Earlier this month, I extended a business trip in Florida to visit Key West for a long weekend. Key West has long been one of my go-to relaxation destinations. It’s well known that Hemingway loved Key West and lived there for a time, and visitors find lots of evidence of that fact including opportunities to visit Hemingway’s home and the places he frequented. I had a “Hemingway weekend,” filled with fishing, cigars and rum, as well as lots of live music, people-watching, and eating seafood at waterfront spots.
During this visit, I stayed at the historic Cypress House Hotel which dates back to the late 1800s. The location was perfect for my purposes. It’s just a few short blocks away from Duval Street, which meant I could go out for the evening on foot easily and get back home with no trouble. Additionally, the harbor area from which I would go fishing was just a few blocks walk in the opposite direction.
Among the things that I love about Key West are the sunset views from Mallory Square with sailing ships going by and the loud and colorful “cat guy” getting his trained cats to jump through fire rings. You can also see the big cruise ships come in and out of port. Key West has plenty of chances to eat a meal at an outdoor café with roosters and hens walking around freely, and there are galleries and live music venues everywhere. As a bonus, the place is filled with old seafaring hippies like me.
My plan was to go fishing on Friday and then out to the bars Friday night. Unfortunately, high winds kept the fishing boats at the docks, so I spent the day walking around town and visiting the Southernmost Point and other tourist spots, then had a late lunch at Conch Republic, and then visited lots of shops and galleries. That night I wandered around Duval Street, stopping at all my favorite live music spots like Sloppy Joe’s, Hogs Breath, Irish Kevins, Willie T’s, Margaritaville, Mangoes and others. The music was great, the people were friendly, and the drinks were good. I stayed out far too late given the planned early morning fishing start but somehow I dragged myself out of bed on Saturday morning in time to make it to the docks for fishing that day.
When I travel, I usually fish on charter boats. They are more expensive but the experience is usually a better one. This time, I chose to fish aboard a lower-cost head boat called the Tortuga IV for a half day from 9am to 1pm, fishing the reefs for yellowtail snapper, mutton snapper, grouper, and whatever else would bite. There were only 10 fishermen aboard, and the captain and mate were easy going and helpful. Things went well and It was a fun day, and while we hooked up often, the fish we brought over the rail were often too short to keep. Still, there were plenty of keepers for all to take home for a fresh fish meal, so we all went away smiling.
The mate cleaned our fish for tips and when I asked him where to take my fish filets to have them cooked for lunch, he pointed to Dante’s, a poolside bar and restaurant adjacent to the harbor. He said that Dante’s does a great job, so I took my fish a few short steps from the boat and sat down at a table with a view of both the harbor and the pool. When the waitress came over I ordered a rum drink and handed her my bag of fish filets asking for them to be cooked. She advised me on the options and I opted for ½ blackened and ½ fried. I was very happy with both!
After my late lunch, I cleaned up and changed clothes and then I walked down Duval Street for a visit to the Speakeasy Inn, a legit rum bar in Key West. I told the bartender what rums I like and asked her to teach me a new one. She did, pouring me a Ron Abuelo 12-year-old rum that reminded me of a few of my favorites. I’ll get that one again for sure.
I spent the rest of Saturday evening at the bars, meeting friendly people, hearing great live music, and even dancing some. As always, I came away thinking that Key West is a blast. Just ask the locals to tell you where they come from. More often than you might expect, their story is something like “I came down for vacation 8 years ago and never went home.” I have to say, that doesn’t sound entirely crazy.
Thanks for reading! A blog works best with active participation. If you enjoy this blog, please +1 it and leave a comment. Share it on your favorite social network. More readers will drive more discussion.