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Key West—the last outpost of the Florida Keys.
Home of the original Key Lime Pie, home to roosters that roam free, and also once home to Ernest Hemingway who had a tendency to roam free as well.
Key West is connected to the mainland U.S. by forty-two bridges. The Overseas Highway, completed in 1938, is an iconic (or terrifying if you don’t like driving over water) roadway spanning 113 miles. The Seven Mile Bridge, aptly named for its length and scenic views, is the longest bridge along the highway.
Key West is a small island, making it easily walkable. The island is only about four miles long and two miles across at its widest, with the popular Old Town making up approximately half of this area.
The best months to visit Key West are typically between December through May with the “wet season” coinciding with hurricane season during the months of June through November. During the winter months, the temperatures only drop to the mid-60s.
Although Key West can be touristy in places, it remains a beautiful and interesting island paradise once you get past the cookie-cutter T-shirt shops selling rooster coffee mugs.
Whether you want to spend your time in Key West immersing yourself in the history and laid-back culture of the island or just relax on the beach after a day on the water, you can’t go wrong.
Looking for a beautiful place to stay in Key West? Click here for the top VRBO rentals.
Walk Duval Street
Spanning a little over a mile, a stroll down Duval Street is a walk through Key West’s history. Along this street, you’ll find loads of restaurants, bars, eclectic shops, quirky art stores, and beautiful homes showcasing Victorian-style mansions with Bahamian and Cuban influence.
If you start your walk at the north end of Duval Street, near Mallory Square and the cruise ship docks, one of the first iconic establishments you’ll come across on your walk down Duval is Sloppy Joe’s.
Sloppy Joe’s
Opened in 1933 and originally named “The Blind Pig” and then “The Silver Slipper,” Ernest Hemingway encouraged the bar’s final name change to Sloppy Joe’s. The new name was in reference to a Havana club run by Jose Garcia that sold liquor and iced seafood. Since the floor was always wet with melted ice, it wasn’t long before patrons started calling it “Sloppy Joe’s.” The name stuck and Hemingway thought it was the perfect fit for this Key West bar.
You can order a “Sloppy Joe” sandwich here or choose from other indulgent menu items like pizza, nachos, or tacos. There’s only one dessert on the menu though, and that is, of course, key lime pie. The drink menu is loaded, and you will be too if you stay here drinking too long.
Duval Street Architecture
Walking Duval Street is also a fun way to enjoy the best of Key West’s architecture and historic homes.
Key West features several different home styles, but one of the most iconic is the Conch Style—homes featuring two stories, wraparound verandas, and shuttered doors and windows. Many of these houses are accented with vibrant hues like turquoise shutters or pink foundations.
The more ornate homes in Key West are designated as Queen Anne homes, or “late Victorian” homes. These are easy to spot. Look for steep gabled roofs, lacy woodwork, and maybe even a turret or two.
St Paul’s Episcopal Church is also located along Duval Street and features a Gothic Revival style.
The church had to be rebuilt 4 times between the 1830s and 1919 due to hurricanes and fires. After several renovations, the church is open daily for visitation, prayer, and meditation, with its large collection of stained glass windows being of particular note.
Duval Street Restaurants
In addition to the historic Sloppy Joe’s, Duval Street is also home to several restaurants and cafes.
If you love a good brunch and want to dine in one of Key West’s historic homes, then you’re in luck. Bagatelle Island Restaurant serves brunch daily from 9:00 am to 4:00 pm with dinner service starting at 5:00.
The house was built in the 1800s but was converted into a restaurant in 1979. In true Key West style, Bagatelle offers two Happy Hours.
The first is a breakfast hangover happy hour from 9-11:30 am daily, highlighting a tapas, small-plate style breakfast. The afternoon happy hour is from 4-6 pm daily at the bar, offering $5 tasting plates and half-off most cocktails.
The Key West Butterfly and Nature Conservatory
Conveniently located on Duval Street (near the Southern end), the Key West Butterfly and Nature Conservatory is a remarkable experience. It is one of the best things to do in Key West and is definitely worth at least 1 hour of your time.
