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Places (POIs) visited during this tour

Place #1
Distance: 1.28mi , Attraction : Former bar and music venue
Map Pin
5300 Overseas Hwy, Naval Air Station Key West, FL 33040, USA
POI 1 Tour Image
The Lantern Inn/Chico's Cantina
Though it’s now the home of Chico’s Cantina, the Lantern Inn was a regular stomping ground for Jimmy while he wrote his second and third Key West albums. Living and Dying in ¾ Time and A1A both came out in 1974, and even though they weren’t big commercial hits they’re still fan-favorites. The song “Nautical Wheelers”, which contains the title lyric of Living and Dying in ¾ Time but appears on A1A was filmed here at the Lantern in the late ’70s. Check out the video on YouTube when you get a chance – It’s a brilliant window to the past and features some very amusing dancing.

The Lantern Inn is one of the places that helped Jimmy find his signature sound, which he once referred to as “drunken Caribbean rock n’ roll.” Even though he has since started calling his genre “Gulf and Western,” His lyrics often mention an adult beverage or two, served up ice cold at spots like the Lantern Inn. It’s rumored that a conversation with a stranger here became the basis for his song “Son of a Son of a Sailor”

Today, Chico’s Cantina serves Tex-Mex favorites, like enchiladas, burritos, and tostadas – and of course, they make a mean margarita.

Place #2
Distance: 2.76mi , Attraction : Former Home of Jimmy Buffett
Map Pin
1511 19th St, Key West, FL 33040, USA
POI 2 Tour Image
3750 Sunrise Lane
If you look down the private road to your left, you may catch a glimpse of Jimmy’s last house on the Key. Owned by Buffett until 1998, the estate sits at the end of a peninsula and is surrounded by water on three sides. The road leading to the house itself is private, but if you happen to take a boat or jetski through the Riviera Canal you may be able to see the building from the water.

The 5,300 square-foot home has five bedrooms and four and a half bathrooms; it sold for 1.5 million dollars back in ‘98. Reportedly, various references to Buffett’s music are scattered throughout the grounds, including a marble shark fin statue in the garden denoting his fan-favorite tune “Fins”.

This beautiful estate may have been where Jimmy has ended up, but his time on Key West started from humble beginnings. As you head toward Jimmy’s apartment on Waddell Avenue, I’ll tell you a little bit about Jimmy’s early days on the island.

Jimmy came to Key West for the first time with his friend Jerry Jeff Walker and Jerry’s wife, Teresa Clark, in 1971. After a failed marriage in Nashville and two unsuccessful studio albums, Jimmy needed a “change in latitude”. He stayed with Jerry Jeff at their Miami home for a while and accompanied them on vacation to the Keys. He packed everything he owned into Jerry Jeff’s silver 1947 Packard and headed down route 1.

Jimmy’s early years were spent busking in Mallory Square, and performing at several spots that we’ll see later on. To make ends meet in the early days, Jimmy had a job as a mate on a fishing boat called the Petticoat III. Jimmy had a superpower to make friends with everyone he met, and the Petticoat’s Captain Norman Wood was no exception. Even as Jimmy got more well-known, the job was always made available to him when he needed some extra cash or a helping of fresh-caught fish. When his album A White Sportcoat and a Pink Crustacean was first pressed, it had its island debut in Norman’s living room.

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Place #3
Distance: 0.29mi , Attraction : Former Home of Jimmy Buffett, Restaurant
Map Pin
717 Waddell Ave, Key West, FL 33040, USA
POI 3 Tour Image
704 Waddell Ave and Louie's Backyard
During the mid-to-late ‘70s, Jimmy rented an apartment here at 704 Waddell Avenue. The white building with the balcony railing on the left-hand side is now part of the Coconut Beach Resort.

The apartments have been updated quite a bit since Buffett’s days as a young songwriter, and are offered for sale as condominiums or timeshares. The building’s many porches and balconies overlook a pool area and private stretch of beach. It’s possible that the famous “front porch swing” mentioned in “Margaritaville” was at this very location.

