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Key West Hop-on Hop-off Trolley Tour
"Explore Key West while hopping on and off at any of our designated trolley sightseeing stops. Visit over 50 points of interest with this all day pass as our expert guides provide live narration and entertainment with stories only locals could tell! Audubon House) LaConcha Hotel (Margaritaville Oldest House Museum) Florida Keys Eco-Discovery Center (Fort Zachary Taylor State Park U.S.S Mohawk) Higgs Beach (White Street Fishing Pier West Martello Tower) Southernmost Point (Southernmost House Mansion Upper Duval Street Shopping) Ernest Hemingway House Museum (Lighthouse Museum Bahama Village) Key West Bight (Schooner Wharf
From $20.00
Key West Day Tour from Miami
"The Key West Tour from Miami includes hotel pick-up. Hotel pick-up times may vary from 5:45 am to 7:00 am depending on location. This tour includes round-trip transportation from Miami to Key West. The bus tour to Key West is a great way to enjoy th the road popularly referred to as the Overseas Highway. This 125-mile road trip stretch the crystalline emerald waters and lush tropical landscapes of the Florida Keys. And with so much to see and do en route you consider this to be the nation’s most charming routes. The US Highway begins with mile marker zero in the central location of Old Town Key West and runs north towards Miami. While you take in the sights while driving to Key West you can explore both populated and deserted land including the well known Seven Mile Bridge. About Key West: Key West a petite island city is a viable part of the Florida Keys and the state's southernmost pinnacle. Located approximately 90 miles north of Cuba
From $49.00
Key West Ghost Walking Tour
"Florida’s Key West has a history full of pirates wreckers smugglers and other sinister characters. On this nighttime ghost walking tour explore Key West’s haunted side with your expert guide and prepare to be spooked! As you wander down dimly lit streets and eerie alleys listen as your guide tells first-hand stories and legends of Key West's most infamous haunted places. Learn of ghosts and ghouls as you visit the Hard Rock Cafe Banyan Resort Eaton Lodge
From $21.00

Capt. Tony's Tips (9)

Capt. Tony's: Original Hemingway Hangout

This is the original site of Hemingway's Sloppy Joe so it is only fitting that this is the first bar my now husband, Joe, dragged me to in Key West. In its earliest incarnation (1851), Capt. Tony's Saloon was a morgue and icehouse, then Key West's first telegraph station. It was also a cigar factory and a bordello before it became the original Sloppy Joe's in the mid-1930s (when Hemingway was a regular). Later, a young Jimmy Buffett sang here (he wrote his song Last Mango in Paris about it).

It is your basic, dark dive bar where people have put up their business cards and some have left other memorabilia (i.e. license plates and bras). They serve lots of beer and great rumrunners. They do NOT serve food here. In addition to the patron decorations, there is a bust of Hemingway, and a single photo of the author of The Old Man and the Sea fishing with Tony Tarracino, a onetime mayor and former owner.

Dress Code Last Mango in Paris lyrics by Jimmy Buffett:

"I went down to Captain Tony's
To get out of the heat
I heard a voice call out to me
Son come have a seat
I had to search my memories
As I looked into those eyes
Our lives change like the weather
But a legend never dies"

TRimer's Profile Photo
Jul 25, 2007

Capt. Tony's Saloon: Hemingway's "Sloppy Joe's" & Hanging Tree

Came here as part of a "pre-wedding" party - and it was FUN! Live band was playing at the front; we sat toward the back, by the tree growing through the bar's ceiling! I was told later that this was Key West's "hanging tree", and that 75 people were hung from it! On the ceiling were hundreds of license plates from around the country, hundreds of brassieres (most signed), and thousands of business cards. It made it fun to stare at the ceiling, and made for some hilarious "bachelor party" type photos...

TravellerMel's Profile Photo
Mar 11, 2011

Capt. Tony's: historic bar

captain tony's saloon is located in a 1851 historic building on greene street. this bar was originally named russell's in 1933. ernest hemingway convinced the owner joe russell to rename the bar sloppy joe's because joe "ran such a sloppy place". in 1937 russell had a disagreement with his landlord and moved the bar to duval street. today this historic bar is called capt. tony's saloon. capt. tony's is a fun place to drink and soak up old keys atmosphere.

Dress Code casual.

doug48's Profile Photo
Nov 05, 2008

Capt. Tony's: Local Institution

Captain Tony's is an institution in Key West. It features a bar, food and live music. It been featured in many books and songs, including some famous jimmy buffet references. A must see when here for its iconic status.

Jim_Eliason's Profile Photo
Mar 11, 2016
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Capt. Tony's: Deserted

We were headed to Captain Tony's after hearing stories about it in Hemmingway lore.
However, when we arrived, the place was quiet and practically deserted. The bras were all still hanging from the ceiling though.

