Over the years, I have traveled to the Florida Keys many times, starting when I was a teenager. Back then I, my Dad and brother would drive down to Miami to meet my uncle and three cousins. From there, we drove another 4 hours south on two-laned US 1 towards Mile Marker 0 for lobster season. After checking into our hotel rooms, the seven of us then piled into a rented 20 foot open fisherman with our snorkel gear, and coolers filled with ice and food. We headed offshore in search of the best “honey-holes”, where savory Florida lobsters were just waiting to be plucked from the sea.
Back then, Key West was not the bustling tourist town it is now. Hotels and restaurants were small, family owned operations, unlike the 4 and 5 star resorts that cater to pasty-white tourists these days. Nor were there any mega-cruise ships, which once docked, disgorged 3000+ passengers like a plague of locusts on the town.
Key West’s history begins with its European discovery in 1513 by Ponce de Leon. The island was named Cayo Hueso, Spanish for Isle of Bones. Apparently it was covered with remains from an Indian burial ground or battlefield. Much later, some marketing genius renamed it “Key West”, a friendlier, English version of the Spanish term.
Since getting my pilots license, flying private to Key West has been a regular occurrence. What used to be a nine hour drive from Central Florida is now just an hour and a half flight in the Bonanza.
Our usual routing is direct to the Lakeland VOR, Victor 7 to the Lee County VOR, then Victor 225 to STING intersection. From there, Navy-Key West Approach takes over and issues vectors to arriving aircraft for Key West International Airport (KEYW).
On most flights we file IFR for nine thousand feet. This gives us a great view of the Everglades to our left, and plenty of gliding range in case of an engine-out. Fortunately, the 95 mile open stretch of water between Naples and Key West is warm, clear and fairly shallow. Boats are plentiful in the event you need to ditch. Be sure to pack an inflatable raft and a USCG life vest for all passengers on board, along with a survival kit including a hand held radio, some water, a signal mirror and first aid items.
About halfway across the water, you may hear “RADAR contact lost” from Miami Center, indicating you are out of RADAR range. Don’t worry. As you get closer to the islands, ATC will pick up your transponder again.
If you are less adventurous, or don’t particularly like flying over open expanses of water, head direct towards Key Marathon, (MTH) in the middle Keys. Then descend to 1,000 feet MSL and turn southwest along the island chain towards Key West. Stay clear of Navy-Key West Airspace, or get RADAR service from them if VFR. The Navy does not really care for civilian aircraft popping into their airspace unannounced.
Be sure to familiarize yourself with Restricted Area-2916, northeast of Key West. This area contains a large tethered balloon, affectionately known as Fat Albert, on a steel cable to 14,000 feet MSL. This surveillance balloon allows Customs to watch for low flying aircraft smuggling drugs into the US. A few years back, a Cessna 182 inadvertently flew into R-2916 at night and had an unfortunate encounter with the airborne cable, slicing the wing off.
Once you reach the Key West Airport Traffic Area, ask the Tower for the “Island Tour”. If the pattern is not too busy with Beech 1900 or ATR commuter turbo props filled with sunburned tourists, you can fly clockwise around the scenic island at 1000 feet. When you are ready to land, request right-traffic for RWY 9, and turn final over downtown and Duval Street.
After touching down, taxi to Island City Flying Service, Key West’s only private FBO, just west of the commercial terminal. From there, Old Town Key West and Duval Street are just a 10 minute cab ride away.
Dining wise, Key West has many choices. Bagatelle and Antonia’s Restaurant are both right on Duval Street and are great for watching people doing the “Duval Crawl”. Louie’s Backyard is also a family favorite.
For sunset celebrations, first-time tourists typically go to Mallory Square, on the docks. Starting an hour before sunset, you will find a crowded, carnival-like atmosphere with lots of street performers and vendors. Once you have done that a few times, take my advice and head over to the historic Crowne Plaza La Concha hotel on Duval Street. Then, take the elevator to the top of the building. At 7 floors, the La Concha Hotel, built in 1926, is the tallest building on the island. The quiet, outdoor roof-top bar is above the bustle of Duval Street and is the perfect spot to view a beautiful Key West sunset.
The La Concha is also the starting point for a Ghost Tour (You’re Doomed!) of old town Key West. Also check out the old City Cemetery. The cemetery is located on the highest point of land on the island, 7 feet above sea level. All of the graves are in above ground crypts, many dating back hundreds of years. Creepy. If you go, be sure to look for the Vampire Crypt!
No trip to The Conch Republic is complete without a tour of the Hemingway House and a stop at Sloppy Joe’s Bar on Duval. Most people don’t know the original Sloppy Joe’s, where Hemingway hung out, is actually around the corner on Greene Street. It was located at a bar now known as Captain Tony’s Saloon. It’s a real dive.
Some pilots are uneasy about flying their own aircraft to Key West, especially over the Gulf of Mexico. Actually it is a very easy trip, and it does not involve getting an eAPIS approval from DHS/Customs required for flying to the Bahamas. Flying down Victor 225 will keep you clear of the ADIZ.
There are a couple of things I would avoid. The first is Key West during the sultry months of July and August. The heat and humidity can be oppressive, despite an occasional sea breeze or shower. Secondly is Jimmy Buffet’s Margaritaville. Unless you like hanging out with a bunch of drunken Parrot Heads, decked out in Tommy Bahama shirts, singing “fins to the left, fins to the right”.
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