“The days drift by, they don’t have names, all of the streets here look the same…there’s so many quiet places, smiling eyes match the smiling faces…I have found me a home”
– Jimmy Buffett [lyrics from “I have found me a home” in reference to his first couple months living on the island of Key West]
I have received numerous inquiries in the past few weeks about the Florida Keys and Key West; namely, because several friends and family members will be retreating to the United States’ southernmost island in February, March and April, and asked me for numerous recommendations, which ultimately warranted this blog post.
My obsession with Jimmy Buffett and Florida started when I was a kid, road-tripping to Florida and stopping in Jekyll Island, St. Augustine, Siesta Key, and eventually Englewood. However, I had never been to “Buffett Land,” also known as Key West. He was the first road-tripper from Nashville all the way to Key West, taking notes on his observations, and of course, which places had the best grouper sandwich and ice-cold beer. Countless hours of research, phone calls, and e-mails have resulted in the creation of a “Buffett-inspired itinerary,” so you can follow in the footsteps of his first adventure through the Florida Keys and eventually, Key West in the early 1970s.
You can find out more about the trip in Jimmy Buffett’s memoir, A Pirate Looks at Fifty, in which he describes the trip through the Keys as very “Kerouac-like” (author of the 1957 counter-cultural novel On The Road), and talking about what he felt at that time, which ended up being the trip that quite literally changed his life. Two other great books that contain information about the early years and Key West are A Good Life All the Way and Jimmy Buffett: The Key West Years. One final recommendation: buy the Essential Book of Boat Drinks – you’ll thank me later.
Pre-Trip Planning
- Book one-way ticket to Miami, FL from your home destination, with an early morning flight departure (6am)
- Contact one of the car rental companies (Hertz, Turo app, etc.) in the Miami airport and rent a convertible, or similar vehicle in which you can take the top down (we rented a black Mustang Convertible) so you can truly feel and enjoy the experience (Seven Mile Bridge, etc.)
- Book one-way ticket back to your home destination from Key West (for the day you plan to leave). Or, if you have the time, drive back up to Miami from Key West and stop at some of the places you may have missed
- If you happen to be staying one night in Miami – please, go to Mac’s Club Deuce. The place is something out of a movie (actually a lot of the neon memorabilia is leftover from the filming of Miami Vice). It was Anthony Bourdain’s favorite bar in Miami, and you should go so you can find out why. If anything, it is simply a quiet refuge away from the madness and the oppressive heat of the Miami strip. It is, I gathered, the oldest bar in Miami.
Florida Keys Itinerary
Once you leave Miami, it is about a 45-minute drive on US 1 until you reach a fork in the road – it is imperative at this point that you take Card Sound Road, which is the more scenic route and reminiscent of “old Florida,” and will also lead you to the first stop on the Itinerary, Alabama Jack’s.
Stop 1: Alabama Jack’s, Key Largo
Alabama Jack’s is an old crab shack reminiscent of “old Florida” that consists of plywood and a tin roof. But don’t be fooled – over 50 years old, this is a favorite dining and watering hole for locals, Buffett acolytes, and road-trippers alike. The bar overlooks a channel and sits between the mangroves, and often pelicans and alligators may pay you a visit. According to Buffett, get the grouper sandwich, some conch fritters, boiled shrimp, a few crab cakes, and in true Jimmy fashion: ice cold draft beer.
“There were several locals peeling shrimp at a wooden picnic table, tossing the hulls into the ocean…commercial crab boats lined the wharf…and a squadron of brown pelicans law in wait atop the dock pilings at the sight of shrimp hulls hitting the water” – Buffett on Alabama Jack’s, early 1970s
Stop 2: Caribbean Club, Key Largo
Second stop on the Buffett inspired road trip is the Caribbean Club in Key Largo. This is the actual site of the famous Humphrey Bogart and Lauren Baccall movie classic, Key Largo directed by John Huston. The back deck adorned with palm trees and a few docks, is still is basically untouched from the famous scene in which Bogie thwarts the gangsters plan to escape. The bar is a classic old Florida bar and vibe – old film memorabilia, pool tables, jukebox, interesting signs and wood carvings, and locals drinking Coronas accompanied by a pack of Marlboros and stories of the day’s fishing conquests. To this day, it remains one of my favorite beach-style bars because of the rarity and uniqueness as these bars do not really exist anymore.
