It took only a couple of days for me to fall in love with Key West, the tiny island at the bottom of the Florida Keys in the US.
I loved the people, the architecture, the laid-back lifestyle, the fun, almost-anything-goes vibe, the warm climate.
I loved that you could ride a bike anywhere with the wind in your hair and a strong scent of freedom in the air.
I arrived with very few expectations and the bohemian nature of the island swiftly seduced me. It’s a mix of hedonism, history and a little bit of highbrow.
Key West draws people from all over the US, many dropping out of the mainstream, attracted to the slower pace of life and the laissez-faire lifestyle. The locals are relaxed and friendly, secure in the belief they’ve landed in paradise.
The best way to get to Key West
Getting to Key West is half the fun. While you can fly to this southernmost part of the USA, it’s much more spectacular to drive along the famous Route 1, the Overseas Highway that connects the Florida Keys via 42 bridges. One of the bridges is seven miles long.
It’s a stunning 113-mile drive along the highway with the Gulf of Mexico on one side and the Atlantic Ocean on the other. Some of the bridges arch high over the water; elsewhere, the water laps the shoreline only a few feet from the road. You realise how low-lying this area is and why it’s so vulnerable to storms and flooding.
Best things to do in Key West
Key West has a colourful reputation. It’s famous for its annual Fantasy Fest which includes Tutu Tuesday – yes, everybody gets dressed up in a tutu – and a clothing optional day where most people get dressed up in body paint. That’s it, just body paint.
There’s a super touristy part of Key West that’s knee deep in not-so-swanky bars and cheap souvenir shops. It’s not my kind of thing though there were plenty of people who loved this end of Duval Street, the famous strip of bars and restaurants that runs from one end of the island to the other.
We barely spent any time at this end of town. Instead, we explored all over the island, cruising around on rental bikes, even though parts were still being cleaned up following the damage caused by mega-storm Hurricane Irma.
So, what are the best things to do in Key West?
#1. Hire a bike to cruise around the island
By far the easiest way to get around Key West is by bike. It’s so flat and there are bike lanes all around the island. The whole island is only about four miles long (6.4km) and one mile wide (1.6km).
There are loads of bike rental shops and most visitors opt for a comfortable cruiser. Because we wanted to ride around the whole island we got hybrid mountain bikes. We picked up ours at Eaton Bikes, which had some fabulous bike paraphernalia, some of which we had to buy to bring home.
It’s not compulsory to wear a bike helmet in Florida. I was a little nervous about riding without one at first, but I soon got used to it and loved the feeling of freedom. Where the roads were busy and we felt unsafe, we just jumped up and rode on the footpath.
#2. Visit the home of literary legend Ernest Hemingway
Even if you’ve never read any Hemingway I’m sure you’ll be captivated by the stories of his life as you tour his grand Key West estate. It’s quite the compound with a large, glamorous house that’s been carefully preserved, extensive gardens and swimming pool.
Hemingway lived here in the 1930s and you can peer into his writer’s studio where he created some of his most famous works.
Hemingway was a larger-than-life character who had four wives. He was a bon vivant who lived an indulgent life. He loved a drink and was a hunting, fishing and shooting kind of guy. The tour guide brilliantly brings the charismatic Hemingway to life exposing his flaws, failings and flamboyance.
The house is also famous for the dozens of six-toed cats that roam the grounds. There are more than 50 of the polydactyls that date back to Hemingway’s days.
This grand estate is now a popular site for weddings and events.
#3. Tour President Truman’s Little White House
From the home of a literary legend to the winter house of 33rd American President, Harry Truman. The Little White House was originally the naval station’s command headquarters during wartime and became President Truman’s winter White House when the doctor ordered him to take a holiday from the cold Washington weather.
The Little White House is now a museum and has been meticulously preserved exactly how it was when the President spent his winters here in the 1940s and ‘50s. It’s part of the picture-perfect Truman Annex neighbourhood in Old Town Key West, where most of the houses are white and very orderly. It’s worth having a snoop around the estate.
