My recommendations for Key West, FL

• https://blueheavenkw.com — go for brunch and jazz, this used to be a boxing ring where Hemingway refereed matches- eat the best key lime pie of your life! If you happen to go when they are closed (in September, annually) go to Salute! on the Beach for the exact same pie.
• http://www.louiesbackyard.com — this is your fancy dinner date destination, for a truly exceptional experience, go around sunset and ask if you can sit upstairs on the balcony.
• https://www.bagatellekeywest.com go for brunch or lunch or dinner, their Eggs Benedict was amaaaazing and their tuna with cold noodles was one of the best tuna dishes I’ve had in years.
• https://moondogcafe.com for brunch or lunch or coffee — get a cream cheese & guava danish and an iced cafe con leche. Their “feel good bowl” will cure any vacation-related ails you may have.
• https://firstflightkw.com for a beer tasting flight (or a banana daiquiri) and some brisket mac n cheese. I haven’t tried their fried Pb&j served with ice cream yet, but it’s on my list.
• Cuban Coffee Queen — multiple locations, we like the downtown one best, but the waterfront has a very instagrammable “key west” sign.
• https://rodriguezcigarskeywest.com — they have an educational tour which includes a lesson in cigar rolling, super worth the time.
• https://www.oceankey.com/key-west-fl-spaterre/ — get a massage or facial and you get a free pool pass- and their pool bar is excellent!
• https://www.hemingwayhome.com to visit Hemingway’s house and polydactyl cats.
• https://keywestbutterfly.com — surprisingly magical.
• https://www.keywestpottery.com — fun and unique pottery.
• Fort Zachary Taylor has the best beach. Spend a morning or afternoon, there are sandwiches and drinks available on site.
• If you do find yourself on Duval Street— pop into Wicked Lick for ice cream (their peanut butter ice cream with mixed berry compote is my fave), enjoy Guild Hall Gallery, and step inside St. Paul’s Church.
• Go for a kayak tour in the mangroves- sunset is especially magical out on the water.
• Rent a scooter! Or a bike! Or a golf cart! Google for this- or ask your hotel to arrange a drop off.