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29 Favorites about Key West.

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For the “Leaplings” celebrating their actual birthday this year, here are our 29 favs about Key West. These are in no particular order, except the 1st one.

  1. The People. The motto in KW is “One Human Family”. Ever so true. The warmth and true sense of community is very real and incredibly unique.
  2. Kayaking. Actually, kayaking Cow Channel then cutting down through the riviera, finding the slivers through the mangroves to get to the salt pond. Absolute tranquility.
  3. Bootle. For a throw-back night, drop by Mangoes on a Thurs/Fri/Sat and Dave Bootle’s combo DJ/Singer performance will have you swinging to EWF “September” or any of that genre classics.
  4. Anna Sweet. Key West artist & gallery owner. Incredible talent. Wine connoisseur, vintner and just a down-home all-around good person.
  5. Sunset Pier. “Practically perfect in every way.” Mary Poppins may/may not be there when you swing by…but you will find: Perfect outdoor venue to enjoy the live music, great food, great people about, cold beer, good pours, quick service, and views that will knock your socks off. Go west on Duval until your next step is water…there you go. Best Tiki Bar in South Florida.

  6. The corner of the beach at Fort Zach closest to the jetty. Much more sand, much less coral. Wide open vista. Nice palm tree on the beach edge to set-up under. Although, now that I think about it…dibs. It’s a horrible place to set up. Go away.

  7. Sound Check. Catch up with your friends at least 1x/week by showing up at 5:30pm for the 1st set of the weekend band. Mostly locals, or near-locals, or been-here-so-often you look like locals. Oh….where? Read a little further.
  8. Bingo at the Parrot. I took a visiting friend into the Green Parrot on a Monday evening. About 100 people there. Dead silence, everyone staring downward. Then you here, “B-5”. All playing bingo, all for charity. Lot of fun. Yep, same place as Sound Check.
  9. Popsicle Cart At Higgs BeachHomemade popsicles. Cream and water-based. Fun flavors. Sooo good. Her name is Kim. Transplanted to KW, and one of the reasons #1 on this list is #1.

  10. Mid-day, Key Lime Pie at the Blue Heaven Bar, with a fresh Hendrix. If you’re going to the shrine of Key Lime Pie, that’s how to do it. Live music is always low-key, little blue grassy, and local artists. Ping-Pong winner gets a pass on the bill.
  11. Bike ride the CemeteryStop at the welcome station (hmmm…that sounds like Beetlejuice) and get a map. Then find our favorite epitaph, Ms. BP Roberts, “I told you I was sick.”

  12. Grotto at St. Mary'sFind a little solitude and peace in your active life. Tuck yourself away in one of the most tranquil, peaceful spots in Key West. Just get lost in your thoughts, work through something challenging you, or just reflect and be thankful.
  13. Nobody Cares. No pretenses or BS. Whatever your status…it’s just about the fabric of who you are, not what you are, that carries the day. You could be anywhere on this island, on one side of you a boat washer, the other side a yacht owner. All the same.
  14. Alex Hennesy’s Hand Crafted Mojito. Drop dead serious…absolute classic, each build to perfection, which includes raw turbinado sugar---nothing “pre-mixed”. 
  15. In the day. Sunset from the top of La Concha. Not accessible anymore, but wow…maybe we start a petition/uprising to bring just a part of that back.
  16. Sunsets. Truthfully, from anywhere you can snag it. From Ft. Zachto being on a boat, to Mallory Square to Sunset Pier…just allow yourself to pause a few minutes and say thanks for another great day in paradise. Then onto the evening!
  17. Crystal Clear Waters. Get on a boat, kayak, paddleboard, walk the waterfront, whatever…just take in the gorgeous crystal blue waters that surround this island.
  18. Marquesas Fishing. Key West has one of the most diverse fisheries in the world. We like the solitude of running out to the Marquesas Islands, exploring a bit, and testing ourselves against those elusive permit fish. Actually, you can have great fun fishing right in the harbor. It doesn’t need to be a big event, but get the line wet and have a little fun.
  19. Beach at Boca Grande. OK, this one requires a little work and a boat. But a truly relaxing day is packing a picnic, some good friends and anchoring next to the beach on this preserve. Some areas off-limits, but you’ll appreciate the rawness of this deserted key.
  20. Whatever band is at Virgilio’s. There’s a little bit of a “speak-easy” feel, blended with a truly unique venue for some true, soulful, original, bluegrass. Grab a classic martini, sit back and ask yourself…”who are these guys”. Some nights, looks like they teleported from the back hills of Tennessee.
  21. Slipping into St. Paul's. Duval street can be a bit of carnival at times. Escape it for a few minutes, appreciate the beauty of this church in the middle of the chaos, give yourself a break, think, reset, reflect and appreciate this oasis.
  22. The lights during the Holidays. It really doesn’t take much to get this town to celebrate, but whew…they transform it to just a warm weather, winter wonderland. If you weren’t in flip-flops, you’d swear you were up north.
  23. Late night Bolognese, glass of red wine, at the La Trat Bar. Sometimes you just need quality comfort food, a welcoming smile, decent glass of wine and light conversation in an intimate setting. Grab a stool and watch the goings-on from inside the window.
  24. People watching from the benches at Court House DeliFind you way over to Whitehead, grab a sandwich & Dr. Pepper (or whatever your fav is), and just watch the traffic. Although, just about any place in town works for people watching, this one has an interesting cross-flow of people.
  25. Walking the docks around Key West Bight. From the ferry terminal, it’s about a ½ mile meandering stroll. Early morning as the town rises, but anytime is worth it. Genuinely….take your time, wander, take in the shops, grab a cold one, coffee and watch the world go-by, but just one of heartbeats of the town.
  26. Cuban Coffee. Truthfully, there are a number of great places from the back of The Five Brothers to the Cuban Coffee Queen. It’s rare to not get a well-made Cuban Coffee anywhere in this town. Your biggest decision will be sugar/no-sugar.
  27. Late Karaoke at Bobby’s Monkey Bar. Highlight your talents to the scouts from the Nashville record labels right here. As midnight passes, the talent (and courage) just gets better and better. Great equipment, broad selections, and an audience waiting for you. Swing by…but bring a great big smile, cheers for whoever is “on-stage”, and warm-up those vocua=cal cords!
  28. Conch Republic IndependenceWell, this about captures the mindset. It’s more of a “micro-nation”. The secession was on April 23rd, 1982. And now…one hell of an annual Independence celebration. I don’t’ think there is another town in the “lower 48” that takes “celebration” more seriously. It’s a full week of activity, to include the battle reenactment with the US Coast Guard.

  29. The Mermaids.

    The magic of mermaids, their benevolence and influence are evidenced through-out the town. But ya know, sometimes you just have to take that “leap” of faith and believe.


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