20 Things to Do in Key West for the First-Timer

Key West has an ambiance that you cannot fully describe to someone that has never been. It has a Caribbean laid-back feel without ever leaving the United States. It is a citland; a blend of city and island. It possesses beautiful architecture, serene gardens, delicious food and a wild bar scene with the added benefit of wavering palm trees, soft sand and breathtaking sunsets.

Many have been enchanted and inspired by the unique vibe of Key West such as Ernest Hemingway, Tennessee Williams, Robert Frost and Jimmy Buffet. Visitors are there to have a good time and are jovial to the core. Residents are known for their “anything goes” attitude and have adopted the One Human Family motto:

We are all like fingers on a hand… we are all different and unique. We are all of equal value. We are all created to work together. And although we appear to be separate, we are all linked to and apart of each other.

The combination of acceptance, lack of judgement and easy pace, creates a euphoric feeling of wanting to leave your inhibitions at the entrance of the Seven Mile Bridge and let your freak flag fly!

In no particular order, here are 20 Key West things to do for any first-time visitor:

      1. Eat Tacos a Garbo’s Grill Food Truck. The owners of this establishment caught the Key’s Disease and moved down here to open their own restaurant, well more like a 6 x 8 food cart. The food is mouthwatering! Try to go between the usual eating times because there is usually a line.
        Key West Things to Do
        Garbo’s Fish Tacos
      2. Listen to the antics of Kevin at Irish Kevin’s Bar and don’t forget to look up at the Jameson chandelier.
        Key West Things to Do
        Irish Kevin’s
      3. Pet a six-toed cat, see a urinal turned water fountain and walk over Hemingway’s last penny at the Ernest Hemingway House. Situated in Old Town Key West, the tour gives an insider a look into his personal life and the notable mark he left on the literary world.
        Key West Things to Do
        Hemingway Cat
        Key West Things to Do
        Hemingway House
      4. Soak in a Sunset at Mallory Point. Walking hand in hand along the water, watching the boats glide by as the sun slipped away was one of my favorite moments while visiting Key West.
        Key West Things to Do
        Sunset at Mallory Square
      5. Bar hop and people watch on Duval Street. You must make your way down Duval and embrace your wild side! Make sure to at least visit Green Parrot Bar, Sloppy Joe’s and the Garden of Eden.
        Key West Things to Do
        Sloppy Joe’s
      6. Listen to one of the many talented live bands at Hog’s Breath Saloon.
        Key West Things to Do
        Hog’s Breath
      7. Take advantage of Happy Hour. Most bars and restaurants offer happy hour deals on food and drinks.
      8. Eat Breakfast at Pepe’s Cafe, the oldest joint in Key West.
        Key West Things to Do
        Pepe’s Cafe
      9. Take a picture at the Southernmost Point. Get there early or late or on a day when the cruise ships are not there. We couldn’t believe the line there was to take a picture with a buoy! We didn’t wait, we just sort of snuck in between and with other people.
        Key West Things to Do
        Southernmost Point in the U.S.
      10. Walk around the Secret Garden of Martello Tower. It’s free and it’s gorgeous!
        Key West Things to Do
        Martello Tower Gardens
        Key West Things to Do
        Martello Tower Gardens
      11. Hang out on Smathers Beach. Walking around town or even most of Key West, you’ll think they have no beaches at all. They are the least exciting thing the island has to offer. With that being said, Smathers Beach offers a long stretch of sand to enjoy a walk on the beach, volleyball or a picnic.
        Key West Things to Do
        Smather’s Beach
      12. Have a drink, dance and listen to live music at sunset pier at sunset. The drinks are a bit pricey, but worth it for the entertaining atmosphere.
        Key West Things to Do
        Sunset Pier
      13. Check out the floating community off of S. Roosevelt Boulevard, reminiscent of the old houseboat row. It’s a collection of colorful houseboats with a whole lot of character.Key West Things to Do
      14. Eat free samples at the Kermit’s Key West Key Lime Shoppe. Get your munch on with free samples of key lime jelly beans, taffy, cookies and salsa.
        Key West Things to Do
        Kermit’s Key Lime Pie Shoppe
      15. Try a few craft beers at Waterfront Brewery. Makes my mouth water just looking at that picture!
        Key West Things to Do
        Waterfront Brewery
      16. Stroll along the Harbor Walk at the Key West Historic Seaport. You’ll find fishing boats, fun bars, seafood restaurants, and waterfront shops.
        Key West Things to Do
        Harbor Walk
      17. Visit Lagerheads Beach Bar and don’t forget to wear your bathing suit!
        Key West Things to Do
      18. Browse the shops in Mallory Square.
        Key West Things to Do
        Mallory Square
      19. Take a picture at mile marker 0 to prove you made it to the end of the road where life slows down. US 1 stretches 2,369 miles from upper Maine to Key West.
        Key West Things to Do
        Mile Marker 0

     20. Visit the Key West City Cemetery and look for the gravestones that read, “I told you I was sick,” and “At least I know where he’s sleeping tonight.”