#4. Admire the architecture and historic homes
We stayed in the stunning Marquesa Hotel on Fleming St, a beautiful old weatherboard home that’s been converted into upmarket accommodation. There are so many historic homes in this neighbourhood and many have been transformed into quaint hotels. We loved wandering the streets, admiring the romantic old mansions, daydreaming how lovely it would be to own a slice of Old Town Key West.
Whatever you do, don’t stay in a big chain hotel in Key West. These soulless multi-story buildings seem so out of place here. Look for a character-laden historic home around Fleming and Eaton Streets.
#5. Climb the Key West Lighthouse
The Key West Lighthouse is just across the road from Hemingway House. If you’re feeling energetic climb the 88 stairs to the top for panoramic views of the town. It’s a great way to get your bearings.
I’m a little scared of heights and while I had no problem with the steep and narrow stairs, I was a little anxious in the strong winds at the top.
#6. Snap yourself at the southernmost landmarks in the USA
The southernmost point of the USA is in Key West. It’s such a cliché to photograph yourself at the landmark here but hey, you’re a visitor so it’s compulsory!
The point was being repainted when we visited, undergoing repairs post-Hurricane Irma, but that didn’t stop anyone from getting a photo around the fencing.
We also took a snap at the other significant endpoint – the end of US Route 1, the 3,800-kilometre highway that runs down the east coast from the Canada-US border all the way to Key West.
#7. Swim at Fort Zachary Taylor beach, Key West’s best beach
Smathers Beach may be the biggest and best-known beach in Key West but locals reckon the beach at Fort Zachary Taylor in the national park is the best. It wasn’t a spectacular day when we went, plus some areas were closed off because of damage from Hurricane Irma but you can appreciate its appeal.
Fort Zachary Taylor is a small, secluded, pretty beach surrounded by leafy national park. It’s a nice ride through the park to reach the beach and there are a couple of walking trails to meander down.
It costs a couple of dollars to get into the national park.
#8. Stuff yourself silly with delicious key lime pie
There are some great restaurants and excellent food in Key West, however, we were on a quest to find the best key lime pie. Everyone claims the title and we fattened up a little thanks to our campaign. I had key lime pie for breakfast, lunch and dinner one day!
And the winner is…
Our favourite key lime pie came from Mattheessen’s on Duval St, just around the corner from our hotel. I’m not sure why it was the best, maybe the thick graham cracker crust and rich creamy pie filling. Or maybe it was the generous servings that won over my sweet tooth. Mattheessen’s also made drop-dead delicious cookies and fudge. Yum!
#9. Mallory Square
Mallory Square is the number one tourist attraction in Key West. It’s the epic sunset-viewing location where everyone gathers at dusk to watch the sun go down over the horizon.
We avoided the evening crowds and cycled by during the day when it was almost deserted. There’s a beautiful view over to Sunset Key, an upmarket neighbourhood of Key West.
Mallory Square is also where the big cruise ships dock and it’s quite a spectacular sight wandering beneath these giant ships.
#10. Key West Butterfly and Nature Conservatory
My travel buddy JJ was very sceptical about visiting the butterfly conservatory. He’s not much of a museum person and didn’t want to pay another entry fee. (We’d already done Hemingway House, Truman’s Little White House and the Lighthouse).
However, the Butterfly aviary came highly recommended from one of the locals. It was pretty amazing to wander around the conservatory and have colourful butterflies flitting by your face. The two flamingos put on a good show – I’ve never seen one up close before and their feathers are stunning.
JJ was underwhelmed to say the least and thinks it’s best suited to kids. You decide.
Colourful Key West
If there’s one word you’d use to describe Key West, it’s colourful, in every sense of the word. It’s possible that I fell hard for Key West because I had very low expectations. Sometimes travel works out that way: disappointment at the places you’re most excited to visit and surprise and delight when you least expect it.
Let’s hope I haven’t spoiled the surprise for you.