Key West, Florida – soak up the southern lifestyle!

I’ve travelled all over the world, but Key West is one of my all-time favourite places and somewhere I keep coming back to. It’s beautiful, relaxed, fun, friendly and I never seem to tire of it. It’s literally the southernmost point in the continental US, only a short 90 miles to the coast of Cuba, and the last island in the string of islands called the Florida Keys. The island is a great place to visit year-round, and I’ve summarised below some of my favourite places and things to do!

Where to Stay

There’s no shortage of places to stay in Key West whether that’s hotels or Airbnbs. There are also many new places popping up in the New Town area, that seem to be a little less expensive given the distance from the Old Town. My one recommendation is to plan early and book something as far ahead as possible. The island is always busy, and places fill up all the time. If you are looking for something central and close to everything, I personally recommend The Lighthouse Hotel. It’s beautiful, has a lovely pool and is the perfect location.

Getting Around

Key West is a relatively small island, which makes getting around pretty easy. My preference is bicycle or scooter, which you can rent by the hour, day, or week. Renting a golf cart is an option but is pricier and also comes with the challenge of parking.

If you are staying mainly in the old town getting around on foot is easy, but for those less mobile there is a bus called the Duval Loop. The fare is now $2 per trip, or you purchase a day pass or a 7-day pass. This was a great option when travelling with my mom and helped us get around without having to walk from place to place in the heat.

Bars / Duval Crawl

Anyone visiting Key West will no doubt find themselves wandering up and down the main street that runs the length of the city from near the Southernmost point to Mallory Square. Along this street are a plethora of souvenir shops, restaurants and countless bars. Hopping along the various bars has become known as the Duval Crawl. I’m not necessarily advocating participating in this crawl, but if you do here are some of my favourite places to stop in!

Sloppy Joes – opened in Key West on December 5, 1933, the day that prohibition ended. Originally called the Blind Pig, Ernest Hemingway suggested renaming it after the original bar in Havana Cuba, that he used to frequent. The original location is actually where Captain Tony’s is now located but was literally moved overnight down the street in 1937 when the landlord tried to raise the rent and the bar owner refused. Sloppy Joes has become a Key West staple as a piece of living history and embodying the cities bohemian rebellious spirit.

Willie T’s – it’s very rare to find this venue not full of people enjoying live music, sipping cocktails, or just having a good time. The entire bar is decorated with thousands of dollar bills stapled everywhere and signed by the visitors who add to this décor. I think I still have a few of these located around the bar that are visible. Not only is the bar famous for their dollar bill décor and the continuous live music from open to close, but also their mojitos. This is one of my favourite spots to come when visiting.

Some of my other fave Duval sports include:

Fat Tuesdays – got to love their frozen daiquiri selections
Ricks Key West – 8 bars and one of the biggest dance floors on the Island.
Irish Kevin’s Bar – who doesn’t love an Irish bar and live music

Food and Restaurants

All the bars above do serve food as well. But some of my personal favourite restaurants on the island are:

First Flight Island Restaurant & Brewery
This building has some significant history as the birthplace of Pan American World Airways. Pan-Am’s first tickets were actually sold out of this very building in 1927, marking the first international flight in the United States from Key West to Havana, Cuba. Oh and they have some good happy hour specials, and I love their soft pretzel!!

Moondog Cafe Key West
An all-day restaurant, bakery and bar and one of the most popular spots on the island. The food is delicious, portions are large, and they have some great options for vegetarians, vegans and gluten free diets. The restaurant operates on a first come first serve basis, and there are always long lines, so get there early!

Conch Republic Seafood Company
Located right in the historic seaport is a large casual spot with some classic Key West seafood like conch fritters, shrimp and fresh catches.

Hog Fish Bar and Grill
Actually located on Stock Island, just outside of Key West. It has a very casual, tiki bar vibe, with seating right on the water. And if you want to try the local Key West catch, this is the place to come and have their legendary Hog Fish sandwich.

