See You at Sunset : Mallory Square ~ Key West

“Another day in this carnival of souls. Another night settles in as quickly as it goes. ”  Unknown

To celebrate the close of another day in Paradise, visitors find their way to Mallory Square located on the waterfront in Key West’s historic Old Town, overlooking the tranquil Gulf of Mexico. It is here where jugglers, psychics, musicians, artists, and food vendors gather to entertain and feed the tourists and have some fun. Get here early to feel the carnival like atmosphere and then stand back, ooh and aah as the sun sets.

Dominique and his Flying House Cats put on an entertaining show while  coaxing them through hoops of fire. There have been several “cat men” over the years, but Dominique seems to get the most attention.

Mallory Square, Key West, FL       Mallory Square, Key West, Flo

Part of the sunset ritual is jockeying for position to get the best views while watching the catamarans sail by.

Mallory Square has a long history as being a center of activity in Key West. Once it was the chosen anchorage of pirates, and has also been the center of the wrecking industry and the assembling point of American forces for four wars.

Many noted figures have enjoyed the view of sunset from Mallory Square over the years. Audubon wrote glowingly of the glorious Key West sunsets while visiting in the early 1800’s, and legend has it that Tennessee Williams initiated the ritual of applauding the sunset at Mallory Square, gin and tonic firmly in hand.

As you can see, the island is a mix of creative and eccentric characters with carefree attitudes. It is just the way the natives like it; definitely a laid back kind of life.

Mallory Square, Key West, Flo

About travelerlynne

Traveler. Writer. Retired Educator.Traveling on and off the beaten path with my photographer husband. Volunteering locally as well as in Haiti and Tanzania, an enriching and humbling experience. A sun lover! Shelling, boating, fishing and watching sunsets. Growing mango, banana, key lime,and pineapple.Making smoothies and chutneys. Enjoying family and friends! Savoring each new day!
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26 Responses to See You at Sunset : Mallory Square ~ Key West

  1. I was at Mallory Square watching the sunset many moons ago, during my honeymoon for my first marriage. We spent our honeymoon in Islamorada and spent a day or two in Key West. That was in 1979! So so long ago! Beautiful photos. 🙂

  2. What a great place to spend an evening, Lynne. I’d love to see the flying cats. I didn’t know that cats could be trained to do tricks. 🙂 Mallory has a very interesting history, and I would love to go there to experience the festive atmosphere and that spectacular sunset.

  3. i spent a new year’s eve there – wow, what a bizarre evening!

    i’m home and shocked that the usb modem loaded this page! yeah!


  4. Ingrid says:

    I have yet to make it to Key West but it’s on my list…..looks too fun to miss 🙂

  5. Mallory Square! So much fun and so much to see there! Do they still sell the delicious banana bread?

  6. I didn’t notice any, but that doesn’t mean it wasn’t there. Lot’s of people, even though it is off season.

  7. restlessjo says:

    That header is glorious, Lynne. I’d love to go catamaran gazing right now 🙂

  8. I’m a sucker for anything around the water and sailing is one of them. 🙂

  9. Gigi Galore says:

    I keep trying to comment on this and it never wants to show up! This is kind of a mic test ..”one, two three…”

  10. Gigi Galore says:

    Okay, that worked 🙂 Here is my original comment, which I saved just in case … 🙂 :Yes, we’re going there one day for sure now! Applauding the sunset? What a sense of occasion! I’m all for applause and celebrating occasions. Hard to word it … but anyway, just clap! 🙂

    Hope it was worth it, the
    comment, that is 🙂

  11. I applaud your determination to celebrate our Key West sunsets, Gigi. :). And your comment was, of course, so Gigi like, fun, and worth it. 🙂

  12. Apologies for taking a while to get over here – I’ve been finding myself busier than I would like of late. But what a strange and wonderful place. It reminds me a little of a Hilltop Bar I went to in Bali – minus the Flying House Cats.

  13. I missed Hilltop Bar in Bali. Mallory Square can be bizarre most nights which must be its appeal. 🙂

  14. Madhu says:

    Applauding the sunset and those incredible cat performers Lynne!! I had no idea that ritual (of applause) was initiated here! Have always felt self conscious doing it whether in Santorini or Siem Reap 🙂

    • It is so laid back in Key West and can be a party town, especially at sunset. Applauding is spontaneous and a given. I’ve also been in places w here I was self conscious, but if someone starts it, I will join in. 🙂

  15. Sunset at Mallory Square – the perfect place to be.

  16. One of those Key West traditions that I’m glad still goes on. 🙂

  17. vbholmes says:

    Gorgeous photos, Lynne. A while ago (actually quite a long while ago), I was there in October when Key West was chock full of divers–it was party time all the time. Fun.

  18. Yes, it is party city. In fact, they are proud of the pub crawl theme. Some times we just have to have a little fun. Thanks for commenting, VB. Are you traveling this summer?

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