Two doors down from Buffett’s apartment, you’ll pass Louie’s Backyard, a famed Key West dining spot mentioned in Jimmy’s song “Trying to Reason with Hurricane Season”. Back when Jimmy lived on Waddell Avenue, Louie’s was a very different spot.

Louie Signorelli turned his historic Victorian home into a small bar and restaurant in 1971. For over a decade, the spot only seated 12 and was managed by a single waiter. It was here that Jimmy would sing for his supper, racking up a meal tab that often went unpaid. In 1983 the restaurant was purchased and renovated into the establishment you see today.

Today, Louie’s has three distinct dining areas. The main restaurant offers a fine dining experience, with internationally-inspired food by veteran chef Doug Shook. The menu changes seasonally, so there’s always something new to experience. The Cafe at Louie’s offers panoramic ocean views and pairs fine wines and small plates for European-style dining. Menu highlights include fried artichokes and grilled octopus.

Louie’s Afterdeck Bar, located behind the house, offers their most casual experience. The deck juts out over the ocean, offering gorgeous views on three sides. The Afterdeck serves craft cocktails and fine wines, and you can even bring your dog! Louie’s serves a weekend brunch menu, complete with a separate cocktail menu; just like Jimmy said in the song, you can still stumble over to Louie’s Backyard for a Bloody Mary. After passing Louie’s, hang a right on Vernon and a left on South Street to reach our next stop.

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Place #4
Distance: 0.71mi , Attraction : Landmark
Map Pin
507 South St, Key West, FL 33040, USA
POI 4 Tour Image
Southernmost Point and Historic Duval Street
Straight ahead, you’ll find the concrete buoy that marks Key West as the southernmost point in the continental United States. While this landmark is an iconic part of the Key West experience, it’s not exactly true. The southernmost point can be found on Ballast Key, one of several islands west of here that fall south of this point. Heck, this isn’t even the southernmost point of Key West! That’s located at Whitehead Spit on the grounds of the naval base just west of this spot.

Instead of passing the buoy, take a right and head up historic Duval Street. This is the island’s main drag, and is home to bars, shops, restaurants, and a whole host of tourist traps.

Place #5
Distance: 0.29mi , Attraction : Restaurant
Map Pin
524 Duval St, Key West, FL 33040, USA
POI 5 Tour Image
As you make your way down Duval Street, keep an eye out on the left side for one of Jimmy’s crowning achievements: the original Margaritaville restaurant. The first iteration of Margaritaville was a retail store opened in 1985 – more on that later – but Jimmy’s ability to merchandise his island vibes was growing quickly, and in 1987 the restaurant here on Duval was opened to the public.

Parrotheads love Jimmy for his music and the lifestyle it espouses, but Jimmy Buffett didn’t become one of the world’s richest musicians on record sales alone. Jimmy’s business acumen is notorious in the hospitality industry – the Margaritaville brand has grown to include resorts, casinos, hotels, and restaurants with locations all over the US, Canada, Mexico, several Caribbean islands, and even Sydney, Australia.

The Key West Margaritaville stands as a testament to Jimmy’s enduring spirit. The interior has been more or less unchanged from the eighties, including a bar shaped like a beach cabana and an upstairs dining area reminiscent of Buffet’s infamous front porch.

As for the menu? The Cafe serves plenty of delicious dishes, like conch fritters and volcano shrimp, but the most popular item by far is the Cheeseburger in Paradise, done up just like the song, with lettuce, tomatoes, and french-fried potatoes – The Heinz 57 is optional. You can pair your burger with a cold draft beer, or try that frozen concoction that gives the restaurant its name.

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Place #6
Distance: 0.15mi , Attraction : Historic Bar
Map Pin
208 Duval St #204, Key West, FL 33040, USA
POI 6 Tour Image
The Old Anchor Inn and Captain Tony's Saloon
Our next spot takes us back in time from Jimmy’s business empire days to his earliest years. The Old Anchor Inn is coming up on your left side, now going by the name of the Red Garter Saloon. The Red Garter is an adult entertainment spot now, but the Old Anchor wasn’t exactly family-friendly back in the day either.