“It was a bar like many others, but it wasn’t….faded stills from the classic movie lined the walls…I tried to place the real location with the action from the movie, and then walked out to the pier where Bogie thwarts the escape of the gangsters…I sat there and sipped my beer…knowing I would be associated with this world [Florida Keys and Key West] for the rest of my life…” – Buffett on the Caribbean Club, early 1970s
Stop 3: Robbies Marina Of Islamorada
Robbie’s Marina is a must-stop – voted one of the best stops in keys – grab a fresh grouper sandwich at the Hungry Tarpon Restaurant, a Rum Swizzle with Pilar Rum at the Thirsty Tarpon Bar, and check out the Tropical Open Air Market. Also, make sure you feed the tarpon, it is a great experience.
Optional Keys Bars (If You Don’t Want Your Adventure to End)
Lorelei Restaurant and Cabana Bar, Islamorada, Sunset Grille, Marathon, FL; No Name Pub, Big Pine Key, FL
Key West Itinerary
Lodging
I recommend you stay at the Casa Marina Resort (where we stayed) or the Southernmost Beach Hotel, or somewhere in that general area of the island. It was nice to party on famous Duval Street, and then have the option to retreat back to the quiet grounds of the resort and have a drink on the private, secluded beach. This area of the island is also convenient, because you are right next to the Southernmost Point Buoy which is an awesome place to take a picture as it is the literal Southernmost Point of the Continental Contigious United States – get there early, because it becomes insane with a tourist line by 9am. Lastly, you are also a two minute walk to one of the island’s best restaurants and bars (and my personal favorite), Louie’s Backyard.
First Order of Business (After Check-In)
Rent bikes! Make sure you rent bikes – I can not stress this enough. The island gets congested very quickly and early, and it is so easy to navigate and see so much more with your ten-speed. And yes, there are coozies attached to the bikes for those that want to do the “Duval Crawl.” Once you have a bike, the world is your oyster.
Bars, Pubs and Saloons
There are bars up and down Duval Street, but many of the famous ones are clustered towards the end of Duval, near Mallory Square. From the hotel, it is about a 15 minute walk; on bikes, 7 minutes.
*Favorite Bar/Restaurant Combo in Key West* – Louie’s Backyard
Because of the ambiance, view, historical aspect, as well as excellent food and drinks. Louie’s Backyard, by far, is my favorite bar in Key West. It is the restaurant in which Buffett started playing in the early 1970s in exchange for beer instead of money; where he was married and divorced (not on the same night); and where he eventually landed an apartment next door and wrote the song “Tryna’ Reason with the Hurricane Season” about a hangover and not being able to “go at this pace very long” in which he stumbles over to Louie’s to get a much needed Bloody Mary.
Enjoy your time at Louie’s and savor the experience – also make sure you buy the Louie’s Backyard Cookbook, it is awesome!
*Second Favorite Bar* – The Chart Room
Because of vibe, uniqueness, and historical aspect, The Chart Room (Inside the Pier House Hotel) is my second favorite bar in Key West. After Louie’s you should immediately go here before it gets too crowded. This is a bar that has solidified itself against time, and was traversed by Jimmy Buffett, Hunter S, Thompson, Jim Harrison, Tom MCGuane, and may other famous literary giants, artists, and musicians. This is one of the old bars left of “Old Key West” and one of the former bartenders, Phil Clarke, was Buffett’s friend and inspiration for the famous song “A Pirate Looks at 40.”
*Third Favorite* – Schooner Wharf Bar
I love Schooner’s because it is an authentic Key West fisherman’s bar. Tall tales, awesome live music, happy and hour is from 7am to 11am. I inquired why so early, and the waitress responded: “how can you drink all day if you don’t start in the morning?” Also, while you are at Schooner’s make sure to visit Shrimpboat Sound, Jimmy Buffett’s recording studio!
*Fourth Favorite* Captain Tony’s (Authentic Key West Bar, original Sloppy Joe’s)
Captain Tony was the Mayor of Key West thanks to help from Buffett. The song “Last Mango in Paris” is about Captain Tony, and all he did for Jimmy in his early years in Key West. By the way, Captain Tony’s is the original Sloppy Joe’s Bar, where Ernest Hemingway would often frequent. Toss a quarter into the grouper’s mouth while you have your back to it after a couple drinks – allegedly it is good luck (or the bar just gives you a free drink. Either way, enjoy!