Due to the popularity of this Key West attraction, you may have to wait in line for your tickets, but once inside the conservatory, you are free to take your time as you make your way through the winding paths brimming with tropical flowering plants, waterfalls, birds, and what the conservatory refers to as “the flowers of the sky.”
Butterflies flutter all around you, and while the Blue Morphos were the most eye-catching, the conservatory features 50 – 60 different species of butterflies from around the world.
The Key West Butterfly and Nature Conservatory is also home to two incredibly pink (and vocal) Caribbean Flamingoes named Rhett and Scarlett.
Rhett and Scarlett were rescued from a breeding facility and have been living a posh Key West life at the conservatory ever since.
Caribbean flamingoes typically live 20 – 30 years in the wild but can reach 60 years old when they live in a preservation facility like the Butterfly Conservatory.
In addition to the pink flamingoes, there are several other tropical bird species to spot inside the glass-enclosed conservatory. I almost mistook this green Turaco for a statue when I walked past him perched on a ledge as I was getting ready to exit the convervatory.
Before or after your visit, be sure to take a moment to explore the large gift shop featuring all sorts of butterfly-themed art and gifts.
One key feature of your ticket is that you can return on the same day and re-tour the conservatory for no additional cost. This is especially helpful if when you first toured the facility was crowded or maybe you just want to come back by and cool off after walking around Key West.
If you’re interested in visiting the Key West Butterfly and Nature Conservatory, click this link or the button below for up-to-date hours and ticket information.
The Southernmost Point of the Continental U. S. Buoy
I’m not sure if this one qualifies as “fun” or not, but it’s a popular spot and worth a mention, especially after you’ve taken a walk down Duval Street or Whitehead Street (where the Hemingway Home is located).
While there’s really not much to do at the Southernmost Point Buoy except look at the monument and take a picture, it is a popular tourist attraction for that very reason. When you stand next to this buoy, you’re closer to Cuba than Miami. Everyone wants to have a photo documenting their visit there, and a line will form along the sidewalk leading up to it.
I’m not for breaking in line, but I’m also not for wasting my precious time in Key West waiting to have my photo taken by a buoy. If there is a line, and you don’t want to wait, my suggestion is to position yourself on the street curb near the iconic Buoy and snap a shot with the landmark in the background in between the tourists as they come and go in the “official” line.
When I got the photo above, it was pure luck that I got there before a huge group of people began lining up to get their photographs. If you don’t care to have your picture made by the marker but want to enjoy the ocean views from that side of the island, then take a break from walking and have lunch at the Southernmost Mansion.
Have Lunch at the Seaside Cafe at the Southernmost Mansion on the Sea
I’ve never stayed at The Southernmost Mansion, now known as The Mansion on the Sea, but I highly enjoyed eating at their Seaside Cafe & Bar for lunch.
The menu features classic Caribbean fare like fried conch fritters, but the real highlights are their fresh sandwiches and wood-fired pizzas. The decadent honey butter lobster biscuits are one of their signatures and, of course, there’s Key Lime Pie for dessert.
Tour the Hemingway Home and Museum
When it comes to Ernest Hemingway, I’ve met three kinds of people. Those who love him, those who can’t stand him, and those who say they’ve read his books when we both know they really haven’t. Whichever category you find yourself, there are other reasons to visit the Hemingway house that don’t involve knowing or caring about the writer.
For starters, the architecture and grounds of this home which was built in 1851 are beautiful examples of the Key West Spanish Colonial style.
Guided Tours are offered daily and typically take 20-30 minutes. After the tour, you’re free to continue exploring the house and grounds. No reservations are required and tickets are available for purchase at the main gate.
In addition to touring the house, the grounds offer interesting features as well. The swimming pool was built in 1937-38, at the eye-opening cost of $20,000. It was the first in-ground pool in Key West, and the only pool within 100 miles at the time.