The Old Anchor Inn was nicknamed “The Snake Pit” back in 1971 when a young Jimmy Buffett first arrived in Key West. Folks slept in their cars behind the bar and the restroom floors were always flooded. Patrons gambled the clothes off their backs and nicked replacements from local clotheslines. A line scrawled on the bathroom wall was used by Jimmy in his 1981 song “If I Could Just Get It on Paper”. The scrawled message read: ‘“Life and ink run out at the same time” – Squid’.

To a young Jimmy, this seedy establishment provided a source of inspiration and more than a few stories we can’t repeat in polite company. More than a few nights involved hasty escapes through the upstairs window, broken beer bottles, and plenty of expletives.

Turning right onto Greene Street, you’ll pass Captain Tony’s Saloon, another regular haunt of Jimmy’s from his busking days. Captain Tony’s still carries on the tradition that gave Jimmy his start, offering live music from local buskers.

Captain Tony’s is more than just a spot from Jimmy’s Past. The building was constructed in 1851 to serve as the town ice house and morgue. By the early 20th century, it had become a saloon; it was the original location of Sloppy Joe’s bar, now located just down the road. It’s been the favorite Key West watering hole of the likes of Ernest Hemingway, Truman Capote, Shel Silverstein, and of course, Jimmy Buffett.

Reportedly, it was in Captain Tony’s that Jimmy was offered his first major record deal. While Buffett had two studio albums under his belt from his Nashville days, he considers 1973’s A White Sportcoat and a Pink Crustacean to be his real first album. Jimmy was asked to record the album by ABC/Dunhill records after the tragic death of his friend and mentor Jim Croce. Though he had some pretty big shoes to fill, Jimmy stepped up to the plate and the rest is history.

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Place #7
Distance: 0.07mi , Attraction : Parking
Map Pin
410 Wall St, Key West, FL 33040, USA
POI 7 Tour Image
Parking Suggestion
From here on out, this tour becomes walkable. If you’d like to carry on on foot, feel free to stop the tour to look for parking. When you resume the tour, choose to begin at Starting Point 8. If you’d rather stay in the car, you don’t need to do a thing! Just follow the directions to the next spot.

Place #8
Distance: 0.11mi , Attraction : Landmark
Map Pin
Parking - Key West, 420 Wall St, Key West, FL 33040, USA
POI 8 Tour Image
Mallory Square
No tour of Key West is complete without a visit to Mallory Square. This historic plaza is home to one of Key West’s major attractions: the Sunset Celebration. Every night crowds gather in the square to watch the beautiful tropical sunset over the Gulf of Mexico. When the sun finally sinks over the horizon, everyone claps and cheers.

While much of Jimmy’s time as a young musician was spent singing in drinking establishments, Mallory Square was also an important location in his early days. Daytime busking in the square helped him get by in the leaner years before his music career took off.

Back in the ‘70s and early ‘80s, Mallory Square was much as it is today with upstart musicians, street vendors, and all sorts of rabble. The salt air was thick with the smell of incense, coconut, and less-than-legal tropical buds. As the sun sinks low in the sky, jugglers, unicyclists, and even trained jumping cats perform for tourists and locals alike.

The sculpture garden here contains an array of bronze busts of notable figures from Key West History. The 39 busts were crafted by sculptor James Mastin, and include such figures as Hemingway, Capote, and Tennessee Williams. Unfortunately, Mastin passed away in 2016, so the chances of a Jimmy Buffett bust being added are pretty slim.

Place #9
Distance: 0.06mi , Attraction : Historic Bar
Map Pin
0 Duval St, Key West, FL 33040, USA
POI 9 Tour Image
The Chart Room Cocktail Lounge
The Pier House Motel may have undergone some massive changes since the ‘70s, but the Chart Room cocktail lounge is still serving straight-up spirits like they always have. If you venture inside, be careful how you’re dressed! The ceiling of the chart room is hung with hundreds of neckties taken from patrons who dared ignore their casual atmosphere.