Other Favorite Bars (With Great Live Bands, Great Drinks, and Good Vibes)
Sloppy Joe’s (not the original), Irish Kevin’s, The Coconut Man in Mallory Square, Hogs Breath Saloon, Willie Ts, Original Margaritaville (get a margarita, they are incredible!), and Green Parrot Bar
Restaurants
*Personal Favorite* – Louie’s Backyard – incredible restaurant right on the ocean. Great spot for pre-gaming before heading out to Duval, or getting dinner on the way home after an early Duval trek. Also the restaurant deck is where Jimmy Buffett started out playing gigs in the 70s for free beer as his apartment was next door.
Breakfast
My favorite breakfast spot in Key West – cats run wild, chickens roam the grounds, and people start drinking champagne at 7am. Make sure to get the lobster benedict, and try the whipped Key Lime Pie!
Pepe’s Cafe, Banana Cafe, Le Crepere Cafe Key West, Cuban Coffee Queen
Lunch
B.O.s Fish Wagon, DJs Clam Shack, Thirsty Mermaid, and Moondog Cafe
Dinner
Get Dinner at Latitude’s on Sunset Key
Sunset Key is only a 5-minute ferry ride from Mallory Square in Key West. Latitudes, is the bar and restaurant on the island, and it makes for a wonderful evening for dinner. If you can, definitely go.
Louie’s Backyard – can’t stress it enough! The place is the real deal.
Other dinner spots: Santiago’s Bodega, Thirsty Mermaid, Blue Heaven, and any of the bars mentioned above
Dessert
My favorite dessert of all time is Key Lime Pie, and the limes, are from Key West and the surrounding island. They are different than other limes. I think I tried the Key Lime Pie at eight restaurants. They were all incredible – Kermit’s is up there. Enjoy!
Activities
Papa’s Pilar Rum Distillery (Hemingway’s Family Distillery), Key West First Legal Rum Distillery, and Key West Trading Company
One of my favorite activities in Key West, was the tour of Hemingway’s House, which we did twice. He remains one of my favorite authors, and deserves so much respect for his contribution to the literary world in America. He lived in Key West from 1931-1939, and did some of his best writing in the studio that is connected by a bridge from his main home. He was so disciplined, that he would get up at 6am, no matter how hungover, and write until about 11am. He then would then trek to Duval Street and drink at the Original Sloppy Joe’s (now Captain Tony’s) and eventually stumble back to his home at night (using the Key West Lighthouse as his compass). And then do it all over the next morning. A true American legend and icon.
Shrimpboat Sound
This remains Buffett’s music studio, aptly named “Shrimpboat Sound,” which is still in use today and was used to make his most recent album, Life on the Flip Side. You will be able to recognize it by all of the stickers; it almost looks like a big white shipping container. When we were in Key West, we just missed Kenny Chesney leaving the studio; presumably recording a new country song with Buffett.
Other Activities
Get dinner on Sunset Key, catch a Mallory Square sunset, Butterfly Museum, bike to Fort Zachary Park and have lunch, Key West Conch Tour, Key West Lighthouse Tour, Harry S Truman White House Tour, ferry to and snorkel Dry Tortugas National Park, scuba diving around Key West, rent jet skis, rent a boat to the Snipes Keys or Ballast Key, go fishing for Tarpon, venture to Stock Island and check out Higfish Bar and Grille and have your fish you caught filet in front of you and cooked, check out the Key West Bookstore, picture at the “Mile 0” marker
Most importantly, the Keys and Key West are about going with the flow and doing what you feel is fun at the moment. Go down some side streets. Pop into a corner a bar not listed on this guide. Bike to an off-the-beaten-path beach. The island has a great vibe and you will love it. And, most importantly have a lot of fun and make some wonderful memories.
If you are not going to Key West this winter, here are a few books and early Buffett albums that are directly related to the Keys and Key West that can take you there.
Suggested Reading: A Pirate Looks at Fifty, Jimmy Buffett: The Key West Years,
For True Parrotheads: A Good Life All the Way, Captain Tony: Life Lessons from a Legend
Early Albums on Key West: A White Sport Coat and a Pink Crustacean, Living and Dying in 3/4 Time, A1A, Havana Daydreamin’, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor
*If you use this guide, please drink responsibly