The exorbitant construction costs once prompted Hemingway to take a penny from his pocket, press it into the wet cement of the surrounding patio, and announce jokingly, “Here, take the last penny I’ve got!” Visitors can look for the penny, still embedded between flagstones at the north end of the pool.
And last but certainly not least, if you’re a cat lover, then you should definitely make the pilgrimage to The Hemingway House.
There are 60 or so 6-toed (polydactyl) cats who have the run of the place. With their extra “thumb-like” toe, the cats look like they’re wearing fluffy mittens as they lounge about the furniture and flop by the pool.
“Ernest Hemingway was given a white six-toed cat by a ship’s captain and some of the cats who live on the museum grounds are descendants of that original cat, named Snow White. Key West is a small island and it is possible that many of the cats on the island are related.” ~ HemingwayHome.com
Hemingway gets most of the attention for living in Key West, but it should be noted that Tennessee Williams, Shel Silverstein, Robert Frost, Elizabeth Bishop, and Judy Blume are other famed authors who lived in Key West for a time as well.
Harry Truman also loved living on the island so much that he’s quoted as saying, “I’ve a notion to move the White House to Key West and just stay.”
Papa’s Pilar Rum Distillery
Named after Ernest Hemingway’s beloved boat, The Pilar, Papa’s Pilar Rum Distillery is located near Sloppy Joe’s Bar and features several distillery tours. The basic tour will guide you through the process of how the rum is made combined with stories of Hemingway’s adventure-filled life.
If you’re more of a cocktail person, the distillery features a cocktail-making class, and for the literary-minded, the distillery offers a “Hemingway’s Chronicles Literary Adventure.”
For current offerings and reservations, click here or the link below.
Mel Fisher Maritime Museum
Brimming with one-of-a-kind artifacts and treasures recovered from sunken ships, the Mel Fisher Maritime Museum is the place to go for history buffs or would-be treasure hunters.
In its early days, Key West prospered from salvaging valuables from shipwrecks and auctioning the valuable cargo, making it (for a time) the richest city in the U. S. per capita. The museum collection spans two floors, and touring the facility takes around an hour. The museum also features a conservation lab that you can add on as part of your tour so you can see how the items are restored and preserved.
For ticket information, click the link below.
The Key West Museum of Art & History at the Custom House
First opened in 1891, it’s really hard to miss the deep red brick building situated near the harbor of Mallory Square. If you’re interested in delving into the history of the Florida Keys and the importance of Key West, then this museum is a must-visit.
In addition to the permanent exhibits, the two floors of the museum also feature rotating exhibits with many focusing on the artists and writers who have lived and worked on the island.
If you’re interested in visiting the museum on your next visit to Key West, click the link below.
Conch Tour Train
While I’ve never hopped on myself, the Conch Train is a colorful and easy option for those who want to explore the highlights of Key West but who may have difficulty walking longer distances or those who like a guided tour option.
The Conch Tour train takes visitors on a 75-minute loop through the main areas of Key West, stopping at three key stops along the way.
For more information and ticket prices, click the button below.
Key West Water Activities
From snorkeling to parasailing to jet ski rentals or dolphin tours, Key West is a prime spot for spending time in or on its clear blue-green waters.
For those looking for an impressive snorkeling adventure, Key West’s coral reef, known as the Florida Straits, extends 150 miles north towards Miami and 70 miles west to the Dry Tortugas. It’s the largest coral reef in North America and the third largest in the world, following the reefs in Belize and the Great Barrier Reef in Australia.
For a one-stop shop for Key West water adventures, check out Sunset Watersports. They are a trusted booking company for boat rentals, reef snorkeling, sandbar dolphin watches, and even eco kayak tours.
To explore all of their watersport rentals and packages, click the button below.
Catch the Sunset at Mallory Square
Every evening in Mallory Square, visitors and locals can join in the Sunset Celebration. The festivities begin about two hours before sunset with street artists, musicians, artists, and food vendors providing entertainment.
Whether it’s your first time to this tropical creative hub on the final cusp of the Florida Keys or you’re planning a return trip, I hope this guide helps you make the most of your visit.
Safe travels and enjoy the journey…
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