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  • Writer's pictureThe Traveling Locals

Key West, Paradise at the End of A1A

Updated: Nov 9, 2020

Smathers Beach Key West Palm Tree

The A1A south highway winds from Miami across tropical islands and over bridges spanning turquoise channels, and at the end of the palm tree lined road, you’ll find Key West. Cayo Hueso (Key West’s original name) has always been a special place for me, and for many reasons. It was the first “exotic” destination I had ever been, and my fist experience with the tropics. Almost 20 years old, I jumped on a cruise ship from Miami on a last-minute invitation with a group of girls I barely knew from one of the stores I worked near. After a night on the ship, I woke up in port at Mallory Square and after seeing the azure turquoise Caribbean waters and coconut palms I was hooked. I didn’t spend much time in Key West that day, just a brief catamaran and snorkel excursion arranged by the cruise line. But that day changed my life forever and I didn't wait much longer to return to the “Southernmost” place in the United States. I jumped into my car less than a month later and drove the 12 hours from Charleston straight to Key West! This is where I fell in love with the unique conch culture of the place. I've since been back probably close to a hundred times! While it is absolutely a tropical island in the Caribbean , that’s maybe not why people just pack up and move there. Maybe it’s the culture of people that don’t really fit in anywhere else, but somehow seem to all be in the right place perched at a local bar under a tropical tree. Maybe it’s the eclectic mix of unique characters performing street tricks at sunset on the pier. Maybe it’s the “Margaritaville” culture and the ghosts of Jimmy Buffett’s good times still in the atmosphere. Maybe it’s all of the above. Maybe I should just get another drink in paradise.

Smathers Beach, Key West travel
Smathers Beach, Key West

Countless visitors flock to Key West every year by planes, cruises, automobiles, boats and ferries. And if you are reading this, you are probably soon to be one of them. I mean, who doesn't love topical weather all year round, especially if it's January?

Key West is a very fun place to be, and it can be as "fun" as you want it to be. The cool thing about this destination is it is a kind of build your own. There is something for everyone, whether you are a family, bachelor and bachelorette parties, long weekends in a unique setting, outdoors enthusiasts, historians and people looking for a serious good time. Remember Key West has a lot of drunken debauchery if you know where to look for it, but if you want nothing to do with it, it's not hard to stay avoid it either (at least during certain times of the year).

Sailboat at Sunset Mallory Square, Key West travel
Sunset from Mallory Square, Key West


KW has several beaches, but isn't really a traditional beach destination. Most of the water around Key West is best enjoyed on a boat or in the water. However, any beach in Key West is still better than a day of work, every time. The largest is Smathers beach near the airport, and here you'll find white sand and shallow water with plenty of options for water sports. The next largest beach is in Fort Zachary Taylor state park, and here you'll find a small shark for food and drinks along with showers. There are many smaller beaches around the island, mostly near the White Street pier, Higgs beach and in front of west Martello tower are popular. Be careful, while not official, nudity is not shunned upon in KW and you'll often find people in various states of undress at some of the smaller beaches. If you are looking for a family friendly beach then look no further than Zachary Taylor Park.

Zachary Taylor State Park Beach Key West Travel
Zachary Taylor State Park Beach

Fort Zachary Taylor

There is a small entrance fee, but there is always tons of parking and on calm days, the beach is very nice. There is a concession stand selling snacks and alcohol. Showers and bathrooms are on site. Included in the entrance fee is admission to the fort itself. Construction of the fort started in 1845 and was a key Union position during the civil war. It was actually still in use all the way up to 1947! Today you can wander through most areas and explore the different rooms and tunnels, as well as scenic walkways around the impressive moat.

Inside Zachary Taylor Fort, Key West florida

There is also a smaller "hidden beach in Zachary Taylor park after a short walk along the breakwater to the right. The beach here is white sand, clear and calm.

Secret Beach Zachary Taylor Park
The "Hidden" beach to the right of Zachary Taylor


The Botanical Gardens and Key West Garden Club are absolutely beautiful. They have a lot of very beautiful tropical plants to admire and snap pictures of. Unfortunately, Hurricane Maria did some damage, especially to the West Martello Garden Club, and they are doing what they can to regrow what was lost. But it is still beautiful.

Flower Key West Garden Club

Southern Most Point

Plenty of tourist find their way to this iconic landmark, and you will probably have to wait in line with them to capture your picture next to it. But to give you a little insight, it isn't actually the Southern Most Point at all. The most southern point of KW and the east coast is really a mile or two down the road on military property. Obviously because of where it is located, it is off limits and you can't get to it. So for looks, they put the large painted buoy like attraction where it is. It is still fun to go have your picture taken with it, and the truth that you stood in line with a bunch of other tourists and cruise ship passengers will be our little secret.

The Southernmost Point, Key West
The Southernmost Point, Key West

The Zero Mile Marker

US1 is the longest road going from the North to South in the United States. It starts in Maine, at the border of Canada, and runs all the way down to Florida, ending in Key West. Which is what makes this sign so famous. So make sure to get your camera out and take a selfie with it. And there is a tons of memorabilia shops close by on Duval Street for you to pick up and take home. Bumper stickers and all.

The Hemingway House

Photos and stories fill everywhere you go in KW. Earnest Hemingway was larger than life figure, and he lived here in KW from 1931-1939. He wrote Death in The Afternoon, The Green Hills of Africa, The Snows of Kilimanjaro, and To Have and Have Not all while living in this home. The house is filled with the decedents of Hemingway's six toed cats, making this a unique experience. As you are walking around the outside grounds, make sure to look in the concrete surrounding the pool and locate the "penny tile". After seeing the insane amount of money his wife spent on the pool, Hemingway is famously rumored to have thrown the penny down and said "Pauline, you’ve spent all but my last penny, so you might as well have that too!" The 1934 penny is still there on the side of the pool today. Pretty funny, right?

Hemingway House Key West Travel
Hemingway's House

Hemingway's six toed cat
Hemingway's six toed cat

Besides writing and fishing while in KW, Hemingway's other favorite past time was drinking and socializing. His favorite spot on the island was the original Sloppy Joes Bar, now called Captain Tony's saloon. If you can stand under the stuffed Goliath grouper and toss a quarter over your back and into the fishes mouth, good luck will follow you for your time on the island. It took me years to finally make it, but I've seen many a tipsy tourist sink it on the first try. Captain Tony's is one of the most unique waterholes in KW. During it's history, it's been a morgue, and ice house, telegraph station and several speakeasy's and brothels. The namesake, Captain Tony Tarracino was once the mayor of Key West and was an immensely colorful character in his own right. Jimmy Buffett got his start here, and his song lyrics are immortalized on the wall of the men's room. There are also a couple grave markers withing the bar where some of Key West's former residents are buried. And look for the skeleton propped up behind the bar, rumor is, this is a real skeleton from a body that was never claimed long ago during the bars time as the city morgue.

Captain Tony's Saloon Key West Travel
Captain Tony's Saloon Key West

No trip to Key West is complete without a visit to Duval Street in Old Town. Here you'll find many bars, live music, shops and restaurants. Sloppy Joe's Bar on Duval and Greene street is an institution in KW and usually feature live music. Irish Kevins is just a couple steps away with interactive musical acts geared for a more adult audience with drinking games and hilarious sing alongs. My personal favorite is the Tree Bar (part of Dirty Harry's). It's a small open air corner bar with a large tree growing at the corner and it's a great place to sit, have a beer and watch the chaos out on the street.

Sloppy Joe's Bar Key West

There are a lot of other unique venues within close walking distance of Duval Street to satisfy pretty much anything you're looking for. The Bull and Whistle bar usually has local music playing downstairs and billiards on the second floor. Stroll up the main stairs or take the back staircase and you'll find a bar like no other down on Duval street. Once you walk into the Garden of Eden, you'll probably be shocked to find lots of people in various states of nudity dancing this rooftop bar. It's pretty much what you'd imagine from a clothing optional bar, most the partake in the nudity, probably shouldn't. But everyone is in on the joke and it's a hilarious experience, especially when drunken tourists decide to join the fray and lose their clothing along with inhibitions.

The Bull and Whistle bar Duval Street Key West

Garden of Eden Clothing Optional Bar Key West

You'll find a mix of plenty of additional bars and restaurant away from Duval street as well.try spending a great afternoon drinking a cold beer at the locals geared Green Parrot on Whitehead Street.

You cant' go wrong with some of our favorite restaurants in Key West: Blue Heaven, Hogfish Bar & Grill and Garbo's Grill. Blue Heaven has both indoor and outdoor seating and is amazing for fresh seafood, dinner and brunch (no one is awake in Key West in time for breakfast). Hogfish is actually on Stock Island, located in a marina frequented by manatees. There is usually a mix of locals and tourists enjoying cold drinks and great food. Try the smoked fish dip and the grouper cheeks with key lime relish.

Manatees in Key West

Garbo's Grill is actually a food truck on Caroline St makes the best Korean BBQ tacos, mango chili hot dogs and umami burgers. Outside of fast food places on the island, this is probably the best priced meal you have in KW.

Garbo's Grill Food Truck

Key West has many other sights and activities to experience and is well worth a visit. Kayaking, boating, snorkeling, scuba and fishing are immensely popular. Strolling through the history of KW's cemetery and finding some of the hilarious tombstones is a great insight into the local Conch culture. You may find yourself on the island during one of the many, many festivals and event's like Fantasy Fest, Songwriters Festival or Hemingway Days. Just make sure to plan head, grab a cold drink and blend into the Saltwater Conch culture. Enjoy.

White Ibis Birds Key West

Where We Stay: Crowne Plaza ((La Concha) Duval Street), The Saint Hotel (Eaton St), The Reach (Simonton st), Hilton Garden Inn (Roosevelt blvd), & lots of private hotels/BnB's.

Where We Eat: Blue Heaven (Petronia St), Garbo's Grill (Carolina St), Hogfish Bar & Grill (Stock Island), Satiago's Bodega (Petronia St), Alonzo's Oyster Bar (Front St), The Waterfront Brewery (William St), Geiger Key Marina (Geiger Key), Better Than Sex (Adult themed desserts! Truman Ave).

Where We Drink: The Tree Bar & Dirty Harry's (Duval St), Irish Kevin's (Duval Street), Sloppy Joe's (Duval Street), Hogs Breath Saloon (Front St), The Green Parrot (Whitehead St), Southernmost Cafe (Simonton St), Shot's and Giggles (Ann St), Smallest Bar in Key West (Duval St), Captain Tony's Saloon (Greene St), Bull & Whistle/Garden of Eden (Duval St)

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