- Go to Mallory Square for sunset
- Snorkel, kayak, jetski
- Tour the Hemingway House
- Fort Zachary Taylor State Park
- Tour Truman's Little White House
- Bar hop on Duval Street
- Shop Old Town
Must try: Cuban coffee
- Key West Cuban Coffee
- Cuban Coffee Queen
- Ana's Cafe Cubano
- Blue Heaven
- La Grignote
- Date & Thyme
- The Koffie House
Must try: conch fritters, conch chowder, Cuban food, any fresh-caught fish
- Marlin Cafe
- Mr. Z's
- Frita's Cuban Burgers (amazing Cuban sandwiches)
- Kaya Island Eats
- Hot Tin Roof
- FIsherman's Cafe
- 5 Brother's Grocery & Sandwich Shop
- El Siboney
Must try: Key lime pie, Cuban pastries
- Better Than Sex
- Glazed Donuts
- Kermit's Key Lime Pie Shop
Must try: Key West rum, Cuban-rolled cigars, and getting on stage at Irish Kevins
- Irish Kevins
- Sloppy Joe's
- Green Parrot Bar
- Bobby's Monkey Bar
- Willy T's
- Hog's Breath Saloon
- Smallest Bar
- Dante's Key West Pool Bar
- First Flight Island Restaurant & Brewery
- Key West First Legal Rum Distillery
- Southernmost Pint Brewpub
- The Waterfront Brewery
Key Largo: Harriette's (best biscuits and gravy) Mrs. Mac's Kitchen
Tavernier: Blond Giraffe Key Lime Pie Factory (best Key Lime pie in the Keys) Cafe Moka, Gardenia's Bistro, KRUST
Islamorada: Bad Boy Burrito, Twisted Shrimp (a favorite), Islamorada Brewery & Distillery, Florida Keys Brewing Co. Check out Robbie's to feed some tarpon!