Everything You Need To Know About Key West: Where To Stay, Getting Around, Local Customs & Its Characters
There’s more to Key West than Duval Street, legendary bars and spectacular sunsets. Getting to know the Conch Republic means understanding its laid-back attitude, colorful characters, local customs and unique island lifestyle. This complete orientation guide covers where to stay, how to get around, what to expect and what makes Key West unlike anywhere else. This article was last updated in November 2026.
By Kevin Wilkerson, PubClub.com Editor & Publisher
Prior to soaking in its sun, here’s what to expect regarding attitudes (very important here), customs, transportation, weather and more in Key West.
Key West Myths, Legends & The Laid-Back Island Lifestyle
It can’t be true, some say, that Key West is as laid-back as people claim it to be.
Let’s just put it this way: no one will ever confuse it with New York City.
If Key West seems part fiction and part reality, well, just remember that Ernest Hemingway once lived here. And just about everything or everybody here has some type of story to tell, be it myth, fact or just good ‘ol legend.
The pace here is slow. So slow, in fact, it sometimes makes a place like Jamaica seem as it’s moving at the speed of a bobsled by comparison.
Warning: It’s a pretty contagious lifestyle. That’s why some people contact “Keys Disease” and never leave.
Key West is a never-ending carnival. Its sunsets on Mallory Square are daily rituals that bring out all the town’s colors. As well as its colorful characters – clowns to high-wire artists to a human statue. This is, after all, a town that once featured a weekly column by a dog, Reggie, in one of its newspapers.
This makes Key West very much like Amsterdam in that it has a very liberal attitude toward the people who visit and live here. Any lifestyle – be it gay, straight, eclectic, private or public – and any person – be they celebrities or ordinary folk, has-beens or never-want-to-be’s – are all accepted on equal terms.
Where To Stay In Key West: Duval Street, Old Town & Lodging Tips
Key West is part of the chain of tiny islands south of Miami called the Florida Keys. It was first settled in the 1820s and quickly became a home for mariners, a hangout for artists and a hideaway for people looking to escape their past. Some things haven’t changed to this day.
The first thing a visitor should do upon arriving in Key West is to take off one’s watch.
The second thing a visitor should do upon arriving in Key West is to take off one’s shoes.
There are two most unnecessary items in Key West for residents and travelers: It doesn’t really matter what time it is and sandals are the widely accepted footwear. There is hardly a dress code for Key West; even the finest restaurants welcome people with shorts and t-shirts.
Many of the t-shirts sold on Duval Street are typically touristy tacky. But once the wardrobe issue is settled, it’s time to take the car back to the rental car agency or, for those who arrive in their own wheels, finding a shady place to park for the duration of the visit. The entire town can be walked in a mere half-hour, and that’s from one end to the other. Most of the activity occurs on the North end of Duval Street making it the most convenient location to stay. Not surprisingly, it’s also the most expensive.
Duval Street is the main – and to some the only – street in Key West. It is on this primary path that Key West’s heart beats the loudest. Most of the tourists gather from the 200-block to the end, lured off the street by stores, art galleries, the town’s most popular bars and enough t-shirt shops to outfit the entire Eastern Seaboard.
Front Street, Greene Street and Caroline Street – watch out for that woman goin’ crazy! – all bump into Duval at its lower end. Mallory Square, scene of the world’s most entertaining sunset ritual, is next to the Cruise Ship Port just past Duval and Front streets.
There are a number of accommodations options in Key West ranging from chain hotels to small family-run motels. As mentioned above, the prices increase the farther north one strays on Duval Street, from $150+ a night to more than $300.
Speaking of prices, except for the t-shirts, this is not a cheap town. In addition to the cost of your room, there is the volume at which you consume drinks, so fully enjoying Key West can be a pricey, though fun, adventure.
Getting Around Key West: Walking, Bicycles & Transportation
The easiest way to move about Key West is on foot. The main part of town is tiny enough to walk with ease.
As saving human energy is one of the prime activities on Key West, many use mopeds to scoot about town. Bicycles are also available for rent.
The Conch Train is kind of like that vehicle in an amusement park that takes you from your car to the entrance and it’s pulled by a “train” with a tour guide (be sure and tip!). It’s a good way to reach the outer parts of Key West, including the Southernmost Point (and Louie’s Backyard) and the Harry S. Truman Little White House.
Key West’s History Of Colorful Locals And Legendary Characters
Go for a weekend and experience what the tourists see. Stay a little longer and learn about the unique characters that call Key West home. Key West has a history of colorful characters and the tales they tell may or may not be true. Some are still around and some are not but one thing is for sure: you will encounter all kinds of interesting characters in Key West.
For a long time there Captain Tony Taracino, owner of a saloon who was once voted mayor when his patrons got fed up with the town’s politicians. Uncle Albert, a former black-belt who claims to have once fought Chuck Norris, would watch your illegally-parked moped for a buck to be sure it isn’t ticketed. His trusty sidekick was Little Joe, an underwater construction worker.
There is the guitar-playing Fritz, who performs at various bars about town. And singer Robert, part of the cleaning crew at Sloppy Joe’s who one afternoon a few years ago got on stage with Fritz and was so good, locals demanded he join the band (he did, yet he still cleans up at Sloppy Joe’s).
Band leader Michael McCloud is as content as they come. He is what Jimmy Buffett would have become had Buffett not got tired of swimming in this roped-off sea and headed for bigger waters.
Gabby is a human statute, one of the many creative characters that come out at sunset on Mallory Square.
There is a lovely waitress who has been working here since after high school who is content to keep serving conch fritters and beer well into her golden years and and a pair of French girls who run a smoothy stand on Duval Street and Captain Nick of the Key West Police Department. Suffice to say that if we include the name of a police captain on PubClub.com, then he must be one cool dude.
Countless bartenders, waitresses, vendors, shop-owners and street performers all have made Key West their home Visitors who stay for longer than a three-day weekend are encouraged to do the same.
Key West Bars, Nightlife & Local Drinking Customs
Life in Key West revolves around its many bars. Often, it’s so hot and lazy that people head for the bars in the afternoon just to escape the heat.
Most bars have an old-time nautical feel about them. Dark wood walls, bamboo ceiling fans and large windows that can open up to the outside giving one a sense of Key West’s maritime history.
Every place in town features live music. Generally speaking, the music quality increases with the passing hours, reaching a peak in the evening. Most places have Happy Hours from 4-7 p.m., with special drink prices.
There are usually no cover charges and crowds are largely comprised of weekend warriors from South Florida who come down by the car loads for two days of escapism and revelry. They mix in with visitors from other Southern and Eastern states in the U.S., and a sprinkling of European tourists. Most of the latter are vacationing in South Florida and simply make Key West a stop on their itinerary.
This is no South Beach and it’s hardly crawling with single people on the love prowl (two of the exceptions being Spring Break and Halloween). What you will find instead is a very friendly party crowd that gives Key West honest hospitality.
It’s legal to have a drink on the streets, but in plastic cups only. Captain Nick and his staff frown on bottles.
Drink ’em if you got ’em in the bars is 1 or 2 a.m.; clubs stay open until 4 a.m.
Jimmy Buffett’s Key West: Where Margaritaville Began
He first arrived nearly cashless in 1971 with a friend named Jerry Jeff Walker. It is here that he developed his style of songwriting based on living the fantasy beach life. He played and drank in the small bars around town and it was here that he created the mythical tropical paradise that became Margaritaville.
Jimmy Buffett pretty much put Key West on the tourism map. It’s where he first performed “Margaritaville,” at the Chart House. He finished it while stuck in traffic on the Seven Mile Bridge and when people asked him to play it again, he realized people liked it.
“I lived in Key West for three years and mostly all I did was hang out in bars,” he once wrote. He’s got a restaurant/bar/store here, Jimmy Buffett’s Margaritaville Cafe. The margaritas aren’t the best in town. But Parrotheads do love the gift shop.
Give Buffett credit for bringing Key West much of its tourism, more than other famous occupants Hemingway, Harry Truman and Tennessee Williams, but his popularity is largely lost on those who live here. Locals musicians, often swamped for requests from tourists, often refuse to play Buffett covers on their own.
Still, it’s hard to come to Key West and not feel the spirit of Buffett. It’s even easier, however, to understand how Key West provided the inspiration for his music and tales from Margaritaville.
Key West Time Zone
Key West is in the Eastern Time zone.
Best Time To Visit Key West: Weather, Festivals & Events
October thru March is Key West’s high season. The town hosts some type of festival about once month. Fantasy Fest (late October) is a 10-day celebration featuring wild costumes and wilder participants, is the largest of them all; finding a hotel room during this time is virtually impossible. The Hemingway Days festival (early July) is also wildly popular. Spring Break (March) fills Key West with college students from all over the South.
New Year’s Eve in Key West is something that should be on every PubClubber’s bucket list.
Summers are extremely hot and humid, providing for good inspiration to visit the many air-conditions bars in the afternoon.
Key West Q&A
Do you need a rental car in Key West?
No. If you have a car in Key West, will stay parked during your visit.
Where is the best area to stay in Key West for nightlife?
As close to the end of Duval Street as possible
What is the best time of year to visit Key West?
For events, the pubs and clubs are busiest in the winter, for Spring Break and for big events like Fantasy Fest and New Year’s Eve. Summers are hot and slow.
Can you walk around Key West easily?
In the main areas, yes. The Southernmost Point landmark is not walkable from Duval Street but 95% of where you will be in Key West is only about a 10-15 minute walk at the most.
Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and nightlife for more than two decades. While working as a newspaper reporter, he received an Associated Press award for investigative journalism. He has been to Key West several times.
Next Stops On The Key West Party Bus:
• The Nightlife Blogger In Key West!
• The Nightly Ritual Of Mallory Square Sunsets
• Oh My Gosh, I’ve Got Keys Disease!
PubClub.com covers nightlife, bars, festivals and party events around the world. I have been to Key West many times.