Key Lime pie

Key Lime Pie – it’s all in the name. It would be wrong on so many all levels to come to Key West and not indulge in this local island delight. The dessert was developed here in the 1800s using the smaller, more tart, and more fragrant small limes indigenous to the Keys. It’s now the signature dish tied to the island’s identity. There are differing opinions on where “THE” best pie is, but general fan favourites are Blue Heaven, Kermit’s Key Lime Shop, and Key West Key Lime Pie Company.

Cuban Coffee

Cuban Coffee is another must have in Key West. With the obvious close proximity to Cuba, it makes sense that the coffee became a staple on the island. It’s become so popular that the places to get one seem to have tripled since my last visit.

The most famous spot, not only for the coffee but to get a picture next to the most photographed spot on the island, is Cuban Coffee Queen. Their location on the Waterfront is the original and home to the “Greetings from Key West” postcard-style mural found on the side of the building. They also have several other locations on the island.

My other favourite is Sandys Cafe where you can also try their incredible cuban sandwich. This place has been around since 1954 and it’s quirky as it’s part of M&M laundry, so it’s like your ordering coffee and sandwiches at the laundromat.

Things to Do

Hemingway House (as well as some 6 toed cats!)

Ernest Hemingway first came to Key West in the 1920s, drawn in by the island’s warm weather, quiet streets, and laidback lifestyle. He and his second wife bought this 1851 home and carried out extensive renovations to bring it back to life. Today, the house is wrapped in tropical gardens and shaded by wide, wraparound verandas. They even installed the island’s first inground swimming pool; a project so expensive that Hemingway joked it cost his “last penny”. And you can even find a pressed penny in the concrete in front of the pool. Inside, you can wander through his preserved writing studio and the rooms he once lived in.

There are also the famous six toed cats, descendants of Hemingway’s own, who roam the property like they own it. There are 61 of them, and they’re federally protected.

The home is open every day, and tickets are $19 for adults. Get there right when it opens to beat both the crowds and the heat.

Shipwreck Museum

The Key West Shipwreck Museum is located near Mallory Square and offers some great insight into the island’s early days. Housed in a replica 19th century warehouse, the museum tells the story of Key West’s shipwrecking era, which is a time when wreckers made their fortunes salvaging cargo from ships that ran aground on the reefs. Inside, you’ll find artifacts pulled from real wrecks, dramatic storytelling from costumed guides, and a lookout tower you can climb for some of the best views in Old Town.

My interesting takeaway here is that during the height of the shipwrecking era, Key West was one of the wealthiest cities in America. It’s part history lesson, part immersive theatre, and a fun way to understand how shipwrecks once shaped the entire economy of Key West.

If you are also planning to visit the Aquarium and perhaps a ride on the Conch train, buy a combined ticket to save a bit of money.

Key West Aquarium

Built in the 1930s, Key West Aquarium is one of the island’s oldest attractions. It gives you an up-close look at the marine life that surrounds the Keys, such as stingrays, sea turtles, and sharks. There’s also a few touch tanks where, at certain times of day, guides explain the sea life inside and let you gently handle some of the fascinating creatures. While especially fun for kids, I found it pretty cool myself. I mean it’s not every day you get to hold a horseshoe crab or feel a sea cucumber. The aquarium is small, simple, and a little nostalgic, but that’s exactly what makes it such a sweet slice of Key West history.

Conch Tour Train

The Conch Tour Train is an easy and enjoyable way to explore Key West, especially on those hot, humid days when wandering the island on foot feels a bit much. Running since 1958, the train winds through the Old Town’s narrow streets while guides share fun stories about the island. It’s a relaxed, breezy ride that gives you a great overview of the city without the miles of walking. Plus, the hop on, hop off style makes it easy to explore at your own pace.

The Key West Butterfly & Nature Conservatory

This feels like a quiet oasis tucked right off Duval Street. Inside the glass enclosed habitat, there are hundreds of butterflies floating through lush tropical plants, waterfalls, and winding pathways. You’ll even find flamingos wandering the space too. Stay still long enough and you will become a landing spot for some of the butterflies. Just be sure to check yourself before you leave so none of these little guys hitch a ride out with you.

