Deep Sea Fishing Hemingway Style – Of Key West Legacies and Legends

The original Sloppy Joe's where Hemingway drank like a fish is now Captain Tony's.

Fishing is one of the most popular attractions in Key West and has been since legendary sportsman and acclaimed writer Ernest Hemingway put Key West on the Anglers’ Chart. It was 1929 when “Papa” discovered the big game marlin and sailfish that still draw visitors to the Southernmost City. He would fish and write in the Southernmost City for most of the next decade.

Hemingway didn’t fish for dinner – at least that isn’t the legacy that has been handed down; he fished for the trophies – marlin and sailfish twice his size, just as he hunted the big game in Africa. Size mattered, not dinner.

For visitors to Key West there are so many reasons to experience this legendary sport: many fish for dinner – there is nothing better than the fish you caught today; or for the delight of bonding with family and friends — or — like Papa Hemingway, they’re in for the thrill of the hunt!! The big game sport fish in the Florida Straits off Key West are gorgeous beasts of the sea that can provide an exhilarating chase that will satisfy even the most ardent of adrenaline junkies.

The fighting targets include shark, barracuda, mahi-mahi (dolphin), tuna, kingfish, yellowtail, marlin and sailfish. Shark and barracuda – with their fierce appearance and deserved reputation — and the agility and speed of the sailfish make them exciting catches in the sport of deep-sea fishing. Mahi-mahi’s iridescent colors and great size –  schoolies which are year round can reach 29 pounds – but 40 pounders are not uncommon in season — make them great prizes.

Depending upon the season, there will be a different type of fish that will bite. At the beginning of the year, in the height of winter, mackerel, sailfish and wahoo migrate off the coast the Florida Keys. In summer, there’s the chance to catch mahi-mahi, marlin and tuna. The vicious-looking barracuda are ready to give you the fight of your life all year round! Shark fishing is also year round.

If it’s the big game you want, a sport fishing charter yacht is the best way to go, but there are also less expensive choices: the “party boats,” which are 40 to 70 feet and can accommodate large groups of people. These are the most economical and, of course, the most social. On these boats, the crew will chum to attract fish under the boat so you and your friends can catch grouper, yellow tail snapper and mahi-mahi for dinner!

Backcountry/Light Tackle boats can hold a maximum of 4 people on its 21-35 foot length. These boats are for the adrenaline-seekers out there as the captains on this type boat use a spinning rod and reel combination with a lighter line. This lighter line means that fishing is more of a challenge! You are definitely in for a fight when you get a fish on the other side of that line! Light tackle fishing is especially unique to Key West as the captains there were the first to develop it, though it has become popular all over the world.

Flats boats are only able to hold 2 people as its shallow draft are only made for shallow fishing. These boats allow for sighting the fish and then sneaking up on them. Once you spot the fish, it’s up to you to catch them, so fishing on this kind of boat may take a little more practice, but the challenge is worth it. With this technique you are able to spot and catch shark and barracudas! Permit – the bulldogs of the back country, tarpon and bonefish are very popular targets with flats fishing guides.

When it came to fish, Hemingway went after the trophies.

When it came to fish, Hemingway went after the trophies.

Sport-fishing yachts are for the most dedicated sport anglers who are interested in all the various ways of catching these unusual fish. Holding up to 6 people, they are more expensive but have a more detailed offering, for example: trolling – baiting fishing lines and drawing them through the water, kite-fishing – using kites to hold bait on the surface of the water to attract fish like sailfish, night fishing trips, Marlin tournaments and even charter trips to the Bahamas and Cuba.

As deep-sea fishing is such an integral part to tourism in Key West, most hotels will be able to advise anyone who is new to fishing on the best kind of boat and captain in the area. Successful sport fishing requires an experienced captain and that may not coincide with the cheapest. However, investing in a reputable charter will help to provide adrenaline-charged fun and, perhaps, if it is edible, a very tasty fish. Lastly, for the best prevention of seasickness, it is best to take medicine a few hours before boarding, as once you are on the boat and begin to feel a little off, it is too late!

When you are safely back on land, you’ll want to be sure to indulge in Papa’s other legacy to Key West – the nightlife, and in particular the famous Hemingway haunt, Sloppy Joe’s. On the corner of Greene Street and Duval, you’ll find a non stop party any time of the day. This is not the original Sloppy Joe’s, though – Papa’s original bar stool was a few doors down Greene Street in a dark hole of a tavern now called Captain Tony’s. Raise a glass and throw one back for Papa as you come to know: from the waters of the deep blue-green to the watering holes on a Duval Crawl, Key West lives up the legends and legacies of the “Old Man” and the Sea.

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