Key West Things to Do

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Plan Your Trip to Florida

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        • Hotels.com has a best rate guarantee program that allows you to price match up until 24 hours prior to arrival and its rewards program gives one free night for every 10 nights collected.


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Car Rental

        • Priceline is usually the cheapest for car rentals and has a best rate guarantee program as well.

Have you ever been to Key West? What’s your favorite thing to do? Tell us in the comments!

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Key West Things to Do

34 Responses

  1. gabi

    Great post with lots of insights. Liked it so much… and that chandelier is really a must-see!! Loved it.

  2. Kaylene Chadwell

    Key West sounds like a lot of fun! I went as a really young kid but don’t remember it much. The food and drinks look great too! And sunsets in Florida are always stunning!

    • Dang Travelers

      We had a blast exploring the island. The Hemingway House was interesting, the bars were insane and the people were all friendly!

  3. Nancy

    It’s been such a long time since we have been to Key West! Looks like there have been a few changes since we have been there. The two things I would love to do next time we get there are Martello Tower Gardens, looks fabulous and have breakfast at Pepe’s Cafe. If its been around this long must be good! Fish taco’s looked good too!

  4. Holly

    I’ve always wanted to go to Key West! And I love all of the pictures you included in this post. So colorful! Those tacos looked to die for. Great recommendations!

  5. ash

    Haven’t quite made it that far south yet, but some of these things are enticing me!

  6. Rebecca

    I haven’t been to Key West, but I’d sure like to visit a place that is slower. The tacos looks delicious and I would love to check out the Key Lime Pie Shoppe. The scenery looks lovely.

  7. travelling chingrita

    the weather and vibe is enough for me to head down, love food trucks and the seafood must be crazy awesome 🙂 nothing like sassy sayings in the cemetary

  8. Theresa

    Thanks for sharing your insights. Didn’t know some of the sites you presented. Taking a mental note for the next time I visit. My fave part of Key West though is the Key Lime pie at Blue Heaven.

  9. Alex Datsev

    Great suggestions, thank you! Haven’t been to Key West in year, so it is time to revisit…

  10. Debra Klein

    Love Key West. Kermits keylime the best. Pepes is a great place for breakfast. Green Parrot one of my favs. What’s not to love 🌴❤️

  11. Mike geer

    Mel Fishers maritime museum is also a cool stop. Lots of shipwreck gold and treasure. Tons of cool stuff to do

  12. Viki Holloway

    I have been to Key West a few times and I love it every time. (I am from Ohio). I plan on moving there when I retire.

  13. Mark Drais

    To start you need to understand what “Key’s Disease” really is before you use it in a positive way (Sorry). Second, you did mention a few things that does not involve drinking an alcoholic beverage. I live here and have done so for more then five years. Wife and I vacationed here for well over 18 + years before moving. Key West and, the Florida Keys have so much more to offer other then drinking and getting drunk. Why not talk about Fort Zack and the Civil War History? You did mention West Martello did you forget about East Martello and Robert The Doll? Look Sloppy Joes, Hog’s Breath, Irish Kevin’s and whatever other bar you mentioned plays a big part in this island for most. Yet its also has a long rich history, a wonderful art and music community that I wish writers would promote over the bar thing! Just sayin

    • Dang Travelers

      Living in the keys for 18+ years sounds great Mark. You’ve had much more time to explore than we did. We would love to come back and experience some of the things you’ve mentioned. We put together this list of fun things for the first-timer based on our visits.

  14. Carrie Murray

    Have you ever been to Nancy Forrester’s Secret Garden that is a parrot sanctuary? It is small, but a really neat place to spot by when in Key West. You can even pet some of the parrots and the entrance fee of ten dollars goes directly towards the garden’s upkeep.


  15. Chelsea

    Favorite is Irish Kevin’s. You guys have to try Hog Fish, in Stock Island. They have fabulous lobster bisque. Red Gardner Saloon is always good on the eye. Love the local spot, Hurricane Hole. And if you love great Cuban meal, check out El Siboney. Best Cuban sandwich is right by the laundromat Sandy’s (opened 24 hours.)

  16. Ciaran Smith

    Love the ideas! I have been to the Keys 6 times…my mom lives there all winter!! I love going to Aqua on Duval St. – super fun and really entertaining! Sunset cruise with Fury is really fun too! Great music and bottomless margaritas! Sloppy Joes Pizza is a must!!

    • Dang Travelers

      Oh Cairan, I think we need to become friends with your mom! 😉 how awesome. We will definitely hit these next time we are there. Key West is always a good idea!

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