Take your pick of dozens of uniquely decorated guest houses and B&Bs, many starting out as exclusively LGBT-Q compounds but now hetero-friendly "adults only," refuges like the two acres of gardens and pools at Simonton Court.
After breakfast at Frenchie's Cafe, stroll over to the Hemingway House and Museum where Hemingway did some of his best work.
Meander to the old straw market at Bahama Village and lunch at Blue Heaven or Santiago's Bodega. Then spend the afternoon browsing shops on Duval and around Mallory Square where you'll find boutiques selling unique tropical fashions, hand-crafted sandals, swimwear, hand-rolled cigars and gourmet food products.
Drop in Key West Island Books to pick up novels by local writers (like Hemingway) and check to see if any authors' talks are scheduled. And don't miss Gingerbread Square Gallery on lower Duval Street, a gallery established in the 1970s by one of the nation's first openly gay mayor.
To cap off the evening, take the launch to dine at Latitudes on exclusive Sunset Key or a wine-and-cheese sunset cruise. Or go to the Tennessee Williams Theater on the community college campus if something is in production.