Islamorada’s Cheeca Lodge

The Florida Keys mainstay makes a luxurious base for an offshore adventure

April 4, 2012
Cheeca lodge travel
Cheeca is recognized as a crown jewel of fishing lodges. Courtesy Cheeca Lodge

Sometimes it seems like the icy hand of winter takes forever to release its grip. Ice storms, snow and freezing rain put a damper on most outdoor activities up north, and unless you’re one of those fellows who likes to get out on the ice, fishing is out of the question. Not so in sunny Florida! While it does get pretty chilly in northern Florida during the winter months, south Florida and the Florida Keys boast springlike temperatures and sunshine from October through June. Luckily for those of us who pursue billfish, the winter and spring seasons coincide with a tremendous sailfish bite down in the Keys, and there’s no better place to make your base camp than the luxurious Cheeca Lodge in Islamorada.

Located at mile marker 82 on the Overseas Highway, Cheeca Lodge sits on 27 acres of manicured paradise right on the Atlantic Ocean. Long recognized as a crown jewel of fishing lodges, Cheeca has hosted a veritable who’s who, including presidents, celebrities and fishing luminaries, in its 60-year history.

Mrs. Clara Mae Downey from Olney, Maryland, opened the Olney Inn in 1946, which later became Cheeca Lodge. Amazingly enough, Olney’s first guest was President Harry Truman, who cherished his time lounging around the pool and wandering amid the resort’s 22 quaint bungalows.


Even back then, the newly built Overseas Highway brought an influx of fishermen determined to take advantage of the exciting angling opportunities offered up by the Florida Keys. The lodge’s website says, “They came to escape the colder climates of the East and to enjoy a sportsman’s paradise. [The] Miami Herald newspaper reported, ‘Small wonder that so many sportsmen are attracted to the Keys. Here is the fishing ground of the world, where strikes are as frequent as sunny days, and specimens that would be record catches in other parts of the world are tossed disdainfully overboard to grow up.’” It’s no wonder that Islamorada came to be known as the sport-fishing capital of the world.

During the 1960s, the lodge came under the control of the Twitchell family. Cynthia Twitchell, also known as “Chee,” was an heiress to the A&P grocery chain. The name Cheeca actually came from combining Cynthia’s nickname with her husband’s first name, Carl. Under the Twitchells, the lodge underwent a major refurbishment, with the addition of the main lodge, more villas along the oceanfront, a golf course and Cheeca’s now iconic wooden fishing pier.

I got my first taste of the Cheeca high life about 10 years ago while fishing the Presidential Sailfish tournament that the lodge hosts every year. Our team fished out of Holiday Isle marina with Capt. Butch Green on Sassy Lady. Fishing was good, and the company was even better, and on the first day of fishing, I was sure I was going to win the thing. The 12-pound tourney starts right at 8 a.m. (at least it did back then) and by 9 a.m., I had already caught four and lost one. The bite was on! And then it turned off, at least for us. I don’t think we saw another fish after 9 a.m. that first day! However, that didn’t stop everyone else from stomping us into the ground during the rest of the tournament. I was fortunate enough to fish the tournament a couple of more times on Sassy Lady, and though I don’t remember a win, I sure remember the good times with Green and my wonderful stays at Cheeca Lodge. As of this writing, the 2012 Presidential tournament is just finishing up, and according to tournament director Liz Hill, the anglers enjoyed another successful event. “We had 27 boats and 95 anglers this year, and it seemed the teams were evenly split between Bud N’ Mary’s, Whale Harbor and Holiday Isle,” Hill says. That’s another great thing about Cheeca — it sits in close proximity to some of the most famous, and fun, fishing marinas found anywhere. For those not fishing the next day, there’s ample opportunity for revelry of all kinds.


I’d been trying to get back down to Cheeca Lodge for some time to do a Travel Briefs column. The main lodge underwent a complete renovation over the last several years after a fire damaged the roof and upper rooms of the main building on Dec. 31, 2008. The lodge wanted to get the word out that Cheeca was up and running and more beautiful than ever. An impending deadline prevented a trip down this past January to fish in the Presidential tournament, so I just figured I’d get down whenever I could.

Luckily, the first taping of the Chevy Florida Insider for 2011 was taking place on a Wednesday in the middle of my kids’ spring break down in Hialeah, Florida, on the outskirts of Miami. Since that’s almost to the Keys, I took a chance to see if Cheeca had any openings, so we could spend the weekend and I could get some info and photos for this story. I told them that we’d all (five of us) squeeze into a single room if necessary!

About two hours before I was to leave for Miami to tape the show, I got an e-mail from Cheeca’s Susan Ashmore that said that they had a room for us! The kids went berserk and scrambled away to start packing. My wife, used to my spur-of-the-moment adventures, blew the hair out of her eyes and headed after them, shouting orders on what to bring. After three rainy days in a row at home with the kids, my wife was already at her wits’ end, so I was cringing at the thought of a tense 3½-hour drive down the turnpike. Everything went incredibly smooth, however, and soon we were pulling onto the lodge’s immaculate grounds.


It took us about five minutes to check in, change and hit the pool — it had to be some kind of record. There’s nothing quite like sipping a frosty adult beverage at poolside, and Mother Nature blessed us with perfect sunny and breezy days. The kids spent untold hours trying to kill themselves (or each other) in the pool and were thankfully unsuccessful. We played golf on the lodge’s nine-hole course and biked all over the grounds — in short, the kids had a blast.

Although I’d brought enough gear to stock a small tackle shop, I didn’t get a lot of fishing in. I got up early one morning and slipped down to Bud N’ Mary’s to wander around and make a few casts, and was rewarded with a couple of small mangrove snapper on a Gotcha. They weren’t big, but they sure were fun to catch on the quiet, beautiful pink morning.

The kids were worn out on the ride home to Orlando, and so was I — the Keys and Cheeca Lodge had done their work perfectly.


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