Dress Code Very, very casual

sunloverinatlanta's Profile Photo
May 12, 2009

Capt. Tony's: Capt Tony's - Duval Street, Key West

We stopped at Capt Tony's between visits to Hogs Breath and Sloppy Joe's. Capt Tony's is more divey than either, but also kind of a happy medium between the touristyness of Hogs Breath and the raunchiness of Sloppy Joe's. Good place to stop in to listen to live music, play foosball, or watch sports, but not a good place to bring your kids. We had a few Red Stripes, because their brew selection was pretty limited.

This bar brags that from 1933 to 1937 it was not only the original location of Sloppy Joes, but it was also Hemingway's hangout while he lived here during the same time period. In fact, Earnest Hemingway liked this bar so much, when it was remodeled, he acquired one of the old urinals and installed it as a fountain at his home a few blocks away.

Ewingjr98's Profile Photo
Sep 02, 2012

Capt. Tony's: GREAT PLACE

Came here as part of a "pre-wedding" party - and it was FUN! Live band was playing at the front; we sat toward the back, by the tree growing through the bar's ceiling! I was told later that this was Key West's "hanging tree", and that 75 people were hung from it! On the ceiling were hundreds of license plates from around the country, hundreds of brassieres (most signed), and thousands of business cards. It made it fun to stare at the ceiling, and made for some hilarious "bachelor party" type photos

Jun 24, 2012

Captain Tony's: Discover the true flavor of Key West

Captain Tony's is a must see and is after all- the original site of Sloppy Joe's. This Old Town Key West Bar is an authentic place; Dark, dank, humid salted air with a stale beer smell. Built in 1852 Capt. Tony’s is the oldest bar in Key West. Hemingway spend many time here between 1933 and 1937. Today the walls are decorated with underwear and the ceiling with thousands of business cards of customers who have put on the ceiling through the years. Check out Hemingway's original bar stool and his "hanging tree" (it grows through the roof).

If your looking for a fancy bar, go somewhere else!

Dress Code What dresscode..........we're on Key West!!

Dutchnatasja's Profile Photo
Oct 28, 2005

Top 5 Key West Writers

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"The Parents of a "
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"key west florida"
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"Key West, Florida"
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"Key West Driving Trip May 3-12, 2003"
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"Key West one of my favorite spots in North America"
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Capt. Tony's & The Green Parrot: My two favorites...

While similar in many ways, two nightlife extreme opposites are Capt. Tony's Saloon and The Green Parrot. Capt. Tony's is where that Jimmy Buffett guy went to get out of the heat, and it has a funky, almost cave-like, atmosphere where you will very likely hear some local Buffett wannabe playing guitar and singing. Unfortunately, this is one of those places the "tourists" just have to see, so the best time to go is in the afternoon while they are all shopping for T-shirts.

Dress Code The Green Parrot, on the other hand, is strictly a "locals" type bar and what is known as a "Buffett-free Zone". No Jimmy on the jukebox here (and whatever you do, don't ask for Buffett). "The Parrot" does, however, provide some of the best "Blues" in the Keys. Both local and imported talent poor their hearts out onstage at "The Parrot" on a regular basis. Try to get Vicky, the bartender, to sing for you. She is incredible (at both singing and tending bar).

KeyWest6's Profile Photo
Feb 06, 2003

Things to Do Near Key West

Things to Do

Duval Street

Galleries, shops, bars and big beautiful homes with huge porches. Key West is a small island city with a very diverse population. It's a wealthy community, with plenty of regulars just trying to make...
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Things to Do

West Martello Tower

When we lived in Key West there in the late 60s, they hosted a flower show in the winter. If you go at the time of the flower show they have some amazing flowers that you can see in addition to the...
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Things to Do

St. Mary's Star of the Sea Catholic Church

Saint Mary Star of the Sea was established in 1851, making it the oldest Catholic parish in Key West and the fifth oldest in the state. The present church was completed in 1905 (the first church was...
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Things to Do


On the grounds of Hemingway House is a unique cemetery for the six toed cats that live there. Hemingway named his cats after famous people, and that tradition has continued - as can be seen by reading...
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Things to Do

Butterfly Conservatory

Before we cruised to Key West, I had done a lot of research about what to see. I fell in love online with the Key West Butterfly Conservatory. It was our first stop in Key West (CityView Trolley...
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Things to Do

Southernmost Point

It's free and easy to find .. and a must do if your there. . We have only been there twice and don't know that we will return but it was a lot of fun. a party place year round. After that you have to...
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Getting to Key West


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