The conservatory is cool and peaceful, and a perfect escape from the heat. Also a great option if you’re looking for something relaxing that doesn’t require much walking.

Key West Gardens at West Martello

Built in the mid 1800s as part of the island’s coastal defences, the fort was never completed, but today it’s weathered brick arches and open courtyards have been transformed into a beautiful garden space maintained by the Key West Garden Club. Wandering through the pathways, you’ll find tropical plants, quiet nooks, and stunning ocean views framed by the old fort walls. It’s a calm, breezy spot to explore, and a lovely break from the busier parts of the island.

Kayak through the Mangroves

For a peaceful yet adventurous experience why not try kayaking through the mangroves. There are a few options in Key West, but one of the most popular is Lazy Dog Adventures at Hurricane Hole Marina.

Mallory Square - sunset celebration

Mallory Square is at the island’s northwest edge, by the cruise ship docks and harbour. It’s most famous for the nightly “Sunset Celebration” ritual. Crowds gather to watch the gorgeous sunset over the Gulf of Mexico. There’s also street performers, food vendors, and artists. Its a must do on at least one evening here.

Southern Most Point - or is it?

The most photographed spot on the island. This painted buoy marks 90 miles to Cuba and the Southernmost point in the continental United States. However, it’s actually not the exact spot of “the” southernmost point, as that is located on a nearby Naval base, which is obviously not open to the public. So, this is the next closest spot to get that quintessential photo! Get here early as from mid-morning onwards you’ll bewaiting in a line to get this photo! I personally loved stopping her on my morning runs for a shot of the buoy and the sunrise in the background.

Beaches

Higgs Beach

Higgs Beach is on the south side of the island, facing the Atlantic Ocean close to the historic Casa Marina area. It is one of the main public beaches in Key West, but is more laid-back, local, and activity-focused. It’s got free parking, restrooms, showers, and a great beachfront cafe called Salute!

Fort Zachary Taylor Historic State Park (“Fort Zach”)

Of all Key West beaches, Fort Zach is my personal favourite. It’s located at the southwestern tip of Key West, where the Gulf of Mexico meets the Atlantic. The small entrance fee (upto $6 for a vehicle with up to 8 people) covers everything: beach access, snorkelling areas, picnic spots, and entry to the historic fort.

The water is really clear, so great for snorkelling. There’s also a small cafe, loungers and umbrella rentals. I can’t think of a time I’ve not been here when in Key West – it’s just so beautiful and definitely the most scenic beach on the island.

Smathers Beach

Smathers Beach, on the south of the island, is the largest and most popular beach in Key West. It has white imported sand and is a hub for water sports like jet skiing, parasailing, banana boats, kayaking and paddle boarding. It has more of a party vibe and can get quite busy during the day.

Smathers, Higgs and Fort Zach are the big three beaches on the island, but there a few smaller ones worth noting too:

South Beach: small but central and popular
Rest Beach: quiet, good for sunrise, not great for swimming
Dog Beach: very small and as the name suggests…very dog friendly
Simonton Street Beach: tiny sandy patch, easy access

Fantasy Fest

I would be remiss if I didn’t talk a bit about this 10 day festival in Key West. Fantasy Fest takes place in mid to late October, leading up to Halloween. It’s basically Key West’s version of a wild island carnival + Halloween party + street parade all rolled into one. While there are some kid friendly activities, it’s definitely more of an adult only event. But if you like dressing up, or as the Brits say fancy dress, then this is the place for you.

Venues hold daily themed events that allow for creativity with costumes, body paint, you name it. It’s not for the prude or conservative types though, as you will see just about everything on display. Having said that, you can just enjoy on a more casual level if you want.

I’ve been twice and it’s such a fun time, I’m definitely planning on a third visit in the near future!!

Wrap Up

From sunrises on the beach to sunsets at Mallory Square, the island way of life sets in as soon as you arrive. Whether you go for a short visit or a stay for a 10-day long festival, Key West has plenty to offer! I never tire of this beautiful place, and I’m sure you won’t too!