907 White Head St., Harry Truman Little White House, located at the Truman Annex, Key West Light House or Aquarium, Mel Fisher Museum, Flager Station, take a glass bottom boat tour, historic & haunted ghost tours & make sure you stop by Fast Buck Freddie's for some great shopping. Don't forget about Fort Zachary Taylor beach also, might cost you a couple of dollars to get in but worth it. The last thing is Mallory Square for sunset activities or you might consider a sunset cruise on board the Floriadays docked at the Hyatt resort for a very romantic evening. :D