Reportedly, the Chart Room was the very first stop Jerry Jeff Walker made when he brought Jimmy to Key West. The bartender here was Tom Corcoran, a friend of Jerry Jeff’s known these days for his tropical-themed mystery novels. Corcoran would later help Jimmy write lyrics to “Fins” and “Cuban Crime of Passion”. Tom poured Jimmy a free beer to welcome him to the island, beginning a longtime friendship.

Jimmy would make the Chart Room his unofficial headquarters for several years. In the early days, he played for drinks here, entertaining the beachcombers, tourists, drug-runners, and divers that passed through the joint. Jimmy’s early audience would include journalist Hunter S. Thompson, singer-songwriter Jim Croce, and artist Vaughn Cochran, who would briefly play in Jimmy’s original Coral Reefer Band. The Chart Room was also the home base of treasure hunter Mel Fisher, famous for his 1973 discovery of 450 million dollars worth of gold and silver in the wreck of the Atocha.

The Chart Room is mentioned by name in Jimmy’s 1976 song “Cliches”. It is widely thought that “A Pirate Looks at 40” was written about a Chart Room bartender named Phil Clark. Phil was a drug smuggler with seedy connections all over the Caribbean, who would often stop through to drink at the bar. Legend has it that, when drowned in 1980, his ashes were snorted off the bar by his grief-stricken pirate friends. Whether or not this is true, it began an odd Chart Room tradition. Regulars have had spoonfuls of their remains embedded in holes in the mahogany bar itself, forever resting at their favorite watering hole.

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Place #10
Distance: 0.11mi , Attraction : Music History
Map Pin
422 Front St, Naval Air Station Key West, FL 33040, USA
POI 10 Tour Image
Howie's Lounge/Duval Village
Now a souvenir shop, Howie’s Lounge was where Jimmy found his first steady job as a musician. While his first indoor gig was at a nearby spot called “Crazy Ophelia’s,” Jimmy considers Howie’s to be his first real job. At the time, Jimmy was working on the Petticoat III. The job at Howie’s gave him the exposure he needed to make music his full-time career.

Howie’s Lounge only employed women to work as its servers and bartenders, which proved an effective tactic for packing the bar full every evening. The tiny stage was in the front window and was almost entirely occupied by a grand piano belonging to local legend “Coffee” Butler. Though most of the crowd was there to drink and ogle the staff, music lovers would fight each other for the chance to sit by the stage and hear Coffee play.

Jimmy played the cocktail hour, from five o’clock to eight every night. According to the man himself, he’d play all day, go raise hell at night, sleep a couple hours, then get up at four in the morning to catch fish. Of his time at Howie’s, Buffett would later remember thinking, “I have got this made. This is pretty cool!”

Howie’s is also the spot where Jimmy first met a lifelong friend, writer Thomas McGuane. Continue on to the next stop to learn more about their enduring relationship.

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Place #11
Distance: 0.15mi , Attraction : Music History
Map Pin
511 Greene St, Key West, FL 33040, USA
POI 11 Tour Image
123 Ann St/Captain's Corner Dive Shop
If you’re on foot, turn left to take a brief detour down Ann Street. On the right-hand side, you’ll see a small white and blue bungalow with a sign that reads “Captain’s Corner Dive Shop”.

Jimmy’s earliest residence on Key West was located here at 123 Ann Street, now the site of Captain’s Corner. The home was owned by Thomas McGuane, who had moved to Key West in 1970 with his first wife, Becky. Before Jimmy moved into his apartment on Waddell Avenue, he stayed here as a guest of the McGuanes.

McGuane and Buffett would go on to have a lasting friendship. It was Jimmy who gave Thomas the nickname “Captain Berserko”. As McGuane would later recount: Buffett was working very hard, and so was I. But on the weekends, Friday and Saturday nights, we really did kind of go nuts. My memory of the '70s is that was what everybody was doing on the weekends."

Following the popularity of his 1973 novel Ninety-two in the Shade, McGuane headed to Hollywood to break into the screenwriting business, and he dragged Jimmy along for the ride. His first film was 1975’s Rancho Deluxe, starring Jeff Bridges and Sam Waterston. Jimmy wrote the soundtrack for the movie; he and McGuane perform an alternate version of “Livingston Saturday Night” in a scene set in a Montana dive bar.

In 1977, after his divorce from Becky and a short marriage to actress Margaret Kidder, Thomas McGuane found the love of his life in Jimmy’s younger sister, Laurie. The two have been married ever since.

Head back over to Greene Street and take a left to continue on toward Shrimpboat Sound.

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Place #12
Distance: 0.29mi , Attraction : Recording Studio
Map Pin
200a Elizabeth St, Key West, FL 33040, USA
POI 12 Tour Image
Shrimpboat Sound Studio
Directly ahead, as Greene Street comes to its end, you can see a small white building on the water’s edge. Though this windowless structure looks unassuming, it houses Jimmy’s personal recording space: Shrimpboat Sound Studio.

Built inside an old shrimp storage shed, the studio is outfitted with state-of-the-art and antique recording equipment, including a pre-World War II microphone that Jimmy has used on many of his records. The studio was designed and outfitted by Ross Ritto, a longtime sound engineer on Buffett’s world tours. Ritto now owns Sound Image, an industry-leading sound design company.

Buffett and the Coral Reefer Band have recorded over a dozen albums in this little white building, including 1996’s Banana Wind and 2004’s License to Chill. Plenty of other artists have flocked to Shrimpboat Sound to soak up the Key West atmosphere and use Jimmy’s personal recording equipment. Country legends like George Strait and Kenney Chesney have used the space, as well as Alan Jackson, Toby Keith, and a host of musicians both famous and lesser-known.

The studio is fully soundproofed, but that doesn’t stop folks from pressing their ears to the wall in the hopes of hearing a hot new track from their favorite artists. If you’re on foot, head up Lazy Way behind the studio to get a closer look and check out the art and curio vendors that set up shop there.

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Place #13
Distance: 0.00mi , Attraction : Retail Store
Map Pin
280 Margaret St, Key West, FL 33040, USA
POI 13 Tour Image
Site of the Original Margaritaville/Local Color
All right, Parrotheads! This is the last stop on our journey through the island life of Jimmy Buffett. The yellow store you see here, now called Local Color, was once the site of the original Margaritaville retail store. Opened in 1985, it wasn’t around for long – the retail store moved to Duval street when the restaurant opened in 1987.

As I mentioned before, merchandising has been instrumental in Jimmy’s rise to fame. By the early ’80s, Jimmy understood the power of attaching products to his already massive personal brand. A contract with Corona beer in 1984 helped popularize the beverage in the U.S., and their partnership extended well into the ‘90s. A Corona ad that read “Change your Latitude” secured its spot as the number one beer in America, and Jimmy cashed in big-time.

The Margaritaville brand is synonymous with Jimmy, and will likely be as much a part of his legacy as his music. From frozen concoction machines to apparel, from boogie boards and cornhole sets to a whole line of alcoholic beverages, few retailers have a lock on the spirit of island life like Jimmy. And to think, that merch empire all started right here in that little yellow store.

Well, folks, that just about wraps up my time showing you around! I hope you’ve enjoyed this peek into the life of one of the world’s most influential musical artists. Since you’re in the neighborhood, check out Half Shell Raw Bar across the street, one of the island’s most popular spots for drinks and fresh seafood.

I hope today’s journey has given you yet another reason to love America’s Caribbean paradise. If you’re interested in making this change in latitude a little more permanent, give Tyler Sheff a call at 305-222-7081 or visit keywestrealtor.com to schedule a consultation. Until next time, this is Stephen from UCPlaces wishing you a fond farewell.

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