48 Hours in the Key West

Captain Tony's Saloon, Key West, Florida
Captain Tony’s Saloon, Key West, Florida

I get asked all of the time what is not to be missed while in Key West and I always reply with something like, that all depends on what your interests are. For people like myself, visiting a few museums is a must while for others that would be snoozeville. After pondering this question for awhile, I have put together what I consider the best of the best when it comes to history, art, dining, watersports, etc. This way visitors can look at the list and pick what to do from the categories listed that appeal to them.

Classic Harbor Line Key West Schooner America 2.0 Sunset Sail
Classic Harbor Line Key West Schooner America 2.0 Sunset Sail


  1. Ernest Hemingway Home and Museum – 907 Whitehead Street
  2. Fort East Martello Museum and Gardens – 3501 S Roosevelt Boulevard
  3. Key West Aquarium – 1 Whitehead Street
  4. Key West Butterfly and Nature Conservatory – 1316 Duval Street
  5. Key West Shipwreck Historeum – 1 Whitehead Street
  6. Lighthouse and Keepers Quarters Museum – 938 Whitehead Street
  7. Mel Fisher Maritime Museum – 200 Greene Street
  8. Museum of Art and History at the Custom House – 281 Front Street
  9. Oldest House and Gardens – 322 Duval Street
  10. Truman LittleWhite House – 111 Front Street
Island Genn With A Nice Key West Dolphin (mahi), fishing with Dream Catcher Charters.

Art Galleries

  1. Alan S. Maltz Gallery – 1210 Duval St.
  2. Audubon House & Gallery – 205 Whitehead St.
  3. Frangipani Gallery – 1102 Dual St.
  4. Gallery on Greene –  606 Greene St.
  5. Gingerbread Square Gallery –  1207 Duval St.
  6. Guild Hall Gallery –  614 Duval St.
  7. Island Style Gallery –  620 Duval St.
  8. Lucky Street Gallery – 1130 Duval St.
  9. Peter Lik – 519 Duval St.
  10. Wyland Galleries of Key West – 623 Duval St.; 102 Duval St.
Pizza chef showing off one of his creations at Roostica Wood-fire Pizzeria


  1. Banana Cafe – 1215 Duval St.
  2. Croissants de France – 816 Duval St.
  3. Latitude’s at Sunset Key – 245 Front St. (breakfast, lunch or dinner)
  4. Hogfish Bar & Grill – 6810 Front St.
    (lunch or casual dinner)
  5. Bagatelle – 6505, 115 Duval St.
    (lunch or dinner)
  6. Salute – 1000 Atlantic Blvd.
    (lunch of dinner)
  7. El Meson de Pepe’s – 410 Wall St.
  8. Origami – 1075 Duval St.
  9. Seven Fish – 921 Truman Ave.
  10. The Commodore – 700 Front St.
Wyland Art Gallery Key West
The front of the Wyland Art Gallery in Key West, Florida


  1. Virgilio’s – 524 Duval St.
  2. Smokin’ Tuna – 4 Charles St.
  3. Louie’s Afterdeck – 700 Waddell St.
  4. Green Parrot – 601 Whitehead St.
  5. Sloppy Joe’s – 201 Duval St.
  6. Capt. Tony’s – 428 Greene St.
  7. Irish Kevin’s – 211 Duval St.
  8. The Porch – 429 Caroline St.
  9. Agave 308 – 308 Front St.
  10. The Rum Bar – 1115 Duval St.
Hemingway Home
Ernest Hemingway Home and Museum, Key West, Florida


  1. Fishing – Whether you prefer inshore or offshore, no trip to Key West is complete without spending some time on the water.
  2. Snorkeling – The Florida Keys have the only living coral reef in the northern hemisphere, so why not experience the magic of this amazing array of corals and tropical fish.
  3. Dry Tortugas – This remote National Park can only be gotten to by boat or seaplane. Enjoy touring the Civil War Fort Jefferson, snorkeling the pristine waters, bird watching, or just being off the grid for a few hours while enjoying the gorgeous scenery.
  4. Beach – This State Park is not only beautiful, but it also has so many things to do. From snorkeling, nature hikes, swimming, and sunning
    Filet Mignon at the A&B Lobster House

    to exploring the Civil War era fort.

  5. Sailing / Sunset Sailing – Sail the calm backcountry waters during the day or at night and watch the gorgeous Key West sunset from the water.
  6. Watersports – From guided wave runner tours around the island to all day water sports packages that include banana boat rides, parasailing, kayaking, and more. The choices here seem endless!
  7. Biking – Bike rentals are available at many hotels and shops. And there is no better way to get around the island than via bike.
  8. Old Town Trolley – Take a narrated tour around the island. The best
    Enjoying a drink on a rainy Key West day.

    thing about this option is that you can hop on and off the tour at different points of interest. A great way to get the lay of the land and figure out how you want to plan out the rest of your visit.

  9. Biplane Tours – Check out the island from above where you can experience the beauty from an entirely different altitude.
  10. Kayaking & Paddle Boarding – This is becoming a very popular activity. Choose from rentals or tours.

So hopefully, you have found some fun ideas on how you should spend at least some of your time in Key West! To see what is happening on Key West during your visit, check out our Key West Events Calendar to see other upcoming special events. For more information about the fun side of Key West… things to do and see in our island city, go to our Key West Web Site.

Feel free to Email Me if you have any questions about Key West!!

Island Genn
Key West Concierge

About the author: Island Genn

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