Here is a list of our personal favorite must-see and must-do experiences we’ve gathered from decades of Key West living — plus we’ve added plenty of new and more recent additions as well. And as we find more worthy of our list, we’ll certainly update accordingly so you are always in the know. We know that great food and dining, fun experiences, and maybe even a few cold ones, are all key to a perfectly fulfilling Key West vacation – and we want to you to have the best time possible. So you can always count on the following list as an honest, non-paid promotion of what we truly think are your best options in town.

Things To Do

  • Mallory Square at Sunset – Make sure you get there early to walk around, have some snacks or a drink, shop for some cool local art and of course, TO GET A GOOD SEAT!
  • Key West Aquarium – Not just any aquarium, I am a lover of the seas and this one lets you pet sharks, watch them feed and pet sting rays!
  • Dry Totugas – Beautiful trip, but please make sure you only go during the hotter months of the year, it’s a waste to go when the water is still too cold for swimming.
  • Little White House – Did you know how much the old time President’s loved Key West?
  • Snorkeling – Fury or Sunset WaterSports
  • A Show 801 Bourbon – Not for every trip!
  • Red Barn Theatre – Has local shows in a back alley theatre, very cool experience.
  • Esky Rods – Best custom rods around (and reasonable) the locals ACTUALLY use! Great gift.
  • Key West Moped Scooter Rentals – Visit my “very special” Uncle Richard, not for the easily offended.
  • Cowboy Cowgirl Fishing Charters – Captain Mark Baumgarten
  • Fort Zachary Taylor Beach & State Park – Best beach in town, it is private so you will have to pay a few dollars to get in, but you may also visit the Fort while there. The beach is rocky so we recommend getting some water shoes (At Shaddow & Fish of course!) but also although it is right off of Duval, do not plan on walking there. There is a VERY LONG winding, hot road to get from the gate to the beach. Bike, cab or drive in. The water could not be more refreshing.
  • Key West Escape Room – The one downtown off of Simonton, WOW would I recommend getting a package for multiple because these are unlike any escape room you’ve done before.
  • Southern Most Point & Mr Eddie’s Coconuts – Wait in line in style for your SMP photo by stopping next door to the coconut cart where Mr. Eddie will drill into a fresh coconut for you to sip on while waiting. Makes for a better picture too!

Restaurants, Sweets & Treats

  • Banana Café – Great breakfast.
  • Latitudes Sunset Key – Romantic dinner or fancy brunch, or a great place to propose 🙂
  • El Siboney – Our most popular cuban restaurant; Must go.
  • Croissants De France – Great breakfast.
  • Santiago’s Bodega – My favorite restaurant on the island, tapas style and out of this world! If you go for HH they have a $5 menu, mix those with some regular tapas and you’ll eat like a king! I also love their red sangria.
  • Alonzo’s – Go for Happy Hour!!!
  • Bo’s Fish Wagon – You are not going to get a better fish sandwich IMO. Their Key Lime Honey Mustard is out of this world! This is really an old time hole in the wall but you MUST experience BO’s.
  • The Commodore – Excellent steak dinner, indoor seating only though.
  • Date & Thyme – Healthy and vegan, but anyone can enjoy. Closes at 4pm, would recommend for lunch or juices.
  • Caroline’s – Just go here to drink a beer, have some conch fritters and people watch… now you’re a local.
  • Blue Heaven – Good things are worth waiting for!
  • Pepe’s – Pancakes & coffee here are a must.
  • Kims Cuban – Best cheese bread or bacon, egg & cheese on the island (get it with mayo and it will change your life).
  • 5 Brothers – Old town favorite for morning breakfast to go.
  • Tavern & Town – (“Talk of the town” as my mom used to call it) Must take advantage of their happy hours and go to dine like a local, the food is fantastic.
  • Louie’s Backyard – A view like no other, food is delicious.
  • Origami – Locals dine here. Simple and great sushi (the gyoza and tempura app are incredible too!)
  • Sunset Pier – I love the fish sandwich here.
  • Flamingo Crossing – I have been adoring their homemade ice cream and milkshakes my entire life. It does not get better than their ice cream. Cookies & Cream here is to die for.
  • Better Than Sex – A dessert experience like no other. Get a glass of wine with a chocolate rimmed glass.
  • Matthessen’s – Biggest and best chocolate chip cookies, get them fresh out of the oven!

Bar Hopping

  • The Rum Bar – Great place on the quiet end of Duval for a nice drink and some conversation.
  • The Porch – Excellent place for a classy cocktail for a casual evening or priot to heading out for a night on the town. Either way – you MUST stop here! It’s located inside an old Key West mansion.
  • Virgillios – Martini Monday here is THE BEST!! The Key Lime or Espresso Martini are quench worthy.
  • Flying Monkeys – This was our favorite place growing up
  • Fat Tuesday’s – Music is more rap/hip hop/top 40’s
  • Ricks Upstairs – Top 40’s
  • Ricks Downstairs (Dirty Harry’s) – Live Band
  • Irish Kevin’s – Live Band (always excellent music) and sneak up top to the private balcony area (theres another bar up there where the locals go!)
  • The Green Room – Small bar but a great